A Deep Dive into the Back of the Closet --
by Anonymous
"Hmmm, so this woman you saw. Was she attractive?" Jennifer, my therapist, said.
"Oh yeah, she was about 5'8", 140 lbs. Long dark hair in a ponytail. Blue eyes. She was wearing this white short-sleeved top, full pink print skirt and white heels," I said. "I couldnát take my eyes off her as we walked up the steps from the train."
"What do you mean 'full skirt?'"
"Not a mini. It came down just about knee length and kind of puffed out, instead of clinging to her legs."
"Oh." She looked at the clock. "Our session is over. I'll see you next week. Oh wait...can we make next week at 7:30, instead of the usual 1:00?"
"Sure," I said. "Is there a problem."
"Oh, no, I just have another patient who asked for a lunch appointment. If it's a problem, I'll tell her no."
"No problem. Just curious. See you next week."
Jennifer had been my therapist for eight years, since before I got married. I'd been having marital problems for about a year. I began feeling like Jennifer was getting frustrated by my complaining. I kept expecting her to say, "Shit or get off the pot." But therapists never do that. I once asked her if she was annoyed, and she gave one of those classic therapist answers like, "Well, do you think I should be annoyed?" I guess that something you learn in training - "Always answer a question with a question." Anyway, for the past few weeks, we'd been talking about what life would be like if I left my wife. She asked me to fantasize about people I saw on my way to work. I actually found it liberating to imagine picking up someone on the train. Realistically, it would never happen. It takes a certain alpha male type to do that and I, unfortunately, am not that guy. Still, it was kind of cool to imagine myself working my magic on the people I saw.
The next week, I arrived at Jennifer's office at 7:30. The receptionist wasn't there, so she buzzed me in.
"Where's Cheryl?"
"Oh, she gets off at 5:30. It's just me," she said. "Come in."
I looked around the room, and saw a garment bag hanging from the coat rack. "Oh," I said. "Do a little shopping?" I was just making small talk.
"Sort of," she said, as she unzipped the garment bag. "This is for you."
When she opened the bag, I saw a blue sheath dress. It appeared to be slightly higher than knee length, and had white piping around the collar and hem.
"Uh, excuse me?" was all I could stammer. "What do you mean , 'for me'?"
"Strip," she commanded, her tone becoming stern. "This is for you, and so are these," she said, handing me a Victoria's Secret bag with a bra, panties and stockings inside.
"What the hell is going on here?" I yelled. "What the fuck are you trying to do?"
"Look," she said flatly. "We've talked about your crossdressing fantasies for months. But something always seems to hold you back. You once asked me if I was annoyed. Well, I am. For you. You need to do this for you. And for me. It'll help the process."
I began to strip. I know this seems like I gave in too soon. But, secretly, I had always fantasized that Jennifer would lead me to this. Not in a dominatrix kind of way. More like a helpful friend or older sister.
"Could you at least turn around?" I asked. "This is kind of embarrassing."
She laughed. "I think we're kind of past that, don't you? You've bared your soul to me. I would think your body wouldn't be an issue, at all."
I stripped. My cock shrank to nothing in abject fear.
"So, put on the bra and panties first."
I fumbled with the bra. I could never do it smoothly with the few women with whom I had been, and this was a lot more nerve racking.
"I guess you won't be applying for a job with a bomb squad," Jennifer said with a smile.
I turned angrily on her. "I'm glad this is so funny to you. Really professional."
She came over and began adjusting the bra. "I'm sorry," she said, putting a hand of my shoulder. "I saw you were tense, and was trying to lighten the mood. You're right, though. I crossed the line, and again am sorry. 38 chest, though. I was right."
"Well, if this ever falls through, you can get a job at a bra store. Or maybe guessing weights at a carnival."
"OK, now for the stockings. Sit down, and let me show you how to put on stockings." I sat.
"First, ball the stocking like this. Then point your toe towards me," she said and began slowly running the stocking up my leg. My cock began getting hard.
She glanced at it. "Calm down, that's not what this is about, Steve. Besides, I'm married."
Well, my cock inexplicably complied. It must have been that older sister/mother thing I had developed with her. "Stand up," she said. "Let me put these in," she said, taking out a set of silicone bags and slipping them in the bra.
"What are those?" I asked.
"Breast forms. You surf those websites, and you didn't know what these were," she said, raising an eyebrow.
"I thought that's what they were. I just wasn't 100% sure. So what size am I?"
"D cup. With a 38 chest, you really couldn't be much smaller. Now, put on the dress."
I stepped into it, and slid it up.
"Put these on," she said, handing me a pair of black slingback pumps with a 3" heel. They were a little tight.
"How did you guess my size," I asked.
