Young Josh went away to college with no friends, plans or dreams for his life. It all comes together for him as Jill but not until a terrible tragedy changes his life.

A Tragic Beginning
by: Teresa Ann Wood

Of course I felt guilty; the opportunity of a lifetime had come to me and even if it turned out to be better than even my wildest dreams that wasn’t the way I had wanted it to happen. I never wanted to profit from someone else’s tragedy.

My name is Josh Benning and I have been a closet crossdresser for most of my young life; living out of the clothes hamper of my female relations and those of my few friends. I was never caught, not once, in all those years of dressing up but that was mainly because I was so cautious. I never once left the bathroom, not even when I knew that I was home alone. I was a coward but with good reason; I’d seen what my father did when my older siblings broke his rules and none of them had ever done anything that would be as bad in my father’s eyes as a boy wearing girl’s clothing. I wanted to dress up, but I wanted to live too.

Anyway I kept my secret all the way through high school and did my best to live a ‘normal’ life in public. I asked out some girls only to be turned down as I was small and apparently completely unattractive to them. I didn’t know why their negative responses were such a relief to me. I thought that I was just scared of going on that first date; I wouldn’t know what to do, how to act, but it reality I just didn’t want to date a woman. Even then I was gay; I just hadn’t admitted it to myself.

My family was poor but I had good enough grades to earn a scholarship to an in-state college. It wasn’t a huge school with tens of thousands of students, but it had enough to maintain most of the major sports teams like football, basketball, baseball, and even soccer. They offered sports scholarships but most were not full scholarships; leaving most of the students to come from very wealthy families. They had a gymnastics team, the only sport I could compete at, and so I had intentions of trying out for it when I got there. My dad wasn’t crazy about it but he was mollified that his ‘sissy’ son was at least going to be competing in a college sport. None of my behemoth brothers had accomplished that.

So off I went, moving from my small rural high school to a community that was just barely large enough to qualify as a city. Lendersville had a population of around 35,000 people, most of which had jobs that were at least indirectly reliant on Lender College. It was a college town, that’s for sure, and all incoming freshmen were made to feel right at home. I certainly was, at least until I met my roommate.

Trent was a conceited jerk, no question about it. In his heart he knew that he was incredibly handsome and the wet dreams of every young woman he met. He was an athlete at Lendersville on a basketball scholarship. At six-foot-three he may have been tall for a point guard, but his ball-handling skills were superb. He had offers from bigger schools but chose Lender College because his family had some sort of legacy there; every one from their family had attended Lender for a hundred or more years, apparently. Trent wasn’t necessarily a cruel guy, but he realized right away that he was the dominant male between us and he simply expected me to do what he said. The worst part of the whole situation was that Trent was every bit as dreamy as he believed, and for the first time I could not deny my attraction to another man. He was mouth-wateringly gorgeous!

As I was planning on trying out for the gymnastics team, I had to arrive at school several weeks early. Trent was already there and before the first week was up I was the one responsible for cleaning our dorm room. I tried to make the best of it and would try to do it when he was gone, so I could slip on a pair of panties (the only female attire I owned and all I dared to keep with me) beneath my regular clothes and pretended to be a woman cleaning the room for myself and my boyfriend (I had it so bad for Trent). I really enjoyed picking up his dirty clothing, particularly his jockstraps, and before long I was doing both our laundry too. In some ways I didn’t mind too much but in others I did; but one peek at his half-clothed body would drive that away. Just about anything was acceptable if it kept us living together; he was so hot! Before long I found myself masturbating daily thinking of him, but unfortunately had never had a chance to catch a peek at his cock. I couldn’t take the chance that he might catch me looking.

Anyway I went out for the gymnastics team, just like I planned. I worked hard for three weeks but in the end I was the last one cut; I had the ability, the coach said, I just didn’t have the experience of the other guys. This was devastating to me since I had really wanted to make the team; not only did I want my father to be proud of me (I’m not sure why) but since Trent had convinced me that I was, in fact, truly gay, I enjoyed the sight of the other male gymnasts dressing or showering after practice. This led to another epiphany for me; I was pitifully endowed.

My dick is tiny, no question. I knew it was smaller than average from some ‘research’ I had done on the internet but I had convinced myself that those men were on there because they were so much larger than normal. Perhaps they were, but even average is apparently far bigger than me. I’ve begun to think of my dick as ‘the smallest in captivity’, as even at full erection I can easily jack-off with two fingers. None of the other gymnasts could match the monsters of the internet, but then again even the smallest of them made an easy three of me. I made sure they didn’t see mine even as I took cautious peeks at theirs.

Needless to say I was really downhearted about not making the team, and dreaded having to tell my parents as I knew my dad wouldn’t take it well. I didn’t have to worry about that, because by the time I went home that next week to break the news; he had died of a massive heart attack. This was devastating to my whole family, even to me; my dad and I didn’t always get along but I knew he only wanted what was best for me in his eyes. Our determination of what was best simply varied too much. He had loved me in his own way, I know that.

I returned to school right after the funeral not because I had to, classes still didn’t start for a long time, but because I wanted to. Home was too depressing, particularly with mom grieving like she was, and I wanted to get back to Trent. Not that he had missed me; he only knew I had been gone because the room hadn’t been cleaned; his days were filled with pickup basketball games and chasing various unattached women. Once I had told him about my dad, however, he became nicer to me and listened as I talked about my grief. It’s amazing what will strike a cord within someone. His own father had died not long before, and that was part of the reason he had came to Lender. He comforted me that first night, not in his arms like I wanted, of course, but we talked most of the night. I loved him all the more for it.

One positive side of my father’s death was that I no longer had to worry quite so much about doing some things that I wanted to; such as letting my hair grow. I had let it grow as much as he would allow before leaving for college and hadn’t touched it since I got here. I was intending to cut it before going home but his death caused me to forget. Now I wouldn’t have to cut it if I didn’t want to; mom wouldn’t care. It grew pretty quickly anyway and so I hoped that by the New Year it would be long enough to reach my shoulders. It was a secret dream of mine to have hair long enough to wear in a ponytail. Certainly it was a feminine hairstyle and yet I could get away with wearing it in public! For me, that was a very brave plan. Who knew if I would ever have the guts to go through with it but I could at least let it grow for awhile to feed the dream. Another positive aspect came a day or two later when I read a notice concerning cheerleader tryouts. There were no scholarships for the cheerleaders so the tryouts were completely open. My heart almost stopped when I realized that I could tryout for the cheerleading squad.

What was stopping me? My dad was gone, he would never have allowed that, and in college there were male cheerleaders all the time. It didn’t carry nearly the stigma that male high school cheerleaders did. Not that my high school would have ever have allowed such a thing. Perhaps I couldn’t make the gymnastic squad, but those same skills just might get me onto the cheerleading squad! Tentatively I mentioned my idea to Trent, who thought it was a great idea.

“You get to look up the cheerleader’s skirts all the time; and they sit right on the palm of your hand when you lift them up in the air,” He chortled. “I would love to be a male cheerleader; they’re bound to get laid all the time if they’re not all queer.”

Trent’s comments emboldened me even as I worried that they were hitting too close to home considering the ‘queer’ comment. He had given me an obvious excuse as to why I wanted to be a cheerleader but even so I was amazed that I had the guts to even consider it. Despite telling myself that I would never go through with it and that it was simply a nice little dream to play around with I found myself in the gymnasium on the first day of tryouts.

