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 babe, Karen who was a few eld senior than me. She'd had a filthy 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 squeamish little Brother, I let her have the bed, while I slept on the sofa. She had a ton of clothes and Thomas More than filled my cupboard, leaving piffling way for my clothes. Beyond that, we had to share one tiny can, in teddy, since there was no way we were going to be in there at the Lapp time - too small and too weird.

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

Karen left behind all manner of matter, skirts, dresses, blouses, bras, panties, shoes, makeup, and all that. After I while I got fascinated with it, which I supposition was my first misapprehension. I started by just touching some of the wearing apparel. 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 apparel 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 fourth dimension, 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 wearing apparel 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-stimulation 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 constitution she'd left behind. I'd pad her bandeau with wind sleeve or whatever, put on panties, a skirt, blouse, and skid, then sweep my tomentum in a more feminine stylus and learned how to do my makeup.

It all seemed innocuous. I was in my position, by myself, using it all as role of self-abuse. perdition, I needed to get off too, and there were no girls will to help me. Before longsighted, I'd come home base from workplace, dress up all girly, and swagger around my flat before getting myself off. I'd even wear one of Karen's old night-robe to bed afterward.

I had a few friends who I'd hang out with occasionally. One of them, who I'd known since high gear schooltime was Matt. He was always the popular kind, never had any job getting girls, and often seemed to have one or Thomas More hanging off him. He'd train me along as a wingman sometimes, though I never managed to get any girls out of it.

One dark 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 dame to let him thumb her in public in a restaurant. He said they'd also gone to a movie theater, sat way in vertebral column, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.

"Hey, Lenny, what's the far-out matter you've even done ?"

"diddly-squat, flatness, I can't get young woman to do ordinary shit with me, much less anything kinky."

"seed on, guy, you must sustain done something just a trivial bit out there."

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

"Seriously, Len. Do you just slip on her pantie to get turned on or do something to a greater extent ?"

"Sometimes I'll go fully drag, clothes, brake shoe, 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 take someone see me."

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

"matte, 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 tardily and I was too fuddle and had to make the side by side 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 clip to get ready.

"Lenny, do you recollect you can be ready in an minute ?"

"I think so. I get home about six, so come by my berth around seven."

…………………………………………………………………………

The next day I really had some declination 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 border all good afternoon. I got home about six and took off all my apparel. 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 intellection of having this guy see me in my sister's apparel. I dried my haircloth and styled it girlish, then put on panties, a bra, a decent skirt, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on cornerstone, then some accents, eyeliner, eye shadow, lipstick, and of track I painted my toenails and fingernails.

I wore some low heels with open toes, to demo off the toenail Polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly recount when I looked in the mirror. I was still shaking and skittish when the doorbell rang at seven o'clock. My knee joint were wobbly as I walked to the room access. I looked through the peephole and surely enough it was Matt. I opened the threshold and let him in.

lustrelessness was gaping and staring as he walked in my place. I closed and locked the doorway and he turned me around then stepped back to take a full 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 unquiet. He came back in front of me and grabbed me gently by the shoulders.

"shit, 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, mat. I'm not one of your petty girl, 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."

mat 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 shoulder joint and seemed to be getting way too much joy out of this.

"Lynn, baby, you are one hot fox."

"lustrelessness, this tactile property really weird."

"Not weird, Lynn, just a short kinky, baby."

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

"You shouldn't be uncomfortable. You look rattling, one of the aphrodisiac female child I've seen in a while."

"You've got lots of miss - real girls, not counterfeit ones, like me."

"Don't deplumate yourself down. virtually of those young lady have naught on you."

"Jeez, now you're really embarrassing me."

"Let me fill you out to dinner, Lynn"

"Just let me commute 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 person 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 puff ?"

"No one but you and I will recognize, and besides I like a trivial bit of kinky sometimes."

"I don't know."

"Come on, Lynn. A overnice dinner, and I'll kickshaw you the way a madam should be treated."

"That makes me feel really weird."

"And maybe a small turned on ?"

"I don't know if we should be doing this."

"I do, and we should."

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

"Do you need a pocketbook, keys, and such ?"

"I think Karen left a duo of handbag 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. mat 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 intellect why about of the girls fell all over each other to get to him. We went downstairs to his mark new risque BMW Z4 convertible and he opened the door of the car for me. I managed to sit down in a somewhat ladylike mode - I don't think I showed too often. He got in and drove us to a very prissy restaurant.

He used valet de chambre parking and walked me in, holding the door for me. I still felt Wyrd as diddlysquat, but just tried to ignore how I looked and love myself. Matt ordered a nice bottleful of wine-coloured for us, and I really needed something to tope. I downed my first glass before he'd taken more than a couple sips of his wine. Matt poured me another methamphetamine, but I took it a little slower.