"Just lucky," she said. "Stand up." I stood up "Perfect," she said. "Oh wait, one more thing," she said, pulling out a tube of lipstick. "This will complete the look," she said.
"Maybe not. I think Beth will notice, don't you?"
"Don't worry," she said with a grin. "We'll take it off before the end of the session. Now look at yourself," she said, pointing to a mirror on her door. "What do you think?"
I looked at myself. "I look like a guy with tits wearing a blue dress and lipstick."
"That's it? Anything else?"
"I like the dress."
"Why?"
"It's a good length. Very classic looking. With the breasts, it falls right too."
"Hmmm," she said. "Anything else?"
"The heels."
"Why?"
"They make my legs look longer, and give them a nice shape."
"You do have nice legs, Steve. Most women would kill for legs like that."
"Boy, thanks. You sure know how to turn a guy's head."
"You pointed it out. Not me. What's your name"
"Steve?"
She sighed in exasperation. "You know what I mean."
"Ummm, Jennifer?"
Again, she sighed. "PRO-jection. Try again."
"Jessica," I said. "I always liked that name."
She looked upward. "Good. Well, Jessica, would you like to begin our session?"
"Yeah."
"Girls don't say, 'yeah,' they say, 'yes, please.' Would you like to begin our session?"
"Yes, please."
"Well, Jessica," she said, going to the door, "I have a surprise for you. Tom, come here please."
In walked a 6'4" brown haired, green eyed guy with a good build. You knew he was extremely well built, because you could see it through his shirt. "Jessica, Tom. Tom, Jessica," Jennifer said, with a leer. "I'll be back in twenty minutes," she said, walking out the door.
"Whoa, Jennifer," I said. "What the hell's going on here?"
"You and Tom can talk," she said, closing the door and leaving.
"Uh, look, Tom," I said, backing up against a wall. "I don't know what Jennifer told you, but, uh, nothing personal, I'm, uh not interested and, as you can see, I'm a guy, and..."
He put his finger to my lips. "Shhh, I know who you are. You don't. But I do. And I like a girl with something extra." He began unbuttoning his shirt. His shirt hadn't done him justice. He had the most gorgeous set of six-pack abs I had ever seen, and his arms were perfect. Muscular, without being cartoon-like.
"What the hell are you doing," I said weakly. "I said I wasn't interested..."
"Really?" he said, with a wink. "I can't help but notice you looking at my stomach. Do you like it?"
"It's, uh, very nice. Do you do crunches, or situps, or..." I began babbling. I averted my eyes downward. I tried not to look at the bulge in his pants, but it was kind of hard to miss.
"Yeah," he said, "You're not the least bit interested," he said, pinning me up against the wall. Even in the heels, he was still 2" taller than me.
"Hey, stop. I'll hit you," I said, as he thrust his tongue in my mouth. "Mmm," I moaned, kissing him back. He put a hand under my dress, and began massaging my thigh. I don't know what I was thinking, but I began playing with his abs. I had wanted to touch those abs from the minute he walked in.
"Still not interested?"
"Shut up," I protested, as he moved his hand from my thigh to my crotch.
"Oh, yeah, Jessica," he smirked, "I can see how uninterested you are. Why don't you show me how uninterested," and he began kissing me again. A gay friend had once told me you hadn't lived until you'd been kissed by another man. He was right. My hand moved from his abs into his pants.
"Ooooh," I said, playing with his cock. "Can he come out to play?" I said, unzipping his pants.
I pulled down his briefs, and an 8" cock sprung out. My throat got dry and tight and my pulse began racing. My mind said, "Run," but my body wanted to stay. I started running my hand all over it, and began to go to my knees. Tom stopped me.
"Hold on," he said. "Let's go slowly. Let me show you what I can do first," he said, unzipping my dress. It fell to my ankles. "Now, lay down to the couch," he commanded.
I laid down on the couch, and he climbed on top of me. He began playing with my breast (forms) through the bra. Even though they were fake, I swear I felt my nipples getting hard. "Please, Tom, please let me touch it."
"No," he said, "I'm going to please you and then, and only then, will I let you please me," he said. He moved his hands down, and began massaging my ass while kissing my inner thighs. I was shuddering.
"Try not to cum," he said gently. "It'll be that much better, if you wait. Now, roll over."
I did as he said. He began massaging my back. I never liked massages. They made me more, not less, tense. But, something about his strong arms made me melt. "Mmmm, that feels so good," I whispered. Suddenly, I felt something rubbing against my ass. He began moving his cock around my ass. Beth always liked when I did this. I never understood why. Now I did. The feel of his cock through the satin panties was unlike anything I had ever experienced. It was forceful yet gentle. I kept moaning and whimpering.
"Well, clearly, you're still uninterested," he said.
"Shut up, and do it faster and harder," I said. He complied, thrusting harder and faster.