I was surprised to see fourteen guys trying out for the four open spots on the squad. There were twice that many girls trying out for only three openings on the girl’s side. At least half the guys were there for the same reasons that Trent had given; they just wanted to get their hands on the girls and so they were quickly weeded out. My tumbling skills got me invited back for the second day but by then it was obvious to me that I simply did not have the strength to do what they needed. I had to be able to lift the females and hold them over my head; it was they who needed the gymnastic skills not the men. Somehow I was invited back the third day with four other guys; I had an eighty percent chance of making it, but at the end of that day the cheerleading coach took me aside and gave me the bad news; I had been cut.

“We’ll keep your name on file, though,” she said, patting me on the shoulder. “If we have an injury we might use you to fill in for the alternate we activate.”

Great. I couldn’t even make it as a full-time alternate. I thanked her and gathered my stuff, delaying as much as possible in the hopes that the other male cheerleaders would come in to shower once more before I left, but I was disappointed in that regard. Most of them were gay just like Trent had joked but for whatever reason those guys didn’t really appeal to me. Not like Trent or the other straight guys did, anyway. When I looked at him, I was immediately aroused. When I looked at the obviously feminine-acting gay men I felt absolutely nothing. At least with women I had some interest in what they were wearing.

I sulked as I left the locker room; apparently college was to be no more successful for me than high school had been, at least not outside the classroom. Most of the gymnasium we had been working out in was empty, the door to the track stood open so they must have been outside running but I noticed one figure sitting near the top of the bleachers on one side. The noise from outside was too loud for me to hear anything but I could tell by the way she was sitting that she was crying. Without thinking too much about it I made my way up the steps to her, approaching quietly so as not to frighten her. That was almost funny to me; no girl was ever frightened of me; I’m smaller than them more often than not. I sat nearby but not threateningly close. I wanted to help but if she didn’t want to speak to me then I would leave.

I recognized her of course; she had been trying out for the cheerleading squad as well, though they had scrupulously kept the men and women apart during most of the tryouts to discourage the horn-dogs that were there just to get a peek up a few skirts. She was quite pretty with red hair and a petite build; she was barely taller than me which was saying something. She had a nice, athletic body and I had thought that she was a shoo-in for the squad. I guess that showed how much I knew. I sat for awhile and was just about to leave when she finally spoke.

“I guess you were cut too,” she sobbed, never once lifting her face from her hands.

I said that I had been and tried to ask her the same question but of course it came out all messed up. Thankfully she was merciful and didn’t take me the wrong way.

“Yes, and it’s not fair! I deserved to make the squad!” she grouched, finally lifting her face and looking at me, daring me to disagree, I supposed.

“I totally agree, you were great,” I said quickly, not wanting to have ‘beaten-up-by-a-cheerleader’ attached to my already weak reputation.

Mollified she calmed down a bit and we began to talk about the unfairness of her plight. I really did agree; she was easily as good at cheerleading as any of the girls that made the squad, and so she found some comfort in my presence. I actually felt better about my own failure as well, just by helping her. That seemed odd to me at the time but I understand it now.

“Do you know why she cut me?” the girl, her name was Debi, demanded at one point. I said no. “Because she’s a lesbian and she only wants girls with big boobs!” she explained, tugging her t-shirt tightly to her body to expose the outline of her breasts. “Do you see anything wrong with these?” she demanded again, glaring at me as if daring me to say that I did. She certainly had the temper to match that hair.

I dutifully looked at the small mounds on her chest, noting that they were likely B-cup unless her clearly visible sports bra was messing with my judgment. Certainly not huge breast but I would love to have them myself.

“No, of course not, they’re great,” I stumbled, looking away from her chest in embarrassment. Had I really thought that I would like to have breasts like hers? “But how do you know that’s why she cut you?”

Debi laughed once, very sharply. “It’s a well-known fact that she’s a lesbian. She was almost fired two years ago for dating one of her cheerleaders. This is my fourth time trying out, and I’ve been the last one cut every year. Now I’m a senior, and this was my last chance. It’s so obvious that she only wants girls with big tits on her squad; if you pay attention to the ones who make the team you’ll see what I mean…” she hesitated, looking a little closer at me.

She suddenly moved closer on the bench, staring intently at me. Not in a threatening way but just very intent. Catching my eyes she also caught my own gaze; I was staring eye to eye at her without the least ability to look away. She was looking into my soul, that’s how I see it now, but then it was very disturbing to say the least. Even in her sorrow she wanted to help me in return.

“You’re gay, aren’t you.” She stated matter-of-fact. My gaze was still captured by hers and I was the only one of us who was surprised to hear my voice say that I was. Perhaps some people might have suspected but no one actually knew. I was mortified over what I had just done!

“Don’t worry, I’m not making fun of you,” she said quickly as she scooted even closer to me on the bench-style bleachers. “I know it had to be tough on you to be cut as well. I can imagine how much you were looking forward to showering with all those cute guys.”

She was teasing me, and for the first time in a life filled with teasing it didn’t hurt; it even felt good. Tearing up myself I shared a little laugh with her and within an hour we were the best of friends.

We spent the next several hours drinking coffee at a little diner and then went back to her dorm until I and any other men visiting had to leave. Then we walked for a while around campus just talking; it was a wonderful evening and completely new to me. I’d never had a close friend and Debi was wonderful. We talked of our disappointments and I talked of being gay and a virgin. She told me about her past boyfriends and her desire to be a cheerleader. Debi promised not to tell anyone about my being gay and for the first time in my life I was able to unburden myself completely. By the time I went back to my own dorm she knew everything there was to know about me; even my desire to crossdress. We agreed to meet for lunch the next day and I could barely sleep I was so excited. Scared and excited. I had told her everything, all my secrets, and if she had been playing me for a fool everyone one campus would soon know. By the time I drifted off to sleep I was frantic with worry. How could I have been so stupid?

But she met me for lunch just like she promised and within minutes I knew that she hadn’t told anyone about my secrets. Indeed I felt that she would never betray me that way and by the time we finished lunch it was almost time for dinner and she had shared such intimate details of her own private life that I knew that my secrets would always be safe with her. Whenever we were alone she started calling me ‘Jill’ but never forgot to call me ‘Josh’ when someone else could overhear.

After dinner we went back to her dorm again, her roommate had not yet arrived for fall classes, and she showed me a smooth plastic dildo she kept locked in her makeup case. She told me about her sexual encounters and confessed that she used the dildo ‘more often than she had to’ because she had never had trouble getting a boyfriend. She told me about giving head, she didn’t enjoy it but had done it a few times for guys she really liked, and told me how wonderful it felt to have her pussy stretched wide by a nice, thick cock and feeling it rubbing against her clit. Naturally this sort of talk turned us both on and after sharing these sort of intimate conversations all that next week it seemed only natural for her to use the dildo on herself in front of me as she explained what felt the best. By the third or fourth time I was even helping her; working the dildo in and out while she played with her clit or cupped her breasts. Sitting through these sessions without even getting hard was the last straw as far as removing my last denial about being gay. I never got excited until she offered to let me try her dildo for myself.

