This is a true story of how my Mom feminized me as a teenager. She had caught me wearing her pantyhose the summer before seventh grade. I got the surprise of my life the first Sunday of junior high, when she started encouraging me to wear them, and then it was all downhill from there. After a few days at my sister-in-law’s, she decided to turn things up a few notches -- Tracy

It was an incredible month. We had sex almost every day. After that first bout with constipation, I didn’t have any more problems. Every morning after breakfast, Char and I would go in the bathroom together and have what Char always called ‘our morning sit on the pot’. We would go in wearing just our pantyhose and bathrobes. One of us would sit on the toilet and have her bowel movement while the other made small talk and did her makeup at the sink, and then we’d switch places. Then we’d go back to our rooms and get dressed.

After work we were always really touchy-feely. When we would get home the first thing we did when we got inside the door was kick off our heels and parade around in our hosed feet the rest of the night. Every time we’d get near each other while making dinner and cleaning up afterward, we’d run our fingertips over each other’s bottoms and giggle.

After dinner we’d cuddle up on the couch and watch TV for a while. We’d nuzzle together and kiss until my dick got so hard I’d reach in my hose and straighten it out, then we’d race upstairs to the bedroom and tear our clothes off and fuck like mad. On Sunday nights we took a shower together and Naired our legs for the upcoming work week, and then shaved our armpits.

One morning at breakfast, she said, “Let’s wear slacks today instead of skirts. I think I’ve got some dress slacks that are a little too small for me, and they should be perfect for you.”

After we did our BMs, we went in her room. She opened her closet digging around in the back, and handed me a pair of beige slacks on a hanger. “Here, try these on,” she said. “Remember they’re women’s, so they zip up in the back.”

I stepped into them, and they slid so softly up my nyloned legs. I pulled them up to my waist, and had to work at getting them zipped in the back – I wasn’t used to doing that! They were pretty long, but Char said, “Don’t worry about the length, you’ll wear heels with them. Go put on those high heel beige sandals you’ve been wearing.”

I sat down on the bed and put them on, and stood back up. The hem was now about an inch above the floor, and you could just see my pantyhosed toes sticking out. “Perfect!” she said. “Now we’ll pair that with my lacy beige top.”

“Mmmm,” I said, after I slid on the top. “I feel so smooth and sleek. It’s just like I felt when I wore the Young Organist’s outfit.”

One day she dressed me up in a cami and tap pants instead of a slip, in a green double-breasted suit dress and beige pumps. It was a very conservative look, unless you knew what I had on underneath.

We were talking to one of her co-workers, Beth, and Char said, “You should see what Brie has on underneath that dress. She’s wearing my powder blue daywear.” She looked at me and said, “Everyone else has left for the day. Go in the bathroom and take off the dress and model the cami and tap pants for us.”

I froze in fear, but then Beth touched me on the shoulder and said, “It’s OK. We’re not going to embarrass you. We want to see how pretty you are.”

I went in the bathroom and took off the dress, and made sure my dick was tucked firmly in my hose. I walked sensually out of the bathroom and stuck a pose against the edge of the door in my high heels.

“Wow,” said Beth when she saw me. “Look at her legs.”

I turned and looked at my profile in the bathroom mirror, and I almost passed out. My shaved legs were perfectly smooth in the sheer-to-waist hose, and the high heels really accentuated my calves. The lacy hem on the tap pants barely covered my rear end, and you could see my long legs all the way from my buttocks all the way down to my toe cleavage in the pumps. I was so sexy! My dick immediately started to get hard, and I hoped Beth didn’t notice it through the tap pants, which were thankfully loose.

After a few minutes, I went back in the bathroom and put the dress back on. As we left the office and got in the car, I said, “Oh God Char, I can’t believe how sexy I looked standing there in front of you and Beth. I was so hard. I hope she didn’t see my dick. God, I want to fuck you so bad.”