I couldn't hold back any longer. I began making high pitched squeaks, "Unh, oh, g-d, yes..." I came, but it felt more deeper than any orgasm I had ever had. I felt it in the pit of my stomach. Tom stuck his hand in my panties, and came up with a finger full of cum.
"Lick it," he said. "I want you used to the taste." I gladly licked his finger, running it in and out of my mouth.
"Now," he said, with a devilish grin. "My turn to be pleasured. Or is it yours...Jessica?" He straddled my face so that his cock was looking me in the eye.
I still felt like I should run away. But, I couldn't. Instead, I cupped his balls in my hands and began massaging them. "Oooh," I said, "Can I play with your balls, little boy?" After a minute, I said, "Let me get up. You sit right there." I got on my knees, and stared directly at his crotch. I thought I'd go blind, like if you look directly at a solar eclipse. Instead, I began taking him little by little into my mouth. "Mmmm," I mumbled, taking him deeper and deeper each time. After what felt like an eternity, I felt his cock shudder. Before I could move away, I felt him shoot his load into my mouth. At first, I gagged. But, then, I began greedily drinking it in. After he shot his load, he pulled out. He stood up, pulled up his underwear and pants and began buttoning his shirt.
He opened the door, and said, "Okay, Jennifer, we're all done now."
Jennifer walked back in, with a huge smile. "Thanks, Tom."
"Thanks, Jennifer." He leaned over and kissed me on the mouth. "Thanks, Jessica." He walked out, and closed the door.
"Put your dress on, and let's talk," she said.
I put the dress on and sat down. "What the hell just happened?" I demanded.
"What do you think just happened?"
"No offense, Jennifer, but cut the therapist-speak. I come for my usual session, and you force me into a dress and next thing I know I'm being assaulted by some guy."
"Force. That's an interesting choice of words. Did I in anyway exert physical pressure upon you?"
"Well, no."
"Did I threaten to falsely accuse you of a crime?"
"Of course not. Where are you going with this?"
"I'm just questioning your terminology, Steve."
"Well, I mean, you're my therapist. You know I trust you implicitly and I just thought that maybe if you thought this would be a good idea, then..."
"So, if I told you to jump off the Brooklyn Bridge..."
"Ha ha," I said flatly. "I know we've talked about me seeing you as a maternal figure, but that's a little much..."
"Fine. Let me ask you another question. What kind of dress is that?"
"A sheath."
"Sheath. Yes. And tell me about the shoes."
"Black slingbacks. With a 3" heel."
"Do you think other men know that? If I asked my husband those questions, his responses would have been 'blue' and 'black.'"
"So what? We've covered my crossdressing fantasies. What does that have to do with this?"
"You've talked and talked about going to a fantasy facilitator. You've told me about your fantasy of having a female friend who helps you get dressed. I decided it was time to dress up or shut up. And, by the way, you were right. That dress did look very good on you. Baby blue is perfect for your coloring."
"Fine. That doesn't excuse Tom. I never said I was gay and I certainly didn't expect to be assaulted."
"Assaulted. Another interesting choice of words."
"Oh great, this again," I said, with my eyes rolling.
"Well, Jessica," she said, eyes rolling, "I was outside the whole time, and I didn't hear you scream for help. If you were really being assaulted, you would have screamed."
"Do you blame rape victims who are forced against their will and can't scream?"
"Oh please, Steve," she sneered. "Did Tom threaten to hurt you if you screamed?"
"Um, no."
"Did you want to scream?"
"Maybe not," I said, staring at the floor.
"Did you try and hit Tom to stop him?"
"He's like 3" taller than me, at least."
"Did you try and leave the room?" When I didn't respond, she said, "Oh yes, I see the threat. I also couldn't help but notice that, when I came in, your dress was on the floor. It doesn't appear to be ripped, so am I safe in assuming you took it off voluntarily?"
I blushed. "Well..."
"And I can't help but notice that the lipstick you were so worried about seems to be mostly removed."
"OK, I get your point."
"And I didn't notice too much on Tom's face. Would I have found some in another place, Jessica?"
"This is so embarassing," I said, "I never thought of myself as gay," and with that I told Jennifer the entire story. She made me describe every thought, feeling and sensation in excruciating detail. She especially had me linger over my desire for Tom's abs. I told her how much I loved touching each and every muscle in the six pack, and how absolutely carved his chest and arms were. I told her how I hate massages, but didn't want to Tom to stop kneading my back with those magnificent arms of his. I told her about how I wanted to run, but got dry mouth and a racing pulse I got when I first saw Tom's penis. It almost felt like she was living vicariously.
"You know what's amazing to me," she said, after I finished breathlessly. "How alive you were when you told that story."
"What do you mean?"