Scared, embarrassed, and surprised, I declined her offer but she wanted to do something for me and so the week before her roommate arrived she finally convinced me to allow her to dress me up completely as a woman; makeup and all, just so I could get the full experience. I was so nervous I almost passed out but I showed up when she told me to, fully shaved from eyebrows to toes, and enjoyed a glorious evening trying on her clothes. We were very nearly the same size, even her bras fit me perfectly though I couldn’t fill the cups, and I must have tried on every outfit she had twice over. I adored her stockings and when I left that night she insisted that I wear a pair of pantyhose home ‘just to get used to them,’ she giggled. We did this every evening until her roommate arrived and I graduated to wearing her panties full-time. Not easy to keep out of Trent’s sight but I managed it well enough. That last weekend we went shopping together, me dressed as a man except for my panties, and she bought a lot of clothing for me as her family was wealthy and she had her own charge cards. She kept the clothes in her dorm for me but with her roommate due to arrive soon we both knew that my dressing opportunities would soon end. That was when she got the news.

Lender College had a mascot, like all colleges I guess, and ours was a Puma. It was a big, angry looking feline with a trademark LC ball cap on its head. Naturally images of it were everywhere on campus, complete with such statements as ‘Puma Pride’ and ‘Go Pumas’. Debi’s roommate had arrived and classes were only a day or two away from starting when Ms. Chlebowski came to see Debi and offer her a place on the squad. She wasn’t nearly as excited as I thought that she would be.

“The mascot?” she grouched. “I don’t want to wear that stuffy old costume, that’s not real cheerleading!”

“Yes it is,” I argued, sipping at my coffee. The diner had become our regular hangout now that her roommate was there. “It may not be the same as having some guy’s hand up your butt all day but you’re still cheering your team on to victory!”

That at least made her giggle and eventually she accepted the position. It certainly wasn’t her dream but finally she agreed that it might be fun but only if I agreed to attend every game that she did. I agreed, what else did I have to do? Study and watch her was about it. I still had no social life that didn’t involve her. Trent thought we were dating as it was.

So Debi became the new Lender College mascot, dressing up in that ratty old puma costume and practicing for hours each day as ‘Lendy’. Fall classes began in mid September but the first football game was more than a week before that. She had to attend all the home games for football, basketball and soccer for both the men’s and women’s programs and had to at least make three appearances each for softball and baseball in the spring. That was far more than the regular cheerleading squad had to do, as they were only required to attend home games for football and basketball plus their own ‘cheer’ tournaments. Being such a small university, we didn’t have varsity and JV cheer squads, nor a pep squad and the like to handle all the sporting events, and only one mascot suit as well. By halftime of that first football game, we lost something like 37-17; I knew that Debi enjoyed being Lendy a great deal.

Now Debi had more demands on her time but she still made room for me. I came over and helped her with her homework, even though she was a senior and I was a freshman, I was a better student that she was. I didn’t always know as much about her subjects but my research skills were impeccable. Whenever her roommate Abby would leave on a date Debi and I would talk about men and clothes. She agreed that Trent was a total cutie, and she would always offer to dress me up. I wouldn’t, afraid that Abby would return unexpectedly, but Debi would still find ways to help me by practicing her own makeup skills while I watched and asked questions. She would also insist that I wear the ‘proper’ underwear while visiting, helping me put on a bra to go with the panties I always wore now. Feeling that sweet tightness across my chest while Debi and I talked about the cuter guys on campus is one of my fondest memories. She would occasionally urge me to ‘come out’ and offered to introduce me to some other gay friends but I always refused. At heart, I was still just too much of a coward despite the thrills these conversations gave me.

My life became very busy as well now that classes were in full swing and I still had to keep my dorm room clean while doing mine and Trent’s laundry (I always thought of it as ‘our’ laundry) along with most of his homework with my own as well as being there for all Debi’s appearances as Lendy and visiting her as often as possible. Debi only came over to my dorm a couple of times but decided to stop when Trent started hitting on her. She said that while he was hot she would never steal a man away from one of her girlfriends. Debi always knew what to say to make me happy.

Wearing that mascot costume was hard work, particularly in the fall once football and soccer were in full swing. Neither sport had really slacked up very much when basketball was starting up so Debi and Lendy did not make every game, sometimes she had to prioritize, but she made a great effort at it. Several times she had to attend multiple sporting events on the same day and she would always come home exhausted. I was at every one that I could be at and gave her long massages afterwards to ease the cramps in her muscles. Obviously she was in great shape to maintain that sort of activity and I enjoyed rubbing the kinks from the muscles of her nude body.

I always wore a minimum of panties and bra when I did so and it was fun and easy to pretend that I was her girlfriend. If Abby wasn’t around I would sometimes use Debi’s dildo on her, she didn’t have much time for dating, and by now I knew just exactly how to tease her clitoris to ensure that she had a good orgasm. She would occasionally again offer the dildo to me for my own use but I continued to refuse. Not even when she offered to do me by hand would I agree to masturbate in front of her. I was both ashamed at my smallness and by the fact that I wasn’t a woman like her but she persisted until the weekend before thanksgiving when she caught me in a truly vulnerable moment.

Abby had gone home for the weekend, so I had allowed myself to be dressed completely for the first time since the semester began. I was in heaven as Debi and I sat together, giggling over boys and trying on various dresses and outfits. I should have realized that something was up when Debi pulled out a stack of brand-new magazines, bought just for me and that occasion I later found out, that were dominated by pictures of nude, handsome men. Two were recent issues of Playgirl and two others were Club magazine. The Playgirls were nice, the men were certainly hot, but their cocks were always soft. They stirred the imagination but didn’t really turn me on as much as the other mags did. The Clubs were primarily full of naked women but there was one blazing hot pictorial in each that featured a woman or women with a rock-hard stud busily working to fill their mouths and snatches. I was mesmerized by the pictures, just as Debi planned, and when she started making her offers I soon gave in.

Lying back on her bed she had me hold the magazine open to a particularly torrid picture showing a tight close up of an amazingly large and erect cock. To either side were the lips of two women, their tongues plastered to the sides of that beautiful dick, captured in mid-lick. Debi handed me her dildo, insisting that I kiss and lick it while imagining that at least one pair of those lips licking that magnificent cock were indeed mine. Lifting my skirt, Debi talked about how wonderful the guys said that I was at sucking cock, particularly Trent who had told Debi that I, Jill, was the best cocksucker he had ever known. All patently false but the fantasy worked like a charm and she barely had to squeeze my miniature cock through my panties twice before I erupted in the best orgasm I had ever had.

That night was amazing. Debi convinced me to hide in her closet when the dorm monitor checked the room and then I spent the night in bed with her dressed in her sexiest nightgown. I used the dildo on her twice, I even licked her clit although I really didn’t enjoy it, but she said that I could pretend that it was a little bitty cock. That didn’t really work but I didn’t mind doing it for her. She jacked me off twice more by morning and I was amazingly happy all the next day despite being exhausted. Debi added to my happiness by convincing me to wear a complete set of women’s underwear beneath my clothing; a girdle, slip and stockings to compliment my usual bra and panties. She explained that since I didn’t have classes on a Saturday and it was cold enough to wear a thick jacket that no one would ever know. They didn’t, but I did, and I was both frightened and exhilarated all day. I didn’t dare go back to my room dressed that way, but otherwise it was fantastic. When I did get back that evening after changing into a more modest pair of only panties beneath my jeans, even Trent commented that I seemed to be in a better mood than usual.

