Lynn Comes Out

It started kind of strange. I am or at least was Len or Lenny – Leonard to my mother – a guy in my early 20s, kind of short and slender. I had a sister, Karen who was a few years older than me. She’d had a nasty breakup with a fiancé, and stayed with me for a while when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a nice little brother, I let her have the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving little room for my clothes. Beyond that, we had to share one tiny bathroom, in shifts, since there was no way we were going to be in there at the same time – too small and too weird.

Karen stayed with me for about six months before getting her own place and moving out. Her place was smaller than mine, so while she took most of her stuff, she had more clothes than she had room for in the new place. She didn’t want to donate them, so she asked if she could leave them at my place until she could afford a bigger place. Again, being a nice brother, I let her do it.

Karen left behind all manner of things, skirts, dresses, blouses, bras, panties, shoes, makeup, and all that. After I while I got fascinated with it, which I guess was my first mistake. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.

I started by just touching her clothes while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my head while doing myself. After a time, that didn’t turn me on the way it once did, so I even began putting on some of her clothes. That seemed to be a bigger turn-on and her clothes seemed to fit, since we were almost the same size.

As time went on, I’d dress up completely in Karen’s clothes for my self-a***e sessions, and even left them on after I’d cum. I began to play with it all a little bit and even began to use some of the makeup she’d left behind. I’d pad her bras with socks or whatever, put on panties, a skirt, blouse, and shoes, then brush my hair in a more feminine style and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no girls willing to help me. Before long, I’d come home from work, dress up all girly, and prance around my apartment before getting myself off. I’d even wear one of Karen’s old nighties to bed afterward.

I had a few friends who I’d hang out with occasionally. One of them, who I’d known since high school was Matt. He was always the popular sort, never had any problem getting girls, and often seemed to have one or more hanging off him. He’d take me along as a wingman sometimes, though I never managed to get any girls out of it.

One night he and I were drinking, and I’d had more than I should have, and we began talking. He started telling me about how he got some chick to let him finger her in public in a restaurant. He said they’d also gone to a movie theater, sat way in back, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.

“Hey, Lenny, what’s the kinkiest thing you’ve even done?”

“Shit, Matt, I can’t get girls to do ordinary shit with me, much less anything kinky.”

“Come on, guy, you must have done something just a little bit out there.”

As I said, I’d had too much to drink, and I confessed to dressing up in my sister’s clothes to jerk off.

“Seriously, Len. Do you just slip on her panties to get turned on or do something more?”

“Sometimes I’ll go full drag, clothes, shoes, makeup, and everything.”

“Fuck, man, that I’d like to see.”

“I don’t know, dude. Nobody has ever seen me that way. I’d be freaked out to have someone see me.”

“Come on, Lenny. You know me. Let me see you dressed up, just one time.”

“Matt, if anyone ever found out, I’d be totally screwed. I’d have to leave town.”

“Lenny, I swear to God, I’ll never tell anyone.”

That was Thursday, and it was already late and I was too drunk and had to work the next day. He asked if I’d dress up for him the next night. I agreed and told him to come by after work on Friday, but to give me some time to get ready.

“Lenny, do you think you can be ready in an hour?”

“I think so. I get home about six, so come by my place around seven.”


The next day I really had some regrets about agreeing to let him see me dressed up. I called him during lunch and tried to back out, but he said I’d promised and he expected me to keep my promise. I was on edge all afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented body wash, shaved my face, legs, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the thought of having this guy see me in my sister’s clothes. I dried my hair and styled it girlish, then put on panties, a bra, a nice skirt, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye shadow, lipstick, and of course I painted my toenails and fingernails.

I wore some low heels with open toes, to show off the toenail polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o’clock. My knees were wobbly as I walked to the door. I looked through the peephole and sure enough it was Matt. I opened the door and let him in.

Matt was gaping and staring as he walked in my place. I closed and locked the door and he turned me around then stepped back to take a good look at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me nervous. He came back in front of me and grabbed me gently by the shoulders.

“Damn, that is hot, girl.”

“I’m not a girl, I’m just dressed like one. I’m Lenny, you know that.”

“The way you look, Lenny doesn’t work. How about I call you Lynn?”

“Okay, Matt, you got to see me, now let me change back.”

“Hold on, Lynn, not so fast. Don’t run off on me already. Come sit on the sofa with me.”

“I don’t think we should do that, Matt. I’m not one of your little girlfriends, I’m Lenny.”

“While you’re like this, you’re Lynn, and I like Lynn. Come on, please sit on the sofa with me.”

“This was a mistake. I shouldn’t have done this. I want to change.”