"When you talk about your sexual experiences with women, you seem disembodied. Like you were physically there, but mentally elsewhere. But when you talked about Tom, you became animated. It was like a different person than the Steve of the past eight years."
"I don't like where this is going, Jennifer," I said, warily.
"Steve," she said, patting my hand, "I'm not judging you. But let me offer some observations. We've been working with 'real-life' fantasies for the past few weeks, right?"
"Right. Where is this going?"
"When you talk about women, you say how beautiful they are. But you spend as much if not more time focusing on their clothing than them. Do you remember what we ended last session with?"
"The woman on the stairs."
"Yes, the woman on the stairs. You told me she was wearing," as she looked at her notes, "a white short-sleeved top, full pink print skirt and white heels."
"I remember."
"I hate to keep going back to the comparison, but my husband would not remember those details. He'd remember that she was wearing heels, and if she had been wearing a short skirt, but he wouldn't remember colors or types of clothing."
"So, your husband's not observant. Sorry for you."
"That's not what this is about, Steve. I've noticed that, even when you talk about a woman's physical attributes, it's usually part of a discussion of their clothing. Like, 'she was wearing a yellow shift that really accentuated her ass. Or the boots really drew attention to her gorgeous legs.' Quite frankly, it's like listening to one of my girlfriends cut apart a woman we've seen."
"So what, I'm a girl? Thanks, Jennifer. That makes me feel sooo much better."
"Look, Steve," she said sternly. "That's not what I'm saying. Stop projecting your insecurities onto me and listen. I'm going to ask you one question, and answer me truthfully. When you see a beautiful, well-dressed woman on the street, what do you want? To get in her panties, or to get IN her panties."
"Come on. What do you think? I'm married, for chrissakes. And it's not like my parents don't have gay friends. If I was gay, I could be out. I'm not out. Therefore, I'm not gay. See?"
She laughed. "Now, that was an extremely convincing argument. We've talked about this before. You've told me about wet dreams you've had..."
"Hey," I protested. "You said those don't necessarily mean anything. I'm so glad I trusted you. Thanks a hell of a lot."
"First off, you just issued the ultimate qualification - 'necessarily mean anything.' I've asked you to describe the guys in these dreams. You never mention clothes and can, in fact, rarely describe their faces. Instead, I hear about their chests. Their arms. Their penises. And their abs. Boy, you sure go on about abs. I haven't decided what that means yet, but you have a thing about them."
"And that's why you chose Tom. Is this a DSM-approved therapy, Jennifer? Bringing in hunks to seduce closet drag queens?" I said sarcastically.
"First off, Steve, try to limit the pyschobabble. A little knowledge is a dangerous thing," she said drily. "Second, hunk, huh? Another interesting choice of words."
"I was being sarcastic."
"Oh really? If I called Tom in, would he say you weren't satisfied with his service?"
"No," I replied.
"Would he be lying?"
"Great," I said, with my tears in my eyes. "I was a married man this morning. Now, I'm some kind of drag queen cock-sucking bottom. Beth will be so thrilled. My life is over."
"No," she said, handing me tissues. "Your life is most definitely not over. First off, being turned on by women's clothes does not mean you're now a female impersonator. It's something that turns you on sexually, and you should be able to find someone who lets it be part of your sex life. You said you approached Beth about once, and she shut it down completely. Do you think that's fair?"
"I didn't think I should force something she hated."
"Fine, do you think sex is satisfying to her?"
"We've covered that..."
"Exactly. Do you think it's fair to her to be with someone who's not psychologically present during sex? Shouldn't she be able to be with someone who is?"
"Well, no."
"Look, I'm not saying to go home tonight, and say, 'Guess what honey? I'm gay!' I think you need to figure things out first."
"Great. Turn my life upside down in one session, and then tell me hold up. That's really fair."
"That's not what I said. I think we both know how this will end, but you don't just upend someone else's life on a one shot deal, Steve. You need to process this, and connect with your feelings before you go and do something."
"I know. You're right."
She looked at her watch. "I'm sorry to end like this, but session's over. I'll see you next week. Regular time," and she left me. I began putting on my clothes, wondering what the hell was going to happen next.....
[to be continued, if there's interest.] (Probably not since this was originally posted 2004-11-11 -- BCEditor)
“Eight years,” I thought as I left Jennifer’s office. “Eight. Years. Eight. Fucking. Years. And she pulls this shit. Who the fuck did she think she was? If I wanted this, I would have gone to a dominatrix. It would’ve cost me a hell of a lot less, and I wouldn’t have wasted all those lunch hours.”
I could feel myself scowling and clenching my fists. I must have made some sight walking down Broadway to the train. “Fuck her. Just fuck her,” I thought. A woman stared at me. I glowered back. Out of the corner of my eye, I saw her shake her head as she scurried off.