As the semester wound down the football and soccer seasons ended, we didn’t have a winning record and so no post season in either sport, leaving only basketball still going on. Trent and the men’s team were doing fairly well, they had at least won more than they had lost, but the women’s team was something like 0-12 going into conference play. Debi had gone to the football homecoming with a football stud named Darren and had continued to date him through December. I was more than a little jealous but then she gave me a picture of his cock at full staff and I forgave her. It was really nice and I certainly couldn’t deny her that kind of pleasure. I hid the picture well, but I couldn’t help taking it out when I was alone and pretending that it was Trent. Everyone was preparing to go home for Christmas break when the tragedy struck.

It was a typical college party; too much drinking and a bunch of people too young to handle it. Darren and Debi had double-dated with Abby and her latest boyfriend, she was a real slut it seemed, and Darren had drunk entirely too much alcohol. Abby called me from the hospital, babbling about Darren driving like a crazy man and hitting a tree. Debi was the only one who died.

The campus mourned, of course, but not like I did. I called home and told mom what had happened, she knew about my close friendship with Debi and likely believed that we were dating. I told her that I wouldn’t be coming home for Christmas; I really needed to stay here and sort out my feelings. She gave me no problems about it and I just lay sulking in my room for the first several days. When the dean of the college asked me to box up Debi’s things to send home, I couldn’t say no.

Abby had taken Debi’s death hard as well, and had not only gone home but withdrew from Lender College as well. They had roomed together for four years and done a lot of crazy things together. She had packed a few things but had left a lot of her stuff behind, and all of Debi’s remained where she had left it. Naturally I couldn’t very well send home everything; Debi’s dildo for instance, nor the magazines that she had really bought for me, so I was careful about what I packed. I was about halfway through and starting to look through Abby’s stuff when I found a letter from Debi’s parents. They asked that Abby send a few specific things home to them and then donate all the rest of Debi’s things to whatever charity she wished. They were too distraught to handle very much and wanted only a few cherished keepsakes. Unsure what to do I continued to pack up everything in the room, including the clothes that really belonged to me, and simply stacked them up in the closets. I mailed the things that Debi’s parents wanted but the rest I left in the boxes. I had no idea who to donate them to and wasn’t sure that I wanted to. The dean said that he understood the problem, or at least thought that he did, and that I shouldn’t be in any real hurry to get rid of the clothes. I had until the next fall to find a suitable charity to donate them to as the dorm room would remain open until then. The hardest part of the whole process was finding a present addressed to me on Debi’s top shelf. I very nearly lost it then.

I stopped wearing panties for a while. It was just too painful because all that I had had been given to me by Debi. I sulked around for days, spending all my time in Debi’s room, just lying on her bed and crying. When Trent came back after the holiday, he found me there. He sat beside me on the bed and even put his arm around my shoulders. I leaned into him and cried some more; not even turned on by his touch I was so miserable. After crying for what seemed hours, I realized that I had unconsciously wrapped my arms around his waist as I wept; but he hadn’t said anything. What a wonderful guy he could be at times.

When classes started up again I had developed a new routine; I now spent most of my free time in Debi’s dorm room. No one bothered me; the girls there simply looked on me with sympathy as I mourned. They didn’t knock on my door, they didn’t throw me out at night, I almost lived there. Once each day I would go back to my old room and do a quick clean up, washing mine and Trent’s laundry as always but I never stayed for long. Eventually I decided to unpack a few things at Debi’s, and put everything back where it belonged and also began wearing panties again; while folding them and putting them away the urge had simply became too much for me. I knew Debi would want me to have the clothes and Abby apparently didn’t want any of hers either. Finally, about the second week of January, I opened my present from Debi.

Breast forms. They were as realistic as could be with nipples and an adhesive to attach them to my chest. They were ‘B’ cup, the same as Debi. I cried again all night.

The next night I dressed completely for the first time since Debi’s death. It was sort of a celebration of Debi’s love for me. My new breast forms completed my look and I began to realize just how much I looked like a real woman when dressed. In honor of Debi I took out the magazines and her dildo and, with the help of a tube of lube she had, I slid it into my backside for the first time.

What can I say? Flashes of light burst in my brain after I got past the initial discomfort. Staring at that same cock picture and pretending it was Trent that was sliding in and out of my ‘pussy’ caused me to come as I never had before. I had been born with only one testicle and rarely did anything come out when I masturbated but that night must have been really special, because I left a large stain on the front of my blue silk panties. I lay there on Debi’s pink comforter and shook through two orgasms before taking the dildo back out for cleaning. I needed no more urging after that; I was hooked!

It was the very next day that my life changed again; at least it was for the better. The cheerleaders had gotten together and demanded that I be Debi’s replacement inside Lendy. Ms. Chlebowski wanted another female to wear it but all the cheerleaders were aware of how close me and Debi were, so they thought that it was fitting. Everyone knew that I had been the last person cut from the male side of the cheerleading tryouts, so I was obviously qualified. I was reluctant to accept, but the thought of a complete stranger wearing the costume was simply too much; and so I agreed.

The girl’s basketball team had a game in a few days, so I had to go to a couple of cheerleading practices and convince everyone that I had the routines down. No one was surprised that I did as they had all become accustomed to seeing me there watching Debi do them. One surprise I had was where I had to dress; in years past the person wearing Lendy had sometimes been a male and sometimes female, so there was a separate locker room just for whoever was wearing the costume. Debi hadn’t mentioned that. I was shown to the small room by one of the other cheerleaders and once I had shut the door found myself facing a large locker fronted by a wooden bench. Inside the locker was Lendy.

It was rough, I tell you. I shed yet a few more tears for my dear friend as I stared at the head of that fake puma. One of the custodians had cut the lock off for me so that I could get to the costume and when I finally managed to pull it out I was surprised to see what was hanging behind it.

It was Debi’s cheerleading uniform, given to her when she made the team as Lendy. She had never gotten to wear it but had kept it nonetheless. Perhaps she had worn it underneath the costume. Perhaps not. She had told me just how warm it could be in there. Hands shaking I removed it from the locker and hung it nearby. Further exploration of the locker allowed me to discover a small bag containing makeup and things for the shower. The locker room had a private one of those. A clean towel was discovered in a gym bag at the bottom along with a pair of white silk panties, a sports bra, a pair of white socks and some pink tennis shoes.

I put everything back except the costume but by the time that the next game rolled around, the thought of that cheerleading outfit simply would not leave my mind. Arriving well before game time I locked myself in my little closet and then stripped completely, utilizing the single shower to shave away the stubble of my body hair using Debi’s toiletries. I even used some of her perfume, figuring anyone that smelled it would think that it was simply clinging to Lendy from earlier uses. Afterwards I sat shivering on that cold wooden bench and stared at the outfit, wondering just how wonderful it would feel to wear it.

Debi had never brought it back to her dorm, so I had never gotten to try it on. I was certain that it would fit me; all of her clothing did, but wasn’t certain if I should or not. Finally I convinced myself that it would be ok to try it on, Debi wouldn’t mind, but there was no way that I could dare wear it out of the room; not even under the costume. Hurrying now so that I could try it on before having to change for the game, I slipped on the panties she had in her gym bag along with the bra. I had my breasts forms with me, a hint that my subconscious had already made the decision even if I didn’t realize it yet, and soon I was sliding that glorious garment onto my body. Grateful for the room’s mirror, I admired myself for a long time; my shaved legs looked fantastic beneath the short skirt and my breasts forms pushed out the top quite convincingly. With my hair back in my fantasy pony tail (it was short but doable) I looked and felt more feminine than ever before. My pleasure was almost orgasmic!