Matt put and arm around me tight and walked me over to the couch, pulling me down beside him there. He had his arm around my shoulders and seemed to be getting way too much pleasure out of this.

“Lynn, baby, you are one hot fox.”

“Matt, this feels really weird.”

“Not weird, Lynn, just a little kinky, baby.”

“No one has ever seen me like this before. I feel uncomfortable.”

“You shouldn’t be uncomfortable. You look wonderful, one of the sexiest girls I’ve seen in a while.”

“You’ve got lots of girls – real girls, not fake ones, like me.”

“Don’t tear yourself down. Most of those girls have nothing on you.”

“Jeez, now you’re really embarrassing me.”

“Let me take you out to dinner, Lynn”

“Just let me change into some normal clothes, Matt.”

“No, babe, just like this.”

“God, I can’t go out in public like this.”

“Sure you can, baby. You look absolutely stunning.”

“What if someone sees me – recognizes me?”

“No one will recognize you as that nerdy guy.”

“Doesn’t it bother you to be out in public with a guy in drag?”

“No one but you and I will know, and besides I like a little bit of kinky sometimes.”

“I don’t know.”

“Come on, Lynn. A nice dinner, and I’ll treat you the way a lady should be treated.”

“That makes me feel really weird.”

“And maybe a little turned on?”

“I don’t know if we should be doing this.”

“I do, and we should.”

With that, Matt got up and drew me to my feet. He wrapped his arms around me and pulled me close. I think my eyes were the size of saucers and my knees were getting weak as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the door. When we got there, he stopped and turned.

“Do you need a purse, keys, and such?”

“I think Karen left a couple of purses here too.”

“Grab one and your keys and let’s go.”

This was already getting way beyond anything I’d ever intended, and I was really afraid of where it was going to go. Matt went with me in the bedroom, and I went in the closet and found a purse that didn’t look too bad with what I was wearing. I took my keys and wallet and dropped them in the purse before turning to Matt.

“I’m really not sure we should be doing this, Matt.”

“Everything is going to be just fine, Lynn.”

Matt actually had money, which is yet another reason why most of the girls fell all over each other to get to him. We went downstairs to his brand new blue BMW Z4 convertible and he opened the door of the car for me. I managed to sit down in a somewhat ladylike fashion – I don’t think I showed too much. He got in and drove us to a very nice restaurant.

He used valet parking and walked me in, holding the door for me. I still felt weird as shit, but just tried to ignore how I looked and enjoy myself. Matt ordered a nice bottle of wine for us, and I really needed something to drink. I downed my first glass before he’d taken more than a couple sips of his wine. Matt poured me another glass, but I took it a little slower.

The waiter seemed very taken with me, and when he thought I didn’t notice, tried looking down my blouse. Several other men seemed to notice me, which made me squirm in my seat. One guy who works with Matt stopped at the table to talk with us. I’d met him several times before, but he clearly didn’t recognize me.

“Well, Matt, who is this beautiful lady with you tonight?”

“This is my date, Lynn. Lynn, meet Oliver, he ‘s another department manager where I work.”

“I’m so pleased to meet you, Oliver.”

“And I’m very pleased to meet you, Lynn. Matt is clearly a very lucky man. But if you want a change of scenery, give me a call, I’d love to show you a good time.”

With that, Oliver handed me a business card. I think I turned red, but slipped it in my purse.

“Thanks, Oliver, but I’m not really looking for anyone else at the present.”

“Well, Matt, if you get tired of Lynn here, feel free to send her my way.”

Oliver bent down and kissed my cheek before walking off.

“I do not fucking believe that.”

“I tried telling you, Lynn. You are one hot chick. Half the men in this place would dump their date for a chance to take you home.”

“That’s only because they don’t know what I really am.”

We had a lovely dinner and I continued to drink way more than I should have. This whole scene had blown my mind so much I didn’t know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to talk to Matt. We finished dinner and I thought Matt would take me back to my place.

“Lynn, honey, it’s still early, why don’t we go dancing?”

“Are you sure about that?”

“You’re taking a walk on the wild side, just take a bit longer walk.”

Matt wouldn’t take ‘no’ for an answer and drove us to the hottest club in town. This was the sort of place that would never let the likes of me inside. They must have had a hundred people lined up waiting to get in. Matt was obviously pretty well known, and he walked us up to the front, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a drink and then Matt wanted to dance with me. I felt strange as shit, but it was a fast number and I was already half plastered so I went out to dance with him. We danced several fast dances, then a slow number came on. I thought we’d go sit down, but instead, Matt pulled me close to him to dance.