When we got home I went in my room and took the dress off and hung it up, and then came out of my room in the cami and tap pants and high heels. I walked out into the kitchen where Char was starting to fix dinner, my high heels clicking on tile floor. Char looked at me and I puckered my lips and made a kissing noise. She went into her room and took off her blouse and skirt, and came back out wearing just her slip and hose and heels. She made the same kissing noise back at me, and we ran into each other’s arms, French kissing. We ran down the hall to her bedroom and fell onto her bed. Pausing just long enough to pull down our pantyhose, we fucked hard and fast, both coming within what seemed like seconds.

Later that night, we were looking at clothes in Char’s closet, deciding what we were going to wear the next day. Char was sliding hangers full of clothes back and forth when she stopped suddenly and said, “Here! This is what you should wear tomorrow!” and pulled out a multicolored blue long sweater.
“This is really long on me, and you could wear it as a dress! Remember that time you were here a couple of years ago and I had you put on my navy blue pantyhose and platform sandals? You could wear those with this! It would be so cute!”

She sent me to bed with the dress, the platforms, and a pair of navy blue sheer to waist pantyhose.

The next morning I put on the navy blue pantyhose before I went out in the kitchen for breakfast. When I went in the bathroom to tinkle, I noticed that there was a box of tampons open on the bathroom counter. Char and I had been making love for several weeks, and it occurred to me that it was probably her time of the month.

After breakfast, we went in the bathroom and had our morning sit on the pot. Char went first, and she was on the toilet for a long time. I snuck some glances over at her and her face was red and she was pushing on her stomach, but after she wiped and stood up, there wasn’t anything in the toilet. “Mmmm,” she grunted, “I guess I’m not going to be able to do anything. That’s another way you know your time of the month is coming. Most of us get constipated when it’s due to start. Being constipated makes your period cramps worse, so you want to stay on top of it before you get too plugged up. Bad news, sweetie. No more sex for a few days till it’s over. You may have to. . .” she paused, “stimulate yourself down there if you want to get off, since I can’t do it right now.” We petted and kissed, and then she pulled back. “I know what we can do! Since you’ve pretty much had the whole woman experience the last few weeks, how would you like to see what it feels like to have your time of the month? I mean, you couldn’t experience the whole thing, but you could see what it’s like to sit on a pad for a week, and have a tampon up in you.”

The thought was making me hard. “Oh, Char,” I said, “I’d love to try anything that makes me feel like you.”

“Alright then, after you do your push job we’ll put one up in you.” I sat down on the toilet and moved my bowels while Char opened the box of tampons and took one out. She tore the paper wrapper off and showed it to me. “Since you don’t have any lubrication down there, we’ll have to put some lube on it so it will go in more easily.” She opened the tube of K-Y and put some on the tip and the cardboard tube. After I wiped and flushed, she said, “Now stand up and put your right foot up on the toilet to help open up your bottom. Take some deep breaths and relax.”

She pressed the tip of the tampon to my anus, and said, “Tell me when you’re ready.”

I took a deep breath. “Okay,” I said, bearing down to relax my anus. She pushed the tampon up in me, and said, “You want to put it in about this far. Then, hold the outer tube in place with one hand, and push the inner tube through it to insert the tampon, like this, with your other hand,” as pushed it up in me, then withdrew the applicator. I couldn’t believe how sensual it felt having it up in me.

“Well, how does it feel?” she asked, staring at my dick fully hard and standing at attention, and she said,

“I take it you like it!”

“Mmmm-hmmm,” I said, afraid to touch myself for fear I’d come.

“Even with a tampon, you still need to wear a pad in case you leak. If you’re wearing pantyhose and they don’t have a cotton crotch, you’ll have to wear panties under your hose. Since our hose have one, you can stick the pad to your nylons. Like this,” she said, peeling the tape off the adhesive strips and sticking it into the crotch of my pantyhose.

“Now pull them back up, and make sure the pad is firmly against you,” she said, and I pulled the pantyhose up firmly and pushed the pad into my crotch with my fingers.

“How does it feel?” she asked.

“Bulky,” I said, “after going without underwear for a couple of weeks.”

“Welcome to the club,” she said. “Having your period is a constant exercise in hiding the feminine hygiene products to absorb it. You need to change your tampon every twelve hours, or sooner if it starts to leak. Yours won’t, of course, but change it twice a day. Don’t flush it. Wrap it up in a Kleenex and put it in the wastebasket.”