Telling myself that I would try on the costume over the outfit just to see how hot that it indeed was, I didn’t even hesitate once the head was in place but marched confidently out of the locker room towards the gym. No one would ever know what I was wearing beneath the costume and even if I took the head off during a break no one could see anything below my neck. It was perfect!

I sounded really brave but believe you me I was scared to death when I ran out with the other cheerleaders. I just knew that everyone in the stands knew what I was wearing beneath that fake puma fur. Somehow I managed to get through the game, I think we won but I’m not certain because of something that happened just before halftime that truly blew my mind. We were doing the ‘Lender’ cheer where the cheerleaders use their bodies to spell out the name of our college. The mascot was the last to run onto the floor and it was my job to be the ‘R’. It was while standing there being an ‘R’ that I happened to look towards the seat I had always sat in when cheering for Debi. Sitting in ‘my’ seat and smiling to melt a frigid heart was Trent.

What was he doing here? He had never been to a girl’s game before, I was certain. Not only was he sitting there he was waving at me! Flustered beyond belief I stumbled through the rest of the half and scampered to my dressing room as soon as the halftime show was done. This would be my only chance to take off the head and cool down; you weren’t allowed to take it off where any kids might see, even though there were no more than three hundred people in the stands and probably not more than a dozen kids in the whole gym. Just as I reached the hallway before my dressing room and reached up to pull the head off, I heard someone calling my name.

“Josh, wait up,” said Trent, trotting up behind me. “I’ve been yelling your name,” he said as he caught up, smiling at me in that way that I loved.

“Sorry, I guess I couldn’t hear you through the head,” I gushed, trying to understand why my beautiful roommate had followed me down here, or even came to the game for that matter. My heart was pounding as I looked up into his baby-blues. To him I might be a scrawny boy in a fur costume but at that moment I was imagining myself as a girl dressed in my cheerleading outfit. For me, that fur costume had ceased to exist. I was patently aware of every stitch of female clothing I was wearing and consciously pushed out my pert B cups as far as possible, wishing that they were real and that he would see me as I wanted to be.

“Yeah, I don’t hear too good when I’m getting head either,” he laughed. A typical Trent joke.

Trying to be witty and return his with a cute remark of my own I blurted, “I didn’t say when I’m getting head, I said I couldn’t hear when I was giving you head…”

I was shocked into silence for only a moment before trying to fix my error. Talk about your Freudian slips! “I meant when I was wearing the head… the costume head I mean,” I stammered, knowing that my face was brilliantly crimson.

Trent smiled all the more. “You’re not too good at those comebacks,” he laughed.

I smiled, grateful that he hadn’t teased me more than he had. “What brings you down here? I didn’t think you liked watching the girl’s games?” I asked after a short and uncomfortable silence. Uncomfortable for me, anyway.

“I don’t. Tall girls do nothing for me. I like ‘em short, about your height is perfect.”

Still blushing I filed that bit of information away for future fantasies. “I suppose you like them big breasted too? EE’s or bigger, right?”

Again that laugh. The sight of his lips were making me weak in the knees. How I would adore kissing them!

“Nah, not me,” Trent chuckled. “I like breasts, don’t get me wrong, but those big floppy ones? Nah. C cup is good, but give me a good old B cup anytime and I’m just fine.”

My heart almost leapt from my bra at that comment. If he only knew what he was doing to me! If he said one more thing like that I just knew I was going to cum in Debi’s panties.

“Actually I just came to see you, I mean watch you. Gotta support my roomie after all,” Trent said, blushing slightly for the first time since I’d met him. He suddenly leaned closer and sniffed. “You really smell nice.”

“Well…” I began, flabbergasted by his statement. “Thank you for that, Trent. I don’t know what to say.” I hoped I wasn’t going to cry again. Had I thanked him for coming to watch me or because he said that I smelled nice? I was so confused; thinking straight seemed to be impossible since I had mentioned giving him head.

“No problem, glad to be here, I’m really enjoying the show... well, guess I better get back out to my seat. Break a leg and do a cheer for me when you get back out there,” he said, turning away. I really didn’t want him to go. I wanted to drop that costume there on the hallway floor and shout ‘See? I’m a woman! Your woman, Trent’! Of course I didn’t. I watched him for a moment, his butt looks nice in jeans, and then turned with a sigh back to my locker room.

“Uh, Josh?” he asked, turning and coming back towards me. I gladly waited for him; every second spent talking to him while wearing what I was wearing was pure bliss for me.

“Yes Trent?” I asked, my voice as soft and feminine as possible. I knew he wouldn’t notice; my voice is not exactly masculine at the best of times.

“I just figured that I should tell you that… well the costume is kind of torn… I mean, there’s a rip in it, right here in the back,” he said, turning me and moving quickly before I could stop him.

My heart had stopped in fear. How bad was it? What had he seen? Before I could turn away or run for the safety of my dressing room he was behind me, lifting the puma’s tail in reaching in to place his hand directly on my butt cheek. His hand was beneath my skirt but the bottoms of my outfit barely covered my panties. He was touching me directly on the skin of my ass.

“It happened when you did the splits, there about halfway through the half? I believe I was the only one that noticed, you can’t see anything except when you do a handstand or cartwheel or whatever,” he said, slowing withdrawing his hand from my backside. “But maybe you shouldn’t do any more of those, if you don’t want anyone to see what you’re wearing,” he finished.

My heart had stopped again. I was torn between fear at being found out and desire for him to put his hand back where it had been. I stumbled out a thank you and nearly dived back into my dressing room.

I was mortified with having been found out, and by my roommate no less! My life was truly over, at least at this college. Even as I sobbed my heart out I was shedding my feminine clothing and wondering if my scholarship would transfer to another university. By the time I came back out for the second half it was nearly half-way over, one of the alternate cheerleaders had to be sent to get me and Ms. Chlebowski was furious with me. I mumbled something about having lost track of the time and she eventually forgave me. I was doing a better job than anyone else she could have gotten midway through the year since I knew all the routines already, so she really didn’t have any choice. I finally stumbled back onto the court wearing my boring old sweat suit; I had even removed my panties, beneath Lendy’s furry exterior.

Despite my change of clothing I was still wary about doing cartwheels in the costume. I wasn’t certain what all had been revealed but at the very least the hem of my cheerleading skirt had to been visible for Trent to have recognized it. I’m glad no one could see my face because the mixed embarrassment and fright must have been a horrible thing to see. Who else had noticed? Who else would be waiting to make fun of me after the game or tomorrow? Trent wouldn’t be in the stands anymore, I knew that, he’d be back at our room packing or tossing my things out the window. I didn’t blame him; seeing his roommate wearing women’s clothing must have been a terrible shock. Seeing him sitting there in my old seat was almost more than I could believe.

I’d never been so nervous and I can’t believe that it didn’t show. Everyone said that I did a great job in the second half but I don’t see how. Trent sat and smiled at me, applauding my every move without paying any real attention to the basketball game and my knees knocked in fear and excitement. Only once did he show anything but support for me, and that was just after my first flip of the half. I came up in the victorious, arms high position they teach you in gymnastics to find him frowning. Something had upset him, but what? Immediately after his smile returned as he applauded me and I soon pushed any thoughts of the frown away; apparently he wasn’t mad at me. That made me feel a little better; perhaps his moving out wouldn’t be quite so dramatic after all. By the end of the game I had resolved to be the one to move out just as soon as he brought the subject up; I could stay in Debi’s room after all; no one seemed to mind.