As I passed 74th Street, I heard a woman’s voice, “Steve?”
I snapped out of my misery, “Huh? Yeah...holy shit! Donna? Donna Amalfitano?” I said with a smile. Donna had been the high school and community college girlfriend of my friend Dan Quinlan. We all hung out together when I was back from college on breaks.
“Donna Hicks, now. But yeah, it’s me.”
“Oh wow, it’s been, what, like fifteen years? I thought you moved to San Diego back in 1990.”
“I did. But I came back. My job gave me a chance to come back, and I missed my family. I have a niece and nephew now, and I felt like I was missing out on their lives being cross-country.”
“That’s cool. How’s your family? How’re your mom and Nick doing?” Donna’s dad died when we were juniors in high school.
“Mom’s fine. Nick just got promoted to sergeant on the force.”
“The force? As in police force? Nick? Your brother Nick?” Nick had always had, let’s just say, a difficult relationship with the law.
“Yup, he’s a cop now. Has been for twelve years.”
“Wow, I guess people can change, huh?”
She laughed. “I didn’t say he’d changed. I said he was a cop.”
“Oh. Enough about him. So tell me about the lucky Mr. Hicks.”
She blushed. “Thanks, Steve. I appreciate that. Not much to say. We’re divorced. And you?”
I held up my left hand and tapped my ring. “Seven years or, as I like to put it, two wonderful years.”
“Really,” she said, arching her eyebrows. “That’s, uh, great.”
“What?” I said, girding myself. “What does ‘uh, great’ mean?”
“Nothing,” she said. “Forget I said anything.”
I knew what she was talking about. Back when I was a freshman in college, she attended community college with my friend Quinlan. His given name was Dan but, at some point in high school, everyone started calling him just Quinlan. Teachers, his brother, everyone. Only his mother and father called him Dan. Anyway, I was back on winter break my sophomore year and we were all hanging out.
“Hey, Steve,” she asked. “Do you know anything about American History from 1900 to the present?”
“Kind of a broad area, but yeah I basically do. Why?”
“Well, I’m taking this history class, and my final’s coming up.”
“OK, what do you need? Help studying.”
“Yes,” she said, suddenly grinning. “Actually, I have a better idea.”
I rolled my eyes, “This should be good.”
“We’ll dress you up like me,” she said, cracking herself up. “Leggings, a big shirt. A wig. Makeup. Noone will know.”
I began to sweat, or at least feel like I was. I regained composure. “Great idea. How do you suppose will pull this off? I’m, what, 6" taller and like 50 lbs. heavier than you? Besides, what do we do about Mr. Lucky down there?” I said, pointing at my crotch. Deep down, I was really excited. I wished we could do this.
She pulled out a compact from her bag, and began dusting my face with powder. I was getting more and more excited. “Oh, we could pull this off. So you’ll wear a skirt instead,” she said, looking down at my rapidly growing member. “I mean, if that wouldn’t bother you too much.” I blushed. I knew exactly what I’d wear. She had a black cotton miniskirt and boots that I loved. That, her cute blue top, some bracelets. I was getting really excited.
She giggled. “You would be really cute. And look you won’t need blusher.”
Just then, Quinlan walked in from the bathroom, “What’s going on?”
“I had this great idea for Prof. Rabinowitz’s class,” she said, laughing. “We’re going to dress Steve up like me, and he’s going to take the final.”
“That’s a good idea,” he laughed back. “I mean, so long as I don’t have to sleep with him after or anything.”
I got up, and punched him in the arm. “Yeah, like I’d sleep with you, you dickwad. This is nuts,” I said, protesting too much. “I’m going to wash my face.”
Donna came over. “I was just teasing, Steve.”
“Yeah, I know,” I said. “Besides, I’m a lot of things, but an attractive woman isn’t one of them. Anyway, I’ll help you study, if you want. Let me know when.”
“How about tonight? The test is day after tomorrow. I’d really appreciate it.”
“No problem. Not like I have plans.” Which was, unfortunately true. I got together with friends from college on the weekends, but during the week I reverted to my high school loser self.
That night, I went over to Donna’s to study. I rang the bell. Her brother Nick answered.
“Hey, Nick, how you doing?”
“Hey, Donna, your girlfriend is here,” he sniggered.
She came down the stairs, and punched Nick in the stomach. “Shut up, asshole. Hi, Steve. Thanks for coming over.” Nick stared at me, shook his head and said, “I’m going out. Ladies.”
“You didn’t have to do that,” I said. “I don’t put too much stock in Nick.”
“He’s just a dick. Let’s go to the kitchen.”