We went back in our rooms to get dressed. When I finished dressing and looked at myself in the mirror, I couldn’t believe how sexy I looked in the outfit. When Char saw it, she said, “Wow! You look so sexy in that! You’re going to have to be really careful to keep yourself covered up.”

That was for sure. I started walking with my hands at my sides and pulled the hem of the skirt down every time I moved. As we were getting ready to leave, Char came out of the bathroom with more tampons and the tube of K-Y. “Here,” she said, “put these in your purse. You should always have a tampon with you, since you never know exactly when your period is going to start. You’ll need the K-Y too to lube them up to go up in you. The lube is also nice to have when you’re having a big difficult BM that won’t come out. Put some lube on your finger and put it up in your rectum and it’ll help it slide through your boy pussy.”

That evening, after we cleaned up the dinner dishes and sat down on the couch to relax, I snuggled up to Char like I always did before we started petting. Char put her arm around me and said, “So how do you like wearing feminine protection?”

“Mmmm, it’s different. I could feel the tampon in my bottom every time I moved, and it really turns me on. I’m so hot right now, I wish we could fuck.”

We moved into each other’s arms and kissed deeply. “Mmmm, me too sweetie, believe me. It sounds like you like having long thick things up your bottom.” We snuggled for a little bit, and then she said, “I know what we could do. A lot of couples have sex in the woman’s bottom when she’s having her period and she’s constipated. It helps her have a BM. Would you like to try anal?”

“Mmmm, sure,” I said. We walked back to the bedroom arm-in-arm, and I got so hard again, feeling the tampon in my rectum and my pantyhosed feet sliding on the hardwood floor. We took off our dresses and slips, laid down together on the bed, and started petting. After a few deep kisses, I couldn’t stand it anymore. I had to pull down my panty hose and release my erection. She sat up and said, “Show me your tampon string,” giggling. I rolled over on my back and spread my buttocks with my hands. She played with the string, and tugged on it slightly. “Oh God, that is SO hot. A pretty teenage boy wearing pantyhose and a tampon. Our janeboy is having her period.”

“You really have to get lubed up well for anal,” she continued. She got the K-Y out of the bedside table and pulled down her pantyhose. She got up on her knees and turned away from me, then bent forward and spread her legs, treating me to a full view of her beautiful bottom. I could see the tampon string hanging down out of her. She opened the K-Y and put a big gob on her middle finger, and then rubbed it around her perfect little anus. She put some more on her finger and inserted her finger into her anus, sliding it in and out, moaning as she did so. I was ready to explode. She turned to me and put some K-Y on the head of my erection. She said, “God, I can’t believe how hard you get for a fifteen year old boy.”
I said, “When I have hose on, I’m always this hard.”

She said, “Are you ready?”

“Mmmm-hmmm,” I moaned, eagerly.

She laid down, rolled over onto her left side, and said, “Snuggle up to my back and get comfortable. Lay your dick in my crack.” I snuggled up to her back and buried my nose in the nape of her neck, smelling her sexy perfume as our bodies fit together perfectly. After a moment, she said, “Now guide your dick up to my rectum.”

I put my hand down between our warm bodies and spread her crack with my hard dick. I tentatively pushed a little, and she wiggled around until I felt my glans engage her anus. “Now enter me gently,” she said.

I pushed gently, not wanting to go too fast and hurt her. It didn’t feel like I was getting anywhere until she took a breath and pushed gently, and her anus relaxed and I slipped in. Oh God, it felt so good. She settled back against me and I started to thrust gently. It was so sensual. We felt so close, spooned together and our pantyhosed legs rubbing on each other. I could still feel the tampon in my rectum and thought she must feel the same with my dick in her bottom. She farted several times around my dick, and she said, “Sorry. I think my bowels are finally starting to move a little.”