The game finally ended and I fled to the locker room. My intentions were to change as quickly as possible and hurry back to the dorm before anyone who had noticed what I was wearing in the first half could accost me. I even considered leaving in the costume just to save time but knew that Ms. Chlebowski wouldn’t like that. Maybe I could find a side door no one knew about, and so avoid the heckling crowds. An easy escape was not to be, however, as standing right in front of my dressing room door waiting for me was Trent.

My shoulders sagged at the coming confrontation. He was being polite about the issue, staying for the rest of the game was evidence of that, but there was no way I could avoid discussing what he had seen with him. Could I convince him to keep my secret as Debi had done? I doubted it. I just hoped he didn’t get really mad and beat me up.

“Hi Trent,” I mumbled, pulling the puma head off and clutching it to my side. “I hope you enjoyed the game.” My ‘hope’ sounded pretty weak and depressed. I just wanted the bad part of this conversation behind us. He smiled, even when depressed that sent a surge of pleasure through my body. He was so pretty!

“I didn’t really watch much of the game, I was just here to see you,” he said, placing a hand on my shoulder.

“Oh, well thanks,” I murmured, unsure how to progress from here. Surely he just wanted to tell me to get out of our room but he sure was beating around the bush about it. I decided not to be the one to bring up the subject. “I guess I did ok, I was pretty nervous.”

“You did a fantastic job! As good as Debi could have,” he bragged, bringing another blush to my face. There wasn’t anything he could have said about my Lendy skills that would have made me feel better than that. But, he wasn’t done speaking. “Of course, I thought you did a better job in the first half than you did the second.”

Here it came; somehow he was going to swing the conversation back around to what I had been wearing. Suddenly I decided that we needed to get out of the hallway for this conversation; being alone in my locker room with him might get me beat up but at least there was less chance for someone to overhear. Ducking around him I motioned for him to follow me into the room as I responded.

“I guess I was a little tired by the second half,” I said, thinking to myself that ‘tired’ should have been replaced with ‘mortified’.

“Tired? Nah, I don’t think it was that. You just seemed more… comfortable, in the first half,” he said as if thinking hard about it. “You’re movements were more confident; freer, in some way.”

We were halfway through the door now when I realized my mistake. My cheerleading outfit was scattered all over the place; I hadn’t even bothered to hang it up when I had changed. I had been in too big a hurry. Everything I had been wearing was immediately visible to Trent, and it was too late to distract him from following me into the room. Now he would know that I had not only been wearing a cheerleading outfit, but all the feminine underwear that went with it. Even my breast forms were visible! I could have died, and even wished that I could at that moment.

He said nothing, just stepping around me where I stood stiff-backed and closed the door behind him. I could see that he was looking at the panties I had been wearing; they were laying inside-out across the end of the bench. Next he stepped over to the locker itself and picked up one of my breast forms from the top shelf. Cupping it in his hand for a moment he smiled and said: “B cup, I believe.”

That was all I could take, I collapsed onto the bench and began to sob. As much as I had cried since Debi died I wouldn’t have thought that any more tears were possible but they flowed freely anyway. Surprise couldn’t begin to express my feelings when Trent sat down beside me and put his arm around my shoulders.

“Shh, Josh ease up man,” he said, hugging me to him with one arm. I wasn’t sure how to react so I simply sat very still, the tears flowing but the feeling of his arm around me too wonderful to ignore. I tried to think of some excuse for what I had been wearing; a lost bet, a hazing ritual for a fraternity, but nothing that I sputtered made sense. Trent wasn’t listening to my babbling anyway.

“Look Josh, you like wearing women’s clothing, that’s ok,” he said, shushing me. “If it makes you happy, then I’m ok with it. I’m sorry if my finding out hurt you but you have to believe me when I say that your secret is safe with me.”

I tried to choke back my sobs but it was difficult. Of course my secret was safe with him. Now that I thought about it; he couldn’t tell anyone for fear of looking gay himself after having lived with me for all those months. His soft voice eased my tension some, and the stiffness left my body allowing him to pull me a little closer by my shoulders. I couldn’t think of anything to say so I just sat silently, miserable and yet elated at the feel of him sitting so close, even through a puma costume his body heat was palpable.

“It’s not like I didn’t suspect; a lot of people around campus think that you’re gay, but I didn’t realize that you wanted to dress up in women’s clothing. I think that’s great; you should do it if that’s what you feel,” he said, squeezing me closer again. He may have been doing that to show support but he was seriously turning me on!

“Just because I wore women’s clothing, it doesn’t mean that I’m gay!” I managed, looking towards him but not able to lift my gaze above his chin. I was afraid that he would see the lie in my eyes immediately.

“I understand that,” Trent said, reaching down and cupping my chin gently. Lifting it up, he forced our gazes to meet before he continued. “But you are gay, aren’t you Josh?”

The tears were welling up again and I tried to choke out an argument but all that came from my mouth was a sob and four whispered words.

“My name is Jill.”

I cried really hard then. He took me in both his arms and held me close, making those small ‘shh-ing’ sounds that people do to calm someone who is crying. I put my arms around his waist and buried my face in his chest. I was miserable but loving it too. I even cried a little longer than necessary just so he wouldn’t let go. Finally my sobs eased and he pulled away. Reluctantly I let him go before turning to the locker to find a cleanex. It was a good thing that I wasn’t wearing makeup; it would have run all down my face.

Woodenly I began to strip off Lendy, my gray sweat suit plastered with moisture and a distinct odor of sweaty body rising up from me. I stripped the top off but stopped before removing the bottoms; I didn’t want Trent seeing me naked or even nearly so. I needed to take a shower badly but couldn’t so long as he was here. I sat with my back to him, suddenly noticing the two red splotches on my chest where I had removed the breast forms too quickly, looking only at my feet. He stood behind the bench watching me, expecting me to say something, I suppose, but I had nothing to say. My life was over; despite his claims I knew that the whole campus would soon know everything about me. At that moment I really wished that I could die; perhaps Debi and I could be together again.

“I never really noticed how attractive you are,” Trent said, his voice soft yet causing me to jump when he spoke. “I bet you’re beautiful when you’re all dressed up.”

I said nothing; my heart was pounding too loud and would have drowned me out anyway. I wanted him to say that again but he didn’t; he moved on to something even more wonderful.

“As a matter of fact, I bet you look really nice in your cheerleading outfit. I’d really like to see you in it, without the Lendy suit over the top,” he chuckled.

Somehow I managed to turn my head enough to see him. I wanted to see the derision on his face; the proof that what he had just said was nothing more than a cruel joke. I saw nothing like that; only sincerity and his to-die-for smile.

My words were almost a whisper. “I… can’t wear it home… someone would see…”

“No problem,” he said excitedly. “Just bring it home with you and you can model it for me... Jill.”

The woman inside of me leapt for joy at Trent saying my feminine name. The tears in my eyes turned instantly from sorrow to happiness and it was all that I could do not to jump up from that bench and into his arms. At first I had no idea how to respond but finally something came to mind.

“If you want me to, I will Trent,” I managed. “But I’ll need some time before you get there… I don’t want you to see me change.”

Trent’s smile went from hot to panty-melting luscious. “No problem, I’ll go grab a burger and see you at our place in, what? An hour?”