He had one hand on my upper back, holding me tight, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that Matt had a hard-on as he did that. That scared me more than a little, but I wasn’t sure what I could do. I felt helpless as we danced. When the number ended, Matt stopped, held me tight, and kissed me.

My knees got so weak that if he hadn’t been holding me tight, I’d probably have slumped onto the floor. He gave me a long kiss, and to my surprise, I began to kiss him back. I felt conflicted – I didn’t feel like I should be doing this, not with a guy, but I seemed to be enjoying it. We kissed for a minute before he walked me back and we had another drink.

I’d been drinking pretty good before, but I didn’t slow down. I was half afraid of what was going to happen, and felt like I needed to be very drunk. We drank more and danced more, and the more we drank and danced, the more Matt kept feeling me up and kissing me. My mind was blown – Matt knew I was a guy dressed like a woman, yet he was acting like I was the real thing.

As I said, I’d been Matt’s wingman more than a few times, and had seen him this way with women many times before. I also knew that in most cases he ended up taking those women home and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don’t know how long we danced and drank, but by the time Matt was ready to leave, I was really plastered.

I thought Matt was going to drive me back to my place, but instead he drove me to his apartment. As I said, Matt had money, and he had a very nice two bedroom apartment – nice furniture and all that. Part of me hoped that he was going to let me crash in the spare bedroom. Another part of me wanted anything but that.

“Matt, I really need to get home and change.”

“Lynn, honey, there’s no hurry. Just relax and enjoy your walk on the wild side.”

Matt got us each a drink, like I needed any more alcohol, and sat me down on the sofa, sitting right alongside me. Matt put his arm around me and pulled me tight, then began to kiss me. He started just with the lips, then added in some tongue, while feeling up my ass and my fake boobs. I seemed to be enjoying it, but felt that it was wrong.

“Matt, we shouldn’t be doing this.”

“Sure we should. You seem to like it, and I told you I occasionally like kinky shit.”

“I don’t know if I’m ready to go any farther.”

“Lynn, baby, I’ve shown you a good time. I’ve made you feel good. You seem to be getting into this. Can’t you help me feel good too?”

“What… What did you want me to do?”

“If nothing else, can you at least go down on me?”

“You want me to…?”

“Please, Lynn, baby.”

Matt kissed me and stroked my ass as he unzipped his pants with his other hand. He pulled out his cock, which was already hard and standing straight up. He kissed me again, then gently pushed my head down toward his prick. I got close and looked at it. It was long and hard and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the head of his dick between my lips.

Matt moaned and leaned back, still keeping a hand on my head. I let the head of his cock slip from between my lips, before taking it back and going just a little farther with it. I bobbed up and down on his prick, gradually taking it deeper and deeper into my mouth. I’d never had a dick in my mouth before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my mouth and Matt seemed to like it. Some precum came from the tip, and it had a salty taste, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the base of his dick as I sucked the rest of it. By now, Matt was moving his hips, almost fucking my mouth, as he held my head tight.

Matt moaned loudly and got very rigid as his cock erupted in my mouth. He held my head with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for breath, though it took a couple of swallows to get it all down. It gradually eased and I cleaned his dick off as I pulled my head back from it.

Matt pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my mouth as we kissed, but that didn’t seem to bother him. Matt continued to kiss me and I didn’t even realize it as he pulled my skirt up over my ass and began to caress my ass through my panties. He even snuck his hand into my panties and fondled my bare ass.

I don’t know why I didn’t notice, I don’t know why I didn’t stop him. Maybe I was enjoying it all too much, and maybe I was just too drunk. Before I even realized it, Matt had removed my skirt and blouse and was carrying me into his bedroom. I was so far gone at this point I didn’t know or care, or maybe it was what I really wanted.

“Lynn, baby. You are wonderful and beautiful, and I love what we’ve done, but I need to fuck you.”

“Do it, Matt. Do it.”

Matt set me down on his bed on my hands and knees and pulled down my panties. My cock, which had been ignored for so long sprang to attention, but Matt was interested in other things. He took off his pants and shirt and got in bed behind me. He reached into a drawer in the table beside the bed and got a tube of lube.

Matt rubbed lube over his prick, then onto a finger which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able to move it pretty freely after a minute or two. He snuck a second finger in and began to finger fuck my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the back of my neck as he pulled his fingers out of my ass.

I felt the head of his cock at my asshole and tensed for just a second before relaxing. At this point, I think I wanted him as much as he wanted me. I felt the head get just inside me and I sighed and moved my ass back, getting more of him in me. It hurt a bit, but Matt took it easy and slow at first, until I really started to get into it.