My orgasm came on so fast I didn’t realize it was coming. My semen exploded into her, and we both gasped in pleasure. I felt her stool touching my glans, and I slipped out. “Oh, I’ve really got to go poop,” she said, running into the bathroom and sitting down on the toilet. I heard her grunt and then heard a big stool splash into the toilet, and she moaned in relief. She rolled off some toilet paper and wiped herself, and then flushed. She came back in the bedroom with a soapy washcloth, sat down next to me and wiped off my dick. As always, her touch was heavenly. She stretched out next to me and we cuddled for a little while, and then she said, “Want to go back down and watch TV?”

“Sure,” I said. We got up and put on our bathrobes, then went downstairs to the family room and turned on the TV. We snuggled together on the couch, our pantyhosed legs intertwined and our heads on each other’s shoulders.

The next two mornings Char had a normal BM, but the day after that she wasn’t able to go. That afternoon, she was getting crampy and gassy. After dinner that night, she said, “I really need it in my bottom again. I feel so bloated.”

We walked hand in hand back to her bedroom and disrobed. This time we already knew what to do, and it felt so natural. After I ejaculated and pulled out, she said, “Come on in the bathroom with me so I can go.”

We went in the bathroom and she settled on the toilet. I could hear the crackling sounds as she passed her stool. She had a good satisfying bowel movement, and it was easily evacuated. She moaned in pleasure this time, instead of frustration. After she wiped and pulled up her hose, she touched my hair and said, “I think I really need to keep you around.” We both giggled.

We went back downstairs to watch TV. She took off her bathrobe and spread it out on the couch. “Take off your robe,” she said, and I wondered what she had in mind. We sat down on her robe and snuggled together, and she pulled my robe on top of us. Feeling our perfumed bodies snuggled together through the nylon and lace was just heavenly!

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The following week, it was time to go home. That morning, as we were having breakfast, she said, “I have just the outfit for you to wear home. Let’s wear slacks so we don’t have to ride in skirts. Wear the beige lace top with the back-zip slacks and sandals.”

We went in her room and she handed me the outfit. I wondered about what I was going to have to change back into guy clothes. “Um, Char?” I began. “Where will I be able to change back when we meet Mom?”

She came over and stroked my hair. “You won’t have to. You can wear these home. This is my gift to you. This will give you a slacks outfit you can wear out at home. I know you love these beige sandals so I’m giving them to you. I’ll get another pair.”

The ride home was bittersweet. I so hated to go back to guy clothes! When we got to Windsor and met Mom, she did a double take when we got out of the car. “I can’t believe my eyes!” she said. “You two look like sisters!”

We went into a nearby restaurant for lunch. As we sat there, I noticed Mom kept staring at me. Looking at my chest, she said, “You’re even wearing a bra!”

Char looked over her menu, and said quietly, “She’s been wearing a bra ever since she got here! How else would she have a figure?”

“Of course,” Mom giggled.

After we got on the road, I noticed Mom kept staring at me. “I can’t get over how pretty and feminine you look. When I first saw you get out of the car I didn’t even recognize you. Char really worked her magic on you!”

“I know,” I blushed. “I’ve been a girl for a whole month. We wore dresses or skirts and heels every day. It’ll feel weird to go back to dressing like a guy.”

Mom said, “So tell me all about it!”

I did, telling her some of the outfits I wore, and the things we did. Of course I skipped the part about having sex nearly every day. “We always wore skirts or dresses during the week to work. On the weekends we were girl tops and shorts and sandals. She got me this pair of girl’s jeans that were so tight I had to wear pantyhose under them just to get them to slide up all the way. Sometimes when we went out at night we wore our tight jeans and high heels. I was in girl clothes the whole time I was there!”

The next morning, Mom asked me how it felt to be a guy again. I said, “It feels weird to not have a bra and pantyhose on after wearing them almost every day for a whole month! Just like on Sundays, the first thing I did when I got up in the morning was put on pantyhose!”

Mom laughed. “I can still see bra marks on your back. They’re fading, though. Well you can still wear them if you want, you know.”

The next day I decided to be a girl again. I put on a bra and pantyhose with the girl jeans shorts and blue and white top that Char had bought me, and Mom’s high heeled white sandals. It felt so natural to be back in hose and high heels again!