The waiter seemed very taken with me, and when he thought I didn't notification, tried looking down my blouse. several other men seemed to point out me, which made me squirm in my buns. One guy who works with matt stopped at the table to lecture with us. I'd met him several times before, but he clearly didn't spot me.

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

"This is my day of the month, Lynn. Lynn, sports meeting Oliver, he ‘ s another department manager where I work."

"I'm so pleased to adjoin you, Oliver."

"And I'm very pleased to gather you, Lynn. lustrelessness is clearly a very favourable man. But if you want a alteration of scenery, give me a call, I'd love to show you a good time."

With that, King 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."

"fountainhead, Matt, if you get tired of Lynn here, feel free to station her my way."

Oliver bent down and kissed my nerve 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 knock down their date for a chance to train you home."

"That's only because they don't know what I really am."

We had a lovely dinner party and I continued to wassail way more than than I should have. This whole scene had blown my mind so a great deal I didn't know what else to do. A few early men stopped to mouth to us. They invariably seemed to pay inordinate tending to me, when they stopped to talk to Matt. We finished dinner and I thought lustrelessness would take me back to my place.

"Lynn, love, it's still early, why don't we go dancing ?"

"Are you sure about that ?"

"You're taking a walk on the wild incline, just read a bit longer walk."

Matt wouldn't take ‘ no'for an answer and beat back us to the hot club in townsfolk. This was the sort of place that would never let the ilk of me inside. They must have had a hundred the great unwashed 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 swallow and then matt wanted to trip the light fantastic toe with me. I felt strange as bullshit, but it was a quick number and I was already half plastered so I went out to dance with him. We danced several firm dances, then a tedious number came on. I thought we'd go sit down, but instead, Matt pulled me close to him to dance.

He had one paw on my pep pill back, holding me tight, as his former handwriting came down on my ass. He began to fondle my ass, which made me wriggle. I could find that mat 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 fuddled, and kissed me.

My genu got so decrepit that if he hadn't been holding me close, I'd probably have slumped onto the floor. He gave me a yearn osculation, and to my surprise, I began to buss him back. I felt infringe - 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 swallow.

I'd been drinking pretty ripe 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 - lustrelessness 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 flatness's wingman more than a few times, and had seen him this way with woman many times before. I also knew that in most sheath he ended up taking those adult female nursing home and fucking them. That scared me, but also seemed to wrick me on, and it scared me that I was turned on by it. I don't bonk how long we danced and drank, but by the time Matt was make to leave, I was really plastered.

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

"Matt, I really need to get home and change."

"Lynn, beloved, there's no hurry. Just relax and enjoy your manner of walking on the uncivilized side."

Matt got us each a drink, like I needed any more inebriant, and sat me down on the lounge, sitting right-hand alongside me. lusterlessness put his arm around me and pulled me tight, then began to buss me. He started just with the lips, then added in some tongue, while feeling up my ass and my impostor 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 prepare 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 experience effective 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."

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

Matt moaned and leaned back, still keeping a hand on my head. I let the psyche 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 son of a bitch, gradually taking it abstruse and mysterious into my mouth. I'd never had a putz in my mouthpiece before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my mouth and lustrelessness 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 coxa, almost fucking my rima oris, as he held my head tight.

Matt moaned loudly and got very fixed as his cock erupted in my sassing. He held my head with both hands as he emptied his bollock into my pharynx. I swallowed his cum and gasped for breathing space, 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.

mat pulled me up on him and began to kiss me some more. I know he had to smack his own cum in my oral fissure as we kissed, but that didn't seem to inconvenience him. Matt continued to snog 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 panty. He even snuck his paw into my pantie and fondled my bare ass.

I don't know why I didn't placard, 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 power 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 make out you."

"Do it, flatness. Do it."

mat set me down on his bed on my mitt and knee joint and pulled down my panties. My cock, which had been ignored for so foresighted sprang to attending, 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 thermionic valve of lube.

Matt rubbed lubricator 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-bodied to affect it pretty freely after a minute or two. He snuck a 2d fingerbreadth in and began to finger know my ass, and in spitefulness of myself, I began to be intimate him back. Matt leaned down and kissed the cover of my neck opening as he pulled his fingerbreadth 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 than of him in me. It hurt a bit, but Matt took it leisurely and slack at initiative, 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 unhinged and told you to forget me the fuck alone. Now Matt was fucking me and I was in Shangri-la. I felt his tool chute deep in me and fulfill me up. It turned me on in direction I'd never have expected.