I soon felt his hips slapping up against my ass as he fucked me. If you had told me beforehand that I’d enjoy having a guy fuck my ass, I’d have thought you were crazy and told you to leave me the fuck alone. Now Matt was fucking me and I was in heaven. I felt his cock slide deep in me and fill me up. It turned me on in ways I’d never have expected.

Matt slid his dick in me so far, I could almost feel him jab my stomach. I’d almost swear I saw my tummy bulge as he got all the way in. In spite of whatever reservations I’d had, I was loving every second of this, every stroke of his cock. I wanted his dick in my ass, and when he came with a gush in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our sides, with his prick still inside me. I was on a sexual high and wanted nothing more than to keep feeling his cock in my ass. His dick was getting softer, but I wanted to keep him in me as long as I could. As we came off our high, Matt began to stroke my shoulders and kiss the back and side of my neck.

“Lynn, baby, you are beautiful, sexy, and wonderful, and I just wish I could stay inside you forever.”

“I wish you could stay inside me forever too. I’m yours whenever you want.”

“I just might hold you to that, Lynn, baby.”

Essentially, Matt was spooning me as we lay there in his bed with his cock slowly easing its way out of me. I moved my ass back, trying to keep as much of him in me for as long as I could, as we drifted off to sleep.


I woke the next morning with Matt still spooning me and with his hard cock pressing up against my ass. Something had changed. If I’d woken up yesterday with a guy’s hard dick against my ass, I’d have leapt from bed and gotten out of the room as fast as I could. Instead, I moaned and moved my ass around against his prick.

Matt woke up and began stroking me and kissing the back of my neck as he eased around so his prick was up against my bunghole. I could feel it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our sides. It was a gentler fucking, instead of the pounding that we had at the end last night, but I still loved it.

My dick got hard as I felt his filling me up. It was a slow leisurely fuck, almost loving, and I reached behind me to stroke Matt’s body as he fucked me. He pressed tight against me as he came deep in my ass. I couldn’t believe how much I enjoyed having this guy fuck me, but I knew I wanted it to continue as long as he wanted me.

“Lynn, baby, thank you for last night, and for this morning too.”

“I hope we’ll have more than just last night and this morning.”

“If that’s what you want, we don’t have to stop with one date.”

“I want it. I want your cock in my ass, in my mouth, wherever you want, and whenever you want.”

“I want Lynn. I don’t want Lenny.”

“I never thought I would, but for you, I’ll be Lynn.”

“What happens to Lenny?”

“Lenny has a job, and I don’t think they’d appreciate Lynn showing up in place of Lenny. I need to be Lenny at work.”

By then, Matt’s dick had slipped out of my ass and I’d rolled over facing Matt. I kissed Matt, and he kissed me back and began stroking my body. We spent a long time kissing and touching each other before we got up and went to the shower together. Without my clothes, my bra, my panties, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his cock, I got down on my knees and sucked him off again. With my makeup off and hair wet, I didn’t look quite the same, but I dried my hair, styled it as best I could and got dressed in my clothes from last night. I had a little makeup in my purse and could do lipstick, eyeliner and a little base, to make me more like Lynn.

The more I looked like Lynn, the more Matt seemed to be affectionate. He fucked me once more before taking me home, and we made a date for that evening.

When I got home, I looked at myself in the mirror, then just slumped onto the couch and shook my head. I could feel Matt’s cum leaking out of my ass as I sat there. Who was I? Was I Len or Lynn? Who did I want to be? I wasn’t sure, but guessed I’d have to work it out along the way. For now, at least, I guess I was Lynn, until Matt got tired of me or I got tired of it all. I guess Karen’s extra clothes were now Lynn’s clothes till further notice.

Matt took me out again Saturday night, and took me back to his place. We were not as tired or drunk and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to sleep, I was starting to feel conflicted. Was this really how I wanted to live out my life? And how long was Matt likely to be interested in me?

We fucked a couple more times the next morning and I went home. I decided that Lynn would only be on Friday and Saturday nights. I was going to live and work as Lenny, the rest of the time. It was hard. We all want to be appreciated. We all want someone to think we are special. Lenny isn’t special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as Matt’s wingman. Matt always found an attractive woman to take home. I was a little jealous – both of Matt and of the woman. On rare occasions, I’d be Lynn during the week, and Matt would come to my place to fuck me. Usually Lynn was a weekend thing, but some weekends, Matt had other plans.


