Lynn Comes Out

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 she 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. Luckily, 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 she 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."