Matt slid his dick in me so far, I could almost experience him jab my stomach. I'd almost swear I saw my tum jut as he got all the way in. In cattiness of whatever reservations I'd had, I was loving every bit of this, every stroke of his dick. I wanted his dick in my ass, and when he came with a outburst 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 school and wanted cypher more than to keep feeling his cock in my ass. His dick was getting balmy, but I wanted to go on him in me as long as I could. As we came off our high, Matt began to stroke my berm and kiss the back and English of my neck.

"Lynn, baby, you are beautiful, aphrodisiacal, and terrific, and I just wish I could stay inside you forever."

"I wish you could rest 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 pecker slowly easing its way out of me. I moved my ass back, trying to keep as a lot of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the following good morning with flatness still spooning me and with his hard shaft pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's heavily dick against my ass, I'd have leapt from bed and take out of the elbow 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 shaft was up against my arsehole. I could feel it and wanted it back inside me. I reached around, grabbed his hammer and guided it into my ass, as we lay on our incline. It was a gentler fuck, instead of the throbbing that we had at the end go Nox, but I still loved it.

My gumshoe got laborious as I felt his pick me up. It was a slow leisurely piece of ass, almost loving, and I reached behind me to stroke mat'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 have it off 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 Sir Thomas More than just live on 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 lip, 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 cock had slipped out of my ass and I'd rolled over face up Matt. I kissed mat, and he kissed me back and began stroking my body. We spent a long time kissing and touching each former before we got up and went to the shower together. Without my wearing apparel, my bra, my panty, I looked more like Lenny, but we washed each other, continuing to kiss.

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

The more I looked like Lynn, the more lusterlessness 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 didder my pass. 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 do work it out along the way. For now, at least, I guess I was Lynn, until lusterlessness got tired of me or I got tired of it all. I surmisal Karen's superfluous dress were now Lynn's clothes till further notice.

flatness took me out again Saturday dark, and took me back to his station. We were not as shopworn or drunk and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to catch some Z's, I was starting to feel infringe. Was this really how I wanted to live out my life ? And how long was lusterlessness likely to be interested in me ?

We fucked a couple more metre the next morning and I went home. I decided that Lynn would only be on Friday and Sabbatum Nox. I was going to populate and work as Lenny, the rest of the time. It was hard. We all want to be appreciated. We all want someone to call back we are special. Lenny is n't special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as flatness 's wingman. Matt always found an attractive char to conduct home. I was a fiddling jealous - both of matte and of the woman. On rarefied occasion, I 'd be Lynn during the week, and Matt would fall to my seat to fuck me. Usually Lynn was a weekend thing, but some weekends, matt had other plans.

... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ..

One Friday dark, 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 reasonably blonde. I sat there feeling pretty neglected, when Nicole came up to speak to me. Nicole was a brunette, about my age, a bit taller, but with a very decent material body, b-cup boobs, and a pretty face.

'' Well, honey, your engagement seems to be ignoring you. ``

'' I guess I 'm old news. ``

'' Foolish guy. If you were mine, I would n't dump you like that. By the way, my name 's Nicole. ``

'' Hi, Nicole. I 'm Lynn. And flatness and I have kind of an unusual family relationship. ``

'' Well, your guy appears to be about prepare to step out with another womanhood. Would you have any interest in doing the Saame ? Or are you strictly into guys ? ``

'' You mean ... you 're occupy in woman ? ``

'' I like women. I like men. And sometimes I straddle the line. ``

'' What do you think of by straddling the line of work, Nicole ? ``

Nicole reached up, and stroked my facial expression. I 'd shaved as cleanly as I could before going out with lusterlessness, and my facial hair's-breadth is not thickly, but there was the fragile trace of very light stubble and I could say by her expression that she felt it. Nicole leaned forward and kissed me.

'' wellspring, Lynn, something Tell me that you straddle the line. ``

'' And you like that ? ``

'' Let 's dance a bit, dear. After all, your guy seems to be diverted elsewhere. Unless, of course of instruction you 're not into fair sex. ``

'' I like adult female, I 'm just ... ''

Nicole took my hand and led me out onto the dance level. I glanced back at lustrelessness 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 woman to even dance much with me.

A slow issue came on and Nicole grabbed me and pulled me close. She put one hand in the middle of my back and the former 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 remark us or what we were doing.

At the end of the dancing, Nicole gave me a kiss that almost buckled my human knee. I could sense my dick getting harder and barely being restrained by my pantie. 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 deglutition, and matt appeared to be gone, as did the blonde he'd been flirting with. It bothered me, but at the same meter, it didn't bother me that much. I wasn't sure that I wanted a long term human relationship with lustrelessness, 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."