One Friday night, Matt and I were at a club and I was being Lynn, though Matt seemed to be giving most of his attention to a very pretty blonde. I sat there feeling pretty neglected, when Nicole came up to talk to me. Nicole was a brunette, about my age, a bit taller, but with a very nice shape, b-cup boobs, and a pretty face.

“Well, honey, your date seems to be ignoring you.”

“I guess I’m old news.”

“Foolish guy. If you were mine, I wouldn’t dump you like that. By the way, my name’s Nicole.”

“Hi, Nicole. I’m Lynn. And Matt and I have kind of an unusual relationship.”

“Well, your guy appears to be about ready to step out with another woman. Would you have any interest in doing the same? Or are you strictly into guys?”

“You mean… you’re interested in women?”

“I like women. I like men. And sometimes I straddle the line.”

“What do you mean by straddling the line, Nicole?”

Nicole reached up, and stroked my face. I’d shaved as cleanly as I could before going out with Matt, and my facial hair is not thick, but there was the slightest trace of very light stubble and I could tell by her expression that she felt it. Nicole leaned forward and kissed me.

“Well, Lynn, something tells me that you straddle the line.”

“And you like that?”

“Let’s dance a bit, honey. After all, your guy seems to be diverted elsewhere. Unless, of course you’re not into women.”

“I like women, I’m just…”

Nicole took my hand and led me out onto the dance floor. I glanced back at Matt and he was so fixated on the blonde that he never even noticed that I left. We did a couple of fast dances, and I really enjoyed dancing with Nicole. Hell, as Lenny, I had trouble getting women to even dance much with me.

A slow number came on and Nicole grabbed me and pulled me close. She put one hand in the middle of my back and the other one down over my ass. I giggled and squirmed as she caressed my ass through the dance. I glanced around and no one seemed to even notice us or what we were doing.

At the end of the dance, Nicole gave me a kiss that almost buckled my knees. I could feel my dick getting harder and barely being restrained by my panties. My mind was blown. We stood there kissing for I’m not even sure how long. I’d never had a woman kiss me like that before, and I was in no hurry for it to end.

We went back to get a drink, and Matt appeared to be gone, as did the blonde he’d been flirting with. It bothered me, but at the same time, it didn’t bother me that much. I wasn’t sure that I wanted a long term relationship with Matt, and he seemed to still be pretty much sleeping around. Besides, now Nicole seemed to be interested in me, or at least I hoped she was.

“Well, Lynn honey, it looks like you lost your guy.”

“Well, I guess I don’t mind, at least as long as I have you for company.”

“Are you sure that’s what you want, Lynn?”

I leaned forward and kissed Nicole, and she returned my kiss. We finished our drinks, danced a bit more then Nicole invited me back to her place. Nicole was an inside sales rep for a tech company. She worked near where I did and made some decent money. I was still amazed that she had any interest in the likes of me.

“Are you sure that’s what you want, Nicole?”

“I know your appearance belies what you have down below, but I’m good with that. As long as you like girls, I think we can have some fun.”

“I like girls, I just never had much luck before.”

“So maybe you never met the right girl before. As long as you’re open minded and flexible, I think we can have lots of fun.”

I felt a little uncertain. Nicole was pretty and she seemed willing. I just didn’t understand why she’d have any interest in me – not after knowing that I was a guy dressed as a girl who’d been out with a guy. Look, I’d never had any woman willing to give me the time of day, much less get intimate with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

Matt had left me and gone off. I could either call an Uber or find out what Nicole had in mind. Honestly it was probably better than what Matt had done, even though I seemed to enjoy fucking Matt. I sat for several seconds, just pondering the possibilities. I looked at Nicole who sat there with a little enigmatic smile on her face, then I leaned forward and kissed her.

“I take it that’s a ‘yes’, then.”

“Why not? If I’m walking on the wild side anyhow, why not walk a little farther?”

“That’s my girl.”

Nicole kissed me, then wrapped an arm around me and we walked out of the club. She had a car nearby, nothing as expensive or flashy as Matt’s BMW, but a Nissan 370Z a couple of years old. It was certainly nicer than my eight year old Civic. Nicole opened the car door for me, which surprised me a bit. Yes, Matt had been doing the same, but Nicole was a woman and knew what I was down below.

I stood slightly puzzled for a second before smiling at her and sitting down in a ladylike fashion. Before she closed the car door, Nicole leaned over and kissed me. She came around, sat down in the driver’s seat and started the car. Before she put it in gear, she smiled at me again and gave me a quick kiss.

“We’ll go to my place, Lynn, unless you have an objection.”

“Best offer I’ve had in a long time.”

“Better than your little boyfriend?”

“No question.”