We studied for several hours. Donna wasn’t stupid, by any stretch of the imagination. She just had no ambition, which was kind of to be expected. The women in her family worked as secretaries and store clerks, and said of any woman who tried to do better “Whaddaya think you’re special?”
After about three hours, she said, “You know, Steve. You’ve actually made this interesting. I think I could do well on this test.” She leaned over and kissed me chastely on the cheek.
I blushed. “Thanks, this stuff really interests me. Besides, you’re smarter than you think.”
“Thanks,” she said. “You’re really a great guy. And I want to thank you.” She reached into her purse.
“You’re welcome,” I said, “You don’t have to give me anything. It’s really no big deal. I like helping you.”
She pulled out her address book, and wrote a name down on a piece of paper.
“What’s this,” I said, looking at the paper.
“It’s my cousin Todd’s number. He’s a sophomore at Yale. I told him all about you. He’s really excited. He likes intellectuals, especially blue eyed ones.”
Subconsciously, I wanted to squeal with delight like her girlfriend. I wanted to ask her all about him, what he looked like, what he liked to do and all of that. But I was in deep denial, so instead I growled, “What? What’s this supposed to mean?”
“I just thought...” she said.
“You thought wrong,” I snapped. “I’m not gay or anything. What the hell made you think that?”
“I’m sorry,” she said. “It’s just that you’re smart and funny. And no one’s ever seen you with a woman. I mean, you don’t try and hook up when we’re all out or anything.”
“So what, Dean and Lucas never hook up. Do you think they’re gay too?”
She rolled her eyes. “Please. Come on. Lucas tries to hook up, but he’s not exactly fuckable, if you know what I mean. And, Dean is, well, Dean. He’s in his own world. Don’t lump yourself in with those two. You’re better.”
“Thanks, but even still...maybe I’m just shy, did you ever think of that?”
“Maybe, but you talk to me and Erica. You’ve talked to my friend Sheri. She was into you, you know. All you had to do was make a move, and you didn’t.”
“First off, I talk to you guys because you’re my friends’ girlfriends, so I don’t feel subconscious or anything. Plus, Sheri was really into me? Really?”
She laughed, “OK, maybe you’re not gay. Just dense. I mean, if you were gay, we’d be cool with it.”
My eyes widened. “Oh, jeez, we? Who else did you share this with? Not Quinlan, please?”
“No, no,” she said, holding my hand. “Quinlan would be all freaked out. I told Erica.”
“Oh no, she’ll tell Jason, and he’ll tell Quinlan,” I groaned.
“No, she won’t. She understands. She’s totally cool with it...”
“There is no it to be cool with, Donna. OK?”
“OK, OK. I’m sorry. I didn’t mean to hurt your feelings. I just thought...”
“I know. Next time, remember, I like women.”
“Yeah, OK. Whatever...”
After that, whenever we all went out, I made a real effort to try and “hook up,” or at least look like I was. It felt like I was acting, and acting poorly, and not surprisingly I always struck out. I’d catch Erica and Donna out of the corner of my eye, staring at me and shaking their heads. Whenever I’d come back to the table, Donna would always say something like, “Boy, Steve, you have no luck with women. I wonder why. Just bad luck, I guess, huh?”
“Hey, Steve,” Donna said, snapping me out of my reminiscence. “I bet I know what you were thinking about.”
“Yeah, yeah.”
“Do you live around here?”
“No, actually coming from therapy. My shrink’s on 72nd.”
“You’re in therapy, huh?”
“Yeah, everyone in New York is. You’ll start soon. Or else you’ll have to move back to Jersey. It’s an obscure law.”
“No kidding,” she laughed.
“Yeah, anyway, you look like you were on your way. Let me give you my card,” I said, fishing through my briefcase. “We should get together sometime.”
She looked at the card. “Attorney, huh? I figured you’d do something like that. Actually, you would’ve been a great writer too.”
“Thanks. All lawyers are frustrated writers. Except for litigators. They’re frustrated actors.”
“What kind of law?”
“Municipal bond financing.”
“Wow,” she said, “That sounds, really, uh, exciting.”
“Yeah, I know. It’s not. But good job faking it. All those years with Quinlan must’ve paid off.”
She laughed. “Actually, what are you up to now? I mean, if you don’t have to get home or anything.”
“I was just going to get something to eat. My wife goes out with her friends on Wednesdays.”
“Mind if I join you?”
“That’d be great. Otherwise, it’s just me and the New Yorker.”
“Terrific. How about Italian? Oh, shit...not you, too, Steve,” she said, staring at my face.
“What? What me too?”
“The lipstick, Steve,” she said, angrily, “Therapy, huh? Yeah, my ex used to get the same kind of therapy. I guess I was wrong about you.” She turned to walk away.
“Wait,” I said. “It’s not what you think. Believe me, it’s not.”