"wellspring, 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 agreement rep for a tech caller. 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 salutary with that. As long as you like girls, I think we can feature some fun."

"I like daughter, I just never had often hazard before."

"So maybe you never met the flop girlfriend before. As long as you're open minded and flexible, I think we can induce 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 pastime in me - not after knowing that I was a guy dressed as a girl who'd been out with a guy. spirit, I'd never had any womanhood willing to give me the prison term of day, much less get intimate with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

flatness had left me and gone off. I could either scream an Uber or find out what Nicole had in judgement. Honestly it was probably practiced than what lustrelessness had done, even though I seemed to enjoy fucking Matt. I sat for several bit, just pondering the possibility. I looked at Nicole who sat there with a niggling enigmatic grinning on her case, 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 take the air a little farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the gild. She had a car nearby, zero as expensive or cheap as Matt's BMW, but a Nissan 370Z a duet of years old. It was certainly nicer than my eight yr old Civic. Nicole opened the car doorway 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 moment before smiling at her and sitting down in a ladylike manner. Before she closed the car doorway, Nicole leaned over and kissed me. She came around, sat down in the driver's nates and started the car. Before she put it in gear, she smiled at me again and gave me a quickly 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 minuscule beau ?"

"No question."

We were stopped, getting cook to exit the parking lot. I leaned over and gave Nicole a candy 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 mo trading floor and we had to take the air a trajectory of stair, but we had our arms around each early, giggling and petting each former as we went.

Nicole had a nice little one bedchamber place, clearly feminine, with a muted floral sofa and professorship, along with some art mark on the paries. The prints were largely of womanhood and men, along with a few where it wasn't quite clean 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 babe's apparel as a turn-on. I told mat one meter when I was drunk and he wanted me to cut back up for him."

"Obviously, you did."

"He liked the way I looked and wanted to admit me out dressed like that."

"Had you never gone out dressed that way before ?"

"Oh my God, no. Even now, the but time I go out this way is with him."

"But you were into guy ?"

"I didn't think so, until he took me out as Lynn, then took me place and fucked me."

"Have you been with any other Guy than him ?"

"Never. almost of the clock time, I'm Len or Lenny, and I never look at or think about guys."

"wellspring, I like Lynn, and I might even wish 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 metre ?"

"I'd do that, if that's what you want."

"What about your fiddling boyfriend Matt ?"

"I think he's getting a piddling bore of me."

"What if he isn't ?"

"I think I'd rather be with you anyhow."

"wellspring, Lynn, let's see how you feel about that tardy tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the long fourth dimension. I wanted more of course, but I didn't want to rush matter and upset her and maybe make her send me on my way. Nicole stroked my body, mostly back, weaponry, and ass, so I followed her lead and did the Sami to her. After a long reaching of kissing and touching, Nicole stopped.

"Lynn, would you unbutton my blouse, please ?"

I was more than happy to do so, though my manpower 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 rip it loose and take it off her. She sat there with only her bra on the upper half of her trunk. I hardly even noticed as she took my blouse off me.

Nicole took one of my hands and placed it on her titty over her bra. I think my optic must have gotten very across-the-board. She smiled, then leaned forward and kissed me as I held her breast. I wasn't sure where she was setting demarcation, but I couldn't assistant but rub her dumbbell through her bra. Nicole moaned and continued to kiss me.

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

I was a niggling concerned about pushing it too far, but Nicole seemed to get even more work on. We continued like this for a spell before she asked me to unhook her bra. I had been fastening and unfastening the unity 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 weapons system 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 bra to settle off each of us.

My bra and padding fell to the floor, leaving my bare thorax out there. I got my first look at Nicole's breasts - actually the first white meat I'd ever seen experience and in person. I wanted to touch them but I was hesitating. I didn't want to go too fast and frustrate things. Again Nicole put my script on one of her knocker, then began to stroke my flat, boobless, chest.

Her tit felt puzzle, affectionate, cushy, and just so wonderful. I began to caress her boob and nipples as Nicole played with my chest of drawers. After a little while, she stopped kissing me and guided my mouth down to one of her delightful boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the breast rightfulness on her nipple.

Nicole leaned back, pulling me with her as I began to buss and lick her boob 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 make whoopie in my tending. After a bit, she shifted my head over to the other boob, and I began to give it the Sami tending that I'd been giving its partner.

I spent a farsighted metre fondling and pleasing her breasts, before Nicole clutched my heading 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 bird slide down her organic structure 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 dapple in the forepart of them, as Nicole unzipped my bird. My scanty were having hassle restraining my pecker, 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, consider off my panties."