We were stopped, getting ready to exit the parking lot. I leaned over and gave Nicole a kiss. She smiled and stroked my head, before taking us out on the road. She drove us a few miles to her apartment. It was on the second floor and we had to walk a flight of stairs, but we had our arms around each other, giggling and petting each other as we went.

Nicole had a nice little one bedroom place, clearly feminine, with a muted floral sofa and chairs, along with some art prints on the walls. The prints were largely of women and men, along with a few where it wasn’t quite clear if it was male or female. She walked me over and we sat on the sofa, and she put her arm around me.

“So when did you realize that you were Lynn?”

“I really just started dressing up in my sister’s clothes as a turn-on. I told Matt one time when I was drunk and he wanted me to dress up for him.”

“Obviously, you did.”

“He liked the way I looked and wanted to take me out dressed like that.”

“Had you never gone out dressed that way before?”

“Oh my God, no. Even now, the only time I go out this way is with him.”

“But you were into guys?”

“I didn’t think so, until he took me out as Lynn, then took me home and fucked me.”

“Have you been with any other guys than him?”

“Never. Most of the time, I’m Len or Lenny, and I never look at or think about guys.”

“Well, I like Lynn, and I might even like Lenny. How do you feel about that?”

“I’d love that, Nicole.”

“And if I want you to be Lynn for me, at least some of the time?”

“I’d do that, if that’s what you want.”

“What about your little boyfriend Matt?”

“I think he’s getting a little tired of me.”

“What if he isn’t?”

“I think I’d rather be with you anyhow.”

“Well, Lynn, let’s see how you feel about that later tonight or tomorrow morning.”

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the longest time. I wanted more of course, but I didn’t want to rush things and upset her and maybe make her send me on my way. Nicole stroked my body, mostly back, arms, and ass, so I followed her lead and did the same to her. After a long stretch of kissing and touching, Nicole stopped.

“Lynn, would you unbutton my blouse, please?”

I was more than happy to do so, though my hands were shaking as I began to undo the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her skirt, and she asked me to pull it loose and take it off her. She sat there with only her bra on the upper half of her body. I hardly even noticed as she took my blouse off me.

Nicole took one of my hands and placed it on her breast over her bra. I think my eyes must have gotten very wide. She smiled, then leaned forward and kissed me as I held her boob. I wasn’t sure where she was setting limits, but I couldn’t help but rub her boob through her bra. Nicole moaned and continued to kiss me.

My bra, of course, was filled with padding, not boobs, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the padding, it still sent a shiver of pleasure through my body. She had both hands on what would have been my boobs, if I had any, so I placed my other hand on her other breast.

I was a little concerned about pushing it too far, but Nicole seemed to get even more turned on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the ones I wore for some time, but never messed with anyone else’s bra. I reached behind her and fumbled a bit before getting it unhooked.

I rubbed her back where the bra had been, and Nicole moaned and squirmed, then shrugged, which let the bra fall forward. She had her arms around me, as I had mine around her, so the bra didn’t fall off. She reached behind me and unhooked my bra. We continued to kiss for a while before she leaned back to allow our bras to fall off each of us.

My bra and padding fell to the floor, leaving my bare chest out there. I got my first look at Nicole’s breasts – actually the first breasts I’d ever seen live and in person. I wanted to touch them but I was hesitant. I didn’t want to move too fast and spoil things. Again Nicole put my hand on one of her boobs, then began to stroke my flat, boobless, chest.

Her boobs felt amazing, warm, soft, and just so wonderful. I began to caress her boobs and nipples as Nicole played with my chest. After a little while, she stopped kissing me and guided my mouth down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the breast right on her nipple.

Nicole leaned back, pulling me with her as I began to kiss and lick her breast all over. Her nipple got very hard and stood out farther than I realized they even could. Not only was I reveling in this, her breast seemed to revel in my attention. After a bit, she shifted my head over to the other boob, and I began to give it the same attention that I’d been giving its partner.

I spent a long time kissing and pleasing her breasts, before Nicole clutched my head tightly to her as she moaned and writhed on the sofa. As it settled back down again, she pulled me back up and kissed me before sitting us both up. I was afraid that she was indicating that we were done and was going to send me on my way. Instead Nicole stood and pulled me to my feet and led me by the hand into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

“Lynn, baby, unzip my skirt.”

I unzipped her and she let the skirt slide down her body onto the floor. She stepped out of the skirt, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my skirt. My panties were having trouble restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

“Lynn, I’ll please you, but I want you to please me first. Okay?”

“Anything you want, Nicole.”

“First, take off my panties.”