I nodded happily as my mind replayed his words; ‘Our Place’.

He left, suddenly seeming as awkward as I ever was around someone I wanted to date. Our goodbyes were perfunctory but I barely noticed, waiting for him to close the door so I could jump into the shower.

I showered quickly, re-shaving my body despite having done it only a couple of hours before. I needed to look my best after all. Once I was clean and at least partially toweled dry I hastily put on a pair of panties, and to my surprise, a clean bra for the walk home. I rarely wore a bra outside but somehow this situation demanded it. There was still a chance that Trent was setting me up somehow, perhaps bringing some of his jock friends over to embarrass me once I was dressed, but at that moment, for the first time in my life, I just didn’t care. If there was even the slightest chance that I could become Trent’s girl then I was going to go for it. Once my drab male outer clothes were in place I hastily repacked all my girly things and with the cheerleading outfit safely stowed in my gym bag, rushed out of the building.

Almost running I hurried home, stopping by Debi’s place for a few things I would need along the way. I reached our room with only thirty minutes to prepare and flew through my routine. I know it was silly but I put on a pair of sheer pantyhose along with a matching white panty-bra set that was very lacey and almost brand new. The cheerleading outfit slid on as dreamily as before and the little bottoms fit as snugly as they could have on Debi. A pair of ankle socks with fuzzy little pink balls and Debi’s pink shoes completed my outfit, giving me only fifteen minutes to fix my hair and put on my makeup. I made it but only barely; Trent arrived exactly on time; not a second late!

It surprised me that he knocked; he lived there too, after all, but I was glad that he did as it gave me a moment to calm myself. My hair was back in its ponytail, I really didn’t know what else to do with it, and at least according to the mirror I looked as good as any real cheerleader could have. Practicing my girlish walk, just as Debi had taught me, I minced my way to the door as I struggled to breathe through my anxiety. Thankfully the door had a peephole, so being able to see that Trent was alone helped calm me somewhat. Finally throwing caution to the wind I threw the door back and gave him his first look at Jill.

Was he surprised at how good I looked? He says that he wasn’t but I could tell that he was flabbergasted. He had brought me flowers (where had he found them this late?) and never failed to call me Jill after he entered the room. We talked for an hour, me sitting demurely on the edge of a chair while he sat half-reclining on his bed. Eventually he convinced me to put on a cheerleading exhibition for him and watched excitedly as I kicked my legs and tumbled about the room. I could tell that he really liked my legs and when I did a hand-stand he held his breath the whole time my skirt was up; the crotch of my tiny cheerleader shorts completely exposed to his gaze. Finally, out of breath, I allowed him to grab my hand and pull me down to sit next to him on the bed. I looked at him, smiling with the joy of showing off for him and found his lips closing in on mine.

We kissed.

It wasn’t a mouth-open tongue-wrestling match, it was just a kiss even if the world did stop rotating. Our mouths were slightly open, I know I didn’t breathe the whole time, and we probably only held it for about ten seconds but I was immediately in love with that sweet man. When we broke away we didn’t look at one another for a minute or so; just sat looking away and thinking about that kiss. My whole body was tingling; from my toes upward, at the thought of what had just happened. My mind was spinning; perhaps from a lack of oxygen but the kiss had contributed as well. I wasn’t sure if he was sorry we had kissed, but if he wasn’t going to say anything to ruin the moment I certainly wasn’t. Finally I felt him turn towards me so I looked his way as well; even if he was going to tell me that kissing me was a complete mistake I wanted to watch his sweet lips as he said it. He had kissed me!

Whatever he had been planning on saying was never spoken; we silently drifted back together for another soft kiss. Another followed that one and soon enough we were going at it hot and heavy; our tongues licking one another as our lips moved softly together. We didn’t break our lip-lock for what seemed like only a few minutes but could have been hours. When I came back to myself Trent was lying back on his bed and I was laying half-way on top of him. His arms were wrapped tightly around me and my hands were wandering across his muscular chest. We stopped for a moment to catch our breaths and I took the opportunity to rest my head on him as well; it felt as wonderful as I had ever imagined to be lying there in his arms. Soon though I knew it would go further; there was no way I was going to let this end here.

Trent excused himself to go to the bathroom and I freshened up a little as well. When he returned I met him at the door and after making sure the hallway was clear, gave him a long, lingering kiss. His hands slid up my skirt and found only panties between his skin and my rear. I think he liked that; he certainly gave my ass plenty of attention. Once the door was closed I took his hand and led him back to his bed, mine didn’t even exist at that point; I had wanted to be in his with him for so long. I helped him undress as we went; getting those tight jeans off was a chore but I loved ever second of it. Finally came the moment I was waiting for; the removal of his underwear. Trent wore briefs most of the time, and tonight was no exception. I dropped to my knees when his ‘tighty-whities’ were all that he had on and smiled shyly up at him as I grabbed onto the waistband.

He smiled back, and I excitedly began to slowly strip him of his shorts. I was desperate to see his cock but didn’t want this wonderful moment to end too quickly. Slowly, so slowly, I pulled down on the elastic, watching for the first sign of his manhood to appear. I had no preconceptions of how large or small he would be; I knew that he had to be bigger than me, and I really had no idea what it would look like, my only experience with a ‘live’ cock was with my own, and that had never caused the sort of bulge I had seen in Trent’s shorts. I kept expecting to see the head of his cock first, surely that bulge meant that he was already erect, but as the underwear descended I continued to be frustrated. Where was it?

Suddenly it was there, but not the engorged cock head I had been expecting but the thick base of a truly man-sized dick emerged from the crop of kinky pubic hair. I couldn’t believe how thick it was, or that it was apparently still not hard despite the bulge, and began to pull his shorts down even more slowly as my hungry eyes devoured each emerging inch. How big could it be? I couldn’t begin to guess but my mouth was already watering over what I had seen so far.

Inch after glorious inch was revealed as I pulled the shorts down. It was partially erect but protruded at least two inches straight out from his body before it sagged downward beneath its own weight. He gave a sigh of relief as it was freed; I guess it was pretty uncomfortable all bent up like that. Finally, just as I decided that it might drag the floor before I freed it, a complete exaggeration of course, the head of his cock slid free of the restraining elastic, and I could finally behold the beauty that was his dick.

Did I mention that it was big? It was, wondrously so. I don’t know how long exactly but it was certainly bigger than anything I had ever seen on the internet. The head itself was thick and looked to be longer than my thumb. It was the most beautiful thing I had ever seen, at least until it was completely hard. I realized that I was holding my breath and let it out quickly; it was so beautiful it was breathtaking anyway; no sense in passing out now before I had even gotten to touch it!

Hands shaking, I reached out to grip Trent’s massive member, smiling at his groan of approval as the thick base was gently gripped in my palm. I still couldn’t take my eyes off it; it was so perfect with its thick ropey veins and fantastic proportions. It immediately began to twitch once I had it, and to my amazed sight began to thicken and grow. The head started lifting with each twitch, rising from its downward-pointing position until it was almost sticking straight out in front of him… and right directly at me. Tentatively I leaned forward and licked it right on the very tip, reveling in the salty taste of his cock. It was delicious! Opening my lips I kissed it next, sneaking in a second lick as I did so and then grabbed it with my other hand as well so that I could better admire the lipstick I had left there.