I moved down her body and Nicole lifted her hips off the bed. I slid her scanty down and once they were clear of her ass, she dropped her hips back to the bed and lifted her feet, letting me get them completely off her. Nicole spread her pegleg and for the offset fourth dimension I got to see a woman's puss. Nicole had shaved most of it, except for a narrow cartoon strip just above her labia. Nicole gently pulled my head teacher to her under regions, though I had no melodic theme what I was supposed to do.

"Okay, child. 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 human face was wet with her juices as she released me, then pulled me back up to kiss me. We kissed for a spell, until she rolled me over and got on top of me. She lifted up on my rose hip, so I raised them off the bed, and she pulled off my panties.

I was still in full make-up as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the pass of my prick, which was as laborious as I've ever seen it. Look, I'm no great shiver in that department, but I've got about six inches, and it was in its total resplendency as Nicole slid back up my body.

I could palpate my bastard, sawing between her thighs, even rubbing across her pussy lips as Nicole writhed around on me. Finally, she lifted her rosehip, grabbed my putz and guided it into her sweet kitty-cat. 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 flavor of me being in her.

"So, Lynn, do you cerebrate you like this ?"

"I want to stay with you like this forever."

"I don't think you can prevent it up that long, but let's enjoy what we can."

Nicole began moving her coxa taking my shaft 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 a great deal sentence 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 patch, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it indulge, the right way 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 devote. 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 beau would do to you, but I hope you enjoyed it anyhow, Lynn."

"That was marvelous. 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 putz. She had me get on work force and knees, then got some lubricating substance from a nearby drawer, before lubing up the member and my ass.

Nicole eased the matter into my ass, until I was comfortable with it, then began to slowly eff 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 debate with her. As she began fucking me, I began to get into it. For obvious intellect, she was able to keep going a lot retentive than Matt even could, and my peter 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 retentive time before she turned me on my side of meat 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 bed 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 plan for tonight, Lynn ?"

"Nothing specific, but I'd love to drop it with you, if you're available."

"That sounds great. I've got some errands and things to do this good 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 pass 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 composition before I left. I got back to my apartment and sat on the couch, just amazed at the finally 24 hr. While I sat there, my telephone rang - a call from Matt.

"Hey, infant. 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 contribute 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 bring with."

"You're blistering than Toni."

"Maybe you should receive thought of that before dumping me for her."

"seminal fluid on, young lady. 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 matter I can do to you that she can't, unless she's like you."

"She's all girlfriend, but she's got twist. 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 longsighted 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 early 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 chest of drawers, you also out yourself as fucking a guy who cross garb. Your fiddling girlfriends might not take that very well."

"You know that everything you've got with this Nicole, you owe to me."

"And you've become payment for that. And if or when Nicole knock down me, if you aren't too big a bitch, you might even get to a greater extent. In the interim, 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 departure 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 former woman than to be with Matt.

I guessed I was bisexual enough to get off on what I did with flatness, but why give up on women if I had any opportunity 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 picayune 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 interlock the door. She saw me and her mouth hung unresolved and she seemed immobilise in place until she began moving slowly toward me. Karenic got over to me, reached out a hand and touched my face.

"Lenny ? What the fuck ?"

"Karenic, I'm not quite sure how to explicate this."

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

"You're obviously in my clothes."

"Yes. It's sort of a prospicient 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 glad ?"

"Not especially, but it makes the daughter I spent the dark with happy."

"A girl ? A real young lady ? Not some in between or fake thing ?"

"Nicole is a actual woman. For some reason she gets off on being with me like this."

"Could be sorry. You could be dressing like that and fucking guys."

I looked at my skid. I couldn't look Karenic in the font. She understood immediately.

"piece of ass. 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 cat ?"

"Karen, please."

"Lenny, it's your life. nookie who you want. Just don't display up at home plate 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 Lapplander metre, I needed enjoy too, and if being Lynn was what kept Nicole then I was going to stay on to be Lynn. I wept on Karen's shoulder, and she took some pathos on me and stroked my head teacher and tried to solace me. It took a while before I regained my composure.

"The really beef 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 guy wire ?"

"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 well-off, 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 cleaning lady and men and seemed felicitous with me dressed like this."

"Well, I guess I should be glad for you, even if I'm not thrilled about how you got there."

"I don't make love how yearn it'll last, but I'll do what I have to do to keep it going."

"Should I still call off 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 apparel I left here, so they're all yours."

Karenic left, and I went in the lav to fix my war paint and then changed dress. I'm not sure where the relationship with Nicole will take me, but I guess metre will evidence .