“Oh really,” she snarled. “What is it then?”
“This is really, really private,” I said, with tears in my eyes. “I don’t want to talk about it on the street. Please believe me.”
I must have convinced her with my tears. She said softly, “I live on 75th and Amsterdam. God help you if you’re fucking with me, though.”
“Believe me, I’m not,” I pleaded. “When I tell you what’s wrong, you’ll know.”
She cracked a smile, “Well, this is getting good.”
I have no idea why I wanted to tell her. Maybe it’s because of what had happened between us. Maybe it’s because I knew her but, fifteen years having passed, I didn’t really know her. Maybe I just needed to tell someone, anyone. We came to her building, and walked up to her apartment.
“Home sweet home,” she said, flicking on the light.
It was a small one-bedroom. Very tastefully decorated. Very feminine. Not Laura Ashley explosion feminine, but you knew a woman lived there. Actually, if you knew Donna, you knew she lived there.
“Nice place,” I said, looking around. “I like your style. My wife’s not much for decorating.”
She gave a half smile. “Thanks. I figured you’d like it.”
I laughed, “I won’t even say, ‘What’s that supposed to mean.’”
“So, what’s with the lipstick?”
“Can I get a drink first?”
“Wine?”
“Great.”
She poured two glasses, and gave me one. “So,” I said, “this is good wine. What kind is it. And, boy, these are nice glasses. Crate and Barrel. I like Crate and Barrel.”
“Nice try, Steve. Speak or get out.”
With that, I let loose. I told her all about my fantasies. I told her about the dress. I told her about Tom. About how his massage made me feel better than I had ever felt. About his chest. About his gorgeous abs, and I how wanted to touch each muscle forever. I began telling her about how he penetrated me through the panties. I told her about blowing him. Everything.
“Whoa,” she said when I finished. “Well, that certainly explains the lipstick.”
“Shit. I’m sorry. I should never have said anything.”
“It’s OK, Steve. I’m not so sure what I think of your therapist though. That’s a little, uh, fucked up, don’t you think?”
“I’m not really sure what I think, or what’s right, you know.”
“Go with how you feel. How did it feel when he penetrated you through the panties?”
“Oh, jeez. This is, uh, god, shit. Never mind.”
“Speak,” she demanded. “Just tell me what you’re feeling.”
I stared at the floor. “I felt it in the pit of my stomach. I’ve never cum like that,” I said, blushing.
“You are so lucky, bitch. Most women rarely ever have orgasms like that. And you got it with your first try.”
“Great. I’m a woman now. Just what I wanted to hear.”
“Stop it, Steve. How was everything else? What did you think of the blow job?”
“Taking notes?”
“Stop being so sarcastic. How was it?”
“I gagged.”
“Don’t worry. Everyone does. It takes getting used to.”
“There’s no getting used to anything. It was a mistake.”
“Was it? Come on.”
I began bawling. “What the hell am I going to do?”
She came over and hugged me. “It’s OK, Steve. It was OK fifteen years ago. It’s OK now.”
“But, it’s not fifteen years ago. It’s now. I’m married. I have a job. I have a life. And this will fuck it up royally.”
“It will not, Steve,” she said, continuing to hold me. “I know your family. They’ll support you no matter what.”
“It’s not that simple...”
“Steve, I know. Remember my mom? Mass every day? What do you think she did when I told her I was getting divorced?”
“It’s not the same. It’s not like you had to announce to the world ‘I like sucking dick.’ Besides, I didn’t notice eleven states passing constitutional amendments against divorced women...”
“Yeah, OK, I see what you’re saying. But, still, you need to be happy. You need to be who you are.”
I started bawling again. “I don’t know who I am anymore.” She came over, held me and wiped a tear from my face. She leaned in and kissed me gently on the lips. “There, there,” she said. Then, she kissed me again, harder. I opened my mouth and our tongues began probing the inside of each other’s mouths.
She pulled back. “You kiss nice. Soft. Gentle. I like that.”
“Boy,” I said. “Soft and gentle. I feel good now.”
“Shut up,” she said, kissing me full on the mouth again.
I stopped. “I don’t know. I don’t what else I am, but I know I’m still married.”
“That’s fine,” she said, coyly. “Whatever you want.”
I grabbed her, and began kissing her.
“Gently, Steve. I liked it gently. Let me control everything.” With that, she began kissing me forcefully. She put her hand on my groin. “Looks like someone still likes women, too. Come this way,” she said, wagging her finger towards her bedroom.
I shouldn’t have done it. I owed Beth that much. But I did. I went with her.
She pushed me onto the bed, and began taking my shirt off button by button. She ran her fingernails up and down my chest. “Mmmm, do you like, Stevie? Mmm, do you, little girl?”
“Unnnh. Yeah. Mmmmm.”