“Oh, yeah, Jill,” Trent groaned, his thick cock now jutting proudly out before him. I couldn’t see how it could get any bigger but it was obviously still getting harder and I adjusted my grip to compensate. Trembling with pleasure I opened my mouth even wider and slid his glorious manhood inside, carefully pulling my teeth back just as Debi had taught me and allowing it to nestle on my tongue. Nursing gently on it for a moment with just the head inside gave me a good taste of his precum as his mammoth dick hardened even further inside my mouth. I absolutely adored the flavor. I pulled back only for a moment, his groan of disappointment was too sexy to ignore, and finally got to see him fully erect; and believe you me it was magnificent. I slid him back where he belonged and slid it in and out of my mouth for a while; so happy I could have died.

Rising to my feet I kept his cock firmly in my hand and gently led him to his bed, turning him and pushing him so that he lay on his back before me. He was all mine; his cock jutting firmly upwards with its need; a need that only I could fulfill. Sighing in pleasure I knelt beside his bed and with his cock still gripped in one hand, lowered my face upon it.

It was wonderful! I kissed, licked and gnawed at his beautiful beast, trying to taste every glorious inch. I couldn’t deep throat him, unfortunately, but I did the best that I could. I quickly found the spots he liked me to lick the best and all too soon I sensed that he was nearing the point of no return. I wanted it to last longer, honestly I did, but I just couldn’t wait to taste his cum so I left off sucking his balls and positioned myself so that my hungry mouth was right above him and then I slid his wonderful cock back into my mouth and began bobbing up and down; all the while stroking his meat with both hands as I urged him to cum in my mouth. With a grunt and an ‘Oh, Jill!’ he did just that; arching his back as his sperm erupted into my waiting mouth.

All that I can say as that it was even better than I had ever imagined. Had he cum a gallon, I would have wanted to taste every drop. As it was I ended up wearing a lot of it, but enough made it onto my tongue that I was satisfied for the time being. I sucked on it long after his orgasm was complete, and he rewarded me by never going even a little bit soft.

“Can I fuck you, Jill?” he eventually asked once his breathing had eased. I said nothing, just used my favorite handle, his cock, and urged him out of the bed so that I could take his place. My ‘pussy’ was already well lubricated so I lay on my back with my legs spread wide; I couldn’t wait to feel however much of his cock I could take inside me. He didn’t make me wait but immediately crawled on top of me after flipping my skirt up. Once his body weight was in place, that was really nice all by itself, I felt him tugging my panties to one side and then, glory of glories, his cock head pushing up against my opening. I shivered in a mixed state of bliss; combining fear, anticipation, and a life of desire into one overwhelming emotion. Trent moved his mouth to my neck where he bit lightly at me as my attention remained only on that part of his body that was entering mine. Then, after giving me a moment to gather myself, he began to thrust his hips forward.

Yes it hurt; it felt amazingly wonderful as well. I couldn’t take all of himl but I did pretty well for a virgin. Trent was inside me, his big cock pounding my little pussy as he drove me to orgasm after orgasm. Debi had tried to tell me how good it felt to have a man inside you but she just couldn’t do justice to the act itself. My mind ran away on the waves of repeated orgasms, reveling in the feeling of him sliding in and out of me. Later I heard some of our neighbors congratulating Trent on the fucking he gave that ‘slut’ that night, so I know that I wasn’t too quiet. I didn’t care; all I cared about was the pleasure I was getting from my man. Ten minutes or six hours later, I couldn’t be sure; I felt the warm spray of his sperm inside me. We clung together for a while, whispering little endearments until we fell asleep in one another’s arms.

We tried to keep our relationship a secret and we were successful there; however my crossdressing quickly became the best-kept secret that everyone at Lender College knew about. One of the cheerleaders had also noticed what I was wearing underneath Lendy that first game but didn’t say anything for a few weeks. She apparently had a brother who crossdressed and so was sympathetic. Eventually she did tell her best friend and the two of them decided to speak with me about it. Before long the entire cheerleading squad knew about me and ultimately I was allowed to practice with them in Debi’s cheerleading outfit without Lendy. This led to my forsaking my men’s clothing completely; everyone knew about me already and wearing skirts to class was thrilling. Before I began living as a woman I would never have dreamed that revealing my feminine side could have filled me with such confidence but it most certainly did. Being caught wearing panties and a bra was once my greatest fear but now being seen in public as a woman is something I look forward to.

When one of the girls from the squad twisted an ankle, I was allowed to fill in as an alternate on the cheer squad. That only allowed me to sit on the sidelines and shake my pompoms but it was still a wonderful experience. There were a few nasty things said to me here and there but with Trent’s love and the support of my new friends I overcame them; being a woman full-time was simply too fantastic to worry about that sort of stuff.

Naturally my relationship with Trent became more difficult when my secret got out. He didn’t want to be thought of as gay and maintained that I was all woman to him. I was thrilled with that thought and so I offered to move out of our room and into Debi’s to help preserve his reputation. That was what I did but I still spent most nights with Trent; I still cleaned his room and I did all of our laundry together. I also took care of his more basic needs; that man’s sex drive is insatiable! I am so thankful for that. No one said a word to me about staying in Debi’s room, I didn’t think that they would, and the other girls of the dorm welcomed me as their new sister. I was even offered to pledge with a sorority for my sophomore year!

The next year flew by and so many wonderful things happened to me. Trent and I are still together and as my transformation to living as a woman full-time began we decided that we should move away from Lender College. When that year ended I was beginning hormone treatments, how I desperately wanted my own breasts, and Trent accepted a scholarship at a larger university. I was able to transfer to the same school myself; apparently the grades I make are universally accepted. By the time the new school year began my name was officially Jill and so far as I knew no one at the new university had any idea that I was once Josh. That took some creative paperwork but I managed it. My computer skills are topnotch. We live in a small apartment just off campus and some of our new friends think that we’re married… I love that thought. I wished now that I had legally changed my last name when I became Jill.

I eventually told my mom about Trent, and she wasn’t as supportive as I had hoped but we’ll work through it. I walked on to the cheerleading squad at the new university and made the team… as an alternate (argh!). Still, I get to practice with them and despite my love for Trent do enjoy having my little body tossed around by those big strong men. Sitting upon their hands while they lift me up in the air is pretty nice too; nothing like a good grope to make a girl feel special, lol!

My breasts finally began to come in by the time my junior year began; I was getting so tired of wearing those breast forms. My doctor says that I seem to be destined for ‘big B’ or borderline C cup. That’s more than enough for me, and for my Trent. He loves my breasts and spends a lot of time kissing and sucking them. What that man can do with a nipple… wow.

I think this is going to be our year. After starring at Lender as a freshman, Trent didn’t have to sit out a year but still didn’t play a lot as a sophomore. Now, as a junior, he is starting and is one of his team’s better players. I think I can make the cheerleading squad for real this year; not just as an alternate sitting around waiting for an injury, and if not the dance squad is trying hard to recruit me! I’ve been to meet Trent’s family lots of times; they have all accepted me as a female and I’m not sure if or when we’re going to tell them the truth. Lately I’ve been considering surgery to finish the deal and if that happens, maybe I won’t have to. It would be nice to have my very own vagina but I’m not sure that I have enough ‘equipment’ for the doctors to work with down there.

Thank you for listening to my story. I am happier now than I have ever been but am more than a little sad that it all came about because of the tragedy of another. I wish Debi could be with me and share in my joy but I will always love her for what she gave me; a whole new life.