I moved down her body and Nicole lifted her hips off the bed. I slid her panties down and once they were clear of her ass, she dropped her hips back to the bed and lifted her feet, letting me take them completely off her. Nicole spread her legs and for the first time I got to see a woman’s pussy. Nicole had shaved most of it, except for a narrow strip just above her labia. Nicole gently pulled my head to her nether regions, though I had no idea what I was supposed to do.

“Okay, baby. Kiss it, lick it, stick that tongue in me.”

Nicole directed me as I ate her out, until she wrapped her legs around my head, almost crushing me, while humping my mouth and moaning. My face was wet with her juices as she released me, then pulled me back up to kiss me. We kissed for a while, until she rolled me over and got on top of me. She lifted up on my hips, so I raised them off the bed, and she pulled off my panties.

I was still in full makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the head of my prick, which was as hard as I’ve ever seen it. Look, I’m no great shakes in that department, but I’ve got about six inches, and it was in its full glory as Nicole slid back up my body.

I could feel my prick, sawing between her thighs, even rubbing across her pussy lips as Nicole writhed around on me. Finally, she lifted her hips, grabbed my prick and guided it into her sweet pussy. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was deep inside her. Once in, she paused a bit, getting us both used to the feel of me being in her.

“So, Lynn, do you think you like this?”

“I want to stay with you like this forever.”

“I don’t think you can keep it up that long, but let’s enjoy what we can.”

Nicole began moving her hips taking my dick nearly out of her, then deeply in again. I was in heaven, and wished it could never end, even if I knew she was right. I’d spent so much time jerking off that I didn’t cum immediately. She continued fucking me and kissing me as I played with her boobs and fondled her ass. After a while, I realized I was getting close.

“I’m going to cum, Nicole.”

“Do it baby, right inside me. Fill me up with it.”

As I started to cum, I grabbed her ass and held her tight and as close to me as I could. I filled her with my cum until I had no more to give. I let go of her and just slumped back on the bed. Nicole leaned forward and kissed me sweetly.

“I know that isn’t quite what your boyfriend would do to you, but I hope you enjoyed it anyhow, Lynn.”

“That was wonderful. Better than anything I’ve ever done with Matt.”

“We don’t want you to miss out on anything though.”

“What do you mean.”

Nicole got off me, got up and walked over and opened a drawer. She pulled out something that looked like a penis, but with straps. She came back over to the bed and strapped it on herself, so it now appeared that she had a dick. She had me get on hands and knees, then got some lube from a nearby drawer, before lubing up the penis and my ass.

Nicole eased the thing into my ass, until I was comfortable with it, then began to slowly fuck my ass with this strap-on. I wasn’t sure I wanted her to do that, but at this point, I wasn’t going to argue with her. As she began fucking me, I began to get into it. For obvious reasons, she was able to keep going a lot longer than Matt even could, and my cock got hard again, and I came on the bed.

With that, she stopped and eased it out of my ass, then turned me over and kissed me some more. She kept the device on her even through that. We kissed for a long time before she turned me on my side and spooned me, with her strap-on pressing up against my ass. We fell asleep that way and I had the most contented sleep that I’ve had in ages.


We woke up in the morning, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me fuck her pussy. We showered together, playing as we washed each other. I went down on her in the shower and she went down on me after.

“So, did you have any plans for tonight, Lynn?”

“Nothing specific, but I’d love to spend it with you, if you’re available.”

“That sounds great. I’ve got some errands and things to do this afternoon, so you need to get your cute little ass home, and I’ll see Lynn back here at seven.”

“You’d rather be with me as Lynn than Lenny?”

“For now. Do you have a problem with that?”

“Not as long as I can spend my time with you.”

“That’s my girl. Now get dressed and scoot.”

I put my clothes back on. All I had was Lynn clothes, so I wore those and did my makeup before I left. I got back to my apartment and sat on the sofa, just amazed at the last 24 hours. While I sat there, my phone rang – a call from Matt.

“Hey, babe. Sorry I left you last night, but Toni wanted to get out of there and you seemed all tied up with that brunette you were dancing with.”

“That was Nicole. We were enjoying ourselves.”

“I figured either she’d give you a lift home or you’d catch an Uber or something.”

“Actually, she took me back to her place, and I spent the night there.”

“So she was cool with Lynn and what Lynn was?”

“Yeah, she was.”

“So, Lynn, I was thinking that tonight…”

“Tonight, Nicole and I are going out again. Besides, you have Toni to go play with.”

“You’re hotter than Toni.”

“Maybe you should have thought of that before dumping me for her.”

“Come on, girl. If it weren’t for me, you’d have had no sex life and no chance at that Nicole.”