“Yes, good little girls say ‘yes.’”
“Oh, yes. Donna. Oh, yes,” I moaned.
Then she unbuttoned my pants. “Oooh, someone’s enjoying himself.” I tried to sit up, and take off her blouse. “No, no, no,” she said, pushing me backward and straddling me. “I’m in control, you little, what did you call yourself, bottom. I like that. You’re my little bottom.” With that, she reached up under her skirt and pulled off her panties. She threw them at me. “Smell. You like?”
I took in her musky scent. I loved it. I had always liked going down on Beth. She didn’t like it though. “Mmmm, you smell great.”
She brushed my penis with her vagina.
“Please, Donna, please,” I cried.
“No, no,” she said, inching her way up my chest, “Remember, you’re the bottom.. I’m the top. You will do what I say when I say it.” With that, she put her pussy over my face. I began licking her clit.
“Faster, now slower, now faster,” she said, as she fingered her nipples. “Ooooh, that’s good. Oh, yes, Stevie girl. Oooh, you know what to do.” She jerked involuntarily. “Yes, yes. Yes, yes. Oh, Stevie.”
She crawled off me, and reached into her nightstand. She pulled out a baby doll nightie and a condom. “Put these on.”
I put on the condom. I held up the nightie, “But...”
“Little girl, do you want me to do something about that?” she asked, pointing at my penis.
I reluctantly put in on. It was tight, but it fit. She pushed me onto my back. “Now, put your legs on my shoulders. I’m going to fuck you the way you need to be fucked.” This was one of my deepest fantasies, to have a woman fuck me while I was in a nightie. If she’d throw in handcuffs, I would’ve truly been in heaven. I kept expecting to wake up.
She began rhythmically pushing herself on and off my penis. “That’s good,” she said. “Feel the motion. Start pushing back with just your little pussy there. That’s right. That’s right.” Then, suddenly, she began putting her finger in my asshole. I jerked.
“Calm down, little girl. Relax. Do you like it?” she said, thrusting it in out, while we rocked in time.
“Oh, yes. I like it,” I whimpered.
“Which do you like better?”
“Both, I like both.”
“Say, ‘Fuck me. Fuck me harder.’”
“Fuck me. Fuck me harder. Please fuck me.”
“Nice. I like that.”
“Who’s my Stevie? Who’s my little girl?”
“Me, Donna. Me. Please don’t stop,” I said, arching my back.
“Good girl,” she said. “You know just how to please me.”
I jerked my back one more time, and came violently. “Oh, Donna.”
“That was a quite a little performance there, Steve. You are one little rug muncher. If you switch sides, it’ll be a real shame. Although, there will be some lucky guys.”
That snapped me out of the post-coital glow. “Oh, shit. What did we just do, Donna? Oh, god, look at me,” I said, turning to the mirror.
“Do you like what you see?”
“It doesn’t fit right. But, I like the way it looks and feels.”
“There’s nothing wrong with that.”
“Would you be with someone who liked it?”
“I just was.”
“Pity fucks don’t count.”
“I don’t do pity fucks, Stevie. Don’t sell yourself short.”
“What the hell did we just do?”
“Are you happy at home, Stevie?”
“Not really.”
“I’m no shrink, but you seem lost. Like someone trying to find his way.”
“Wow, that’s deep...” I said, with a smile.
“I’m trying to help.”
“Sorry. You’re right, though.”
“How many women were you with before Beth?”
I didn’t answer. I looked away.
“Were you a virgin?” she said.
“No.”
“Don’t lie.”
“Yes.”
“Whoa...sorry, that was mean. How many men had you been with?”
“Before today, none.”
“Wow, you really don’t know what you are, do you?”
“I just want to be happy. To be with the right person. Whoever, or whatever, that is.”
She kissed me again on the cheek. “I want to help you, Stevie. Figure out who you are. Whoever you are, I like you. I always have.”
“Thanks,” I said, “What the hell do I do now.”
“Go home. Don’t do anything rash. If you need anything, call me.” She took a piece of paper. “Here’s my number.”
“Thanks,” I said, taking off the nightie and getting dressed. “Now, I’m really fucked up.”
“You’re just confused. Go.” she said, putting on a t-shirt and shorts.
As she took me to the door, she kissed me again. “Seriously, if you need anything, call. By the way, Todd’s still available.”
“Ha, ha,” I said, with a smile. “Besides, how good could he be if someone hasn’t snapped him up yet.”
She laughed, “You are such a bitch, girl. Leave,” she said, pushing me out the door. “Anytime you want to go down again, let me know. You have one hell of a tongue,” she said, as the door closed.
I walked downstairs. The world seemed all at once better and worse. What the hell was I going to do now?
{to be continued, if there’s interest.}