“But I have Nicole now, and I really like being with her.”

“There are things I can do to you that she can’t, unless she’s like you.”

“She’s all girl, but she’s got devices. I’m not missing out on anything, and I’m getting things I could never get with you. I get to play with boobs, I get to fuck a pussy.”

“Are you fucking dumping me, bitch?”

“Matt, you’ve been a good friend, but I think we both need a change.”

“Lynn, how long do you think that bitch will go before she dumps you?”

“Don’t know, but I’m going to run with this for as long as I can.”

“I give it two weeks at the outside.”

“Well then, I’ll take that two weeks. In the meantime, you have Toni or one of the other many women who fall all over themselves to be with you.”

“Don’t think I’ll forget this.”

“Just remember, if you out me as a cross dresser, you also out yourself as fucking a guy who cross dresses. Your little girlfriends might not take that very well.”

“You know that everything you’ve got with this Nicole, you owe to me.”

“And you’ve gotten payment for that. And if or when Nicole dumps me, if you aren’t too big a bitch, you might even get more. In the meantime, I hope you have a great evening.”

So who was I? Who did I want to be? Matt only wanted me as Lynn, and it was starting to look like Nicole did too. The difference was that I got more out of it with Nicole. It wasn’t just me being fucked, I got a chance to get mine too. Fact is, given a choice, I’d rather be with Nicole or some other woman than to be with Matt.

I guessed I was bisexual enough to get off on what I did with Matt, but why give up on women if I had any chance with them? I was still sitting there in clothes as Lynn, when there was a knock on the door. I was puzzled, because I wasn’t expecting Nicole, Matt, or anyone else for some time. I was a little leery of opening the door, when it was unlocked from outside.

I sat there shocked as my sister Karen came in the apartment. She didn’t spot me immediately, but turned to close and lock the door. She saw me and her mouth hung open and she seemed frozen in place until she began moving slowly toward me. Karen got over to me, reached out a hand and touched my face.

“Lenny? What the fuck?”

“Karen, I’m not quite sure how to explain this.”

Karen sat down beside me on the sofa, looking at me, then gingerly reaching out to touch what I was wearing.

“You’re obviously in my clothes.”

“Yes. It’s kind of a long story.”

“Are you wearing my panties and bras too?”

“I am.”

“I got a bigger place and was going to pick up the rest of my clothes, but if you’ve been wearing them, I don’t think I want them anymore.”

“I’m sorry. I’ll pay you back, or buy you more stuff.”

“So is dressing like this what makes you happy?”

“Not especially, but it makes the girl I spent the night with happy.”

“A girl? A real girl? Not some in between or fake thing?”

“Nicole is a real woman. For some reason she gets off on being with me like this.”

“Could be worse. You could be dressing like that and fucking guys.”

I looked at my shoes. I couldn’t look Karen in the face. She understood immediately.

“Fuck. You mean you did that too?”

“As long as I have Nicole, I don’t want or need any guys.”

“But if she dumps you and you can’t find another woman, you’ll go back to fucking guys?”

“Karen, please.”

“Lenny, it’s your life. Fuck who you want. Just don’t show up at home or my place dressed like that.”

I was crying by this time. Karen made me ashamed of what I’d done and what I’d become. At the same time, I needed love too, and if being Lynn was what kept Nicole then I was going to continue to be Lynn. I wept on Karen’s shoulder, and she took some pity on me and stroked my head and tried to soothe me. It took a while before I regained my composure.

“The real bitch is that you look better in those clothes than I did, Lenny.”

“I hope you can understand and forgive me.”

“I forgive you, and I guess I understand that you’ll do whatever you have to do in order to get off.”

“You were always popular with the guys. I could never get any of the girls to give me a second look.”

“So you dressed this way to get guys?”

“I just dressed like this to get myself off, until a guy I knew saw me. He liked what he saw, and while I wasn’t completely comfortable, it was better than being alone.”

“And this girl you’re with now?”

“Saw me, liked me, and figured out what I was. She liked women and men and seemed happy with me dressed like this.”

“Well, I guess I should be happy for you, even if I’m not thrilled about how you got there.”

“I don’t know how long it’ll last, but I’ll do what I have to do to keep it going.”

“Should I still call you Lenny?”

“When I’m like this, I’m go by Lynn.”

“Well, Lynn, I wish you well with your girlfriend. And I’m not going to wear any of the clothes I left here, so they’re all yours.”

Karen left, and I went in the bathroom to fix my makeup and then changed clothes. I’m not sure where the relationship with Nicole will take me, but I guess time will tell.