It started form of strange. I am or at least was Len or Lenny - Leonard to my female parent - a guy in my too soon 20s, sort of inadequate and slender. I had a Sister, Karen who was a few eld aged 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 sleeping accommodation topographic point, and not all that big. Being a nice short brother, I let her have the bed, while I slept on the lounge. She had a ton of apparel and more than filled my W.C., leaving niggling way for my clothes. Beyond that, we had to share one tiny bath, in shift key, 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 piazza and moving out. Her place was small than mine, so while she took most of her hooey, 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 shoes until she could afford a full-grown stead. Again, being a nice blood 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 conjecture was my start misunderstanding. 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 wearing apparel while touching myself, then jerking off until I came. I progressed to smelling the dress 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 wearing apparel. That seemed to be a bounteous turn-on and her apparel seemed to fit, since we were almost the same size.

As time went on, I'd raiment up completely in Karen's dress for my self-abuse sessions, and even left them on after I'd cum. I began to take on with it all a fiddling bit and even began to use some of the makeup she'd left behind. I'd pad her bra with socks or whatever, put on panties, a skirt, blouse, and horseshoe, then sweep my hair in a more feminine style and learned how to do my makeup.

It all seemed innocent. I was in my berth, by myself, using it all as part of self-stimulation. hell on earth, I needed to get off too, and there were no girls willing to aid me. Before foresightful, I'd come home from study, enclothe up all girly, and swagger around my flat before getting myself off. I'd even wear one of Karen's old gown 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 to a greater extent than I should have, and we began talking. He started telling me about how he got some bird to let him thumb her in public in a eating house. He said they'd also gone to a moving picture field of operations, sat way in back, and she hiked up her bird, sat on his lap, and fucked him in the theater during the movie.

"Hey, Lenny, what's the kinkiest matter you've even done ?"

"Shit, mat, 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 footling bit out there."

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

"Seriously, Len. Do you just mistake on her scanty to get turned on or do something more ?"

"Sometimes I'll go broad drag, apparel, shoes, makeup, and everything."

"Fuck, man, that I'd like to see."

"I don't know, dude. nonentity 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 go away town."

"Lenny, I swear to God, I'll never tell anyone."

That was Thursday, and it was already latterly and I was too drink in and had to work the succeeding day. He asked if I'd curry up for him the next dark. I agreed and told him to come by after work on Fri, but to give me some sentence to get ready.

"Lenny, do you reckon you can be cook in an 60 minutes ?"

"I think so. I get home about six, so come by my lieu 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 wearing apparel. I swear I was shaking as I cleaned up, showered with scented body lavation, shaved my face, branch, 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 whisker and styled it girlish, then put on pantie, a bra, a nice annulus, and a blouse, then sat down to do composition. By now I had it almost to a skill, putting on base, then some accents, eyeliner, eye shadow, lipstick, and of course of study I painted my toenails and fingernails.

I wore some low heels with undetermined toes, to show off the toenail cultivation 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 spyhole and sure enough it was Matt. I opened the threshold and let him in.

flatness was gaping and staring as he walked in my office. I closed and locked the doorway and he turned me around then stepped back to select a good smell 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.

"hoot, 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 body of work. How about I call you Lynn ?"

"Okay, matte, you got to see me, now let me exchange back."

"handgrip on, Lynn, not so fast. Don't run off on me already. seminal fluid sit on the sofa with me."

"I don't think we should do that, lusterlessness. I'm not one of your little lady friend, I'm Lenny."

"While you're like this, you're Lynn, and I like Lynn. seed on, please sit on the lounge with me."

"This was a mistake. I shouldn't have done this. I want to change."

Matt put and arm around me blotto 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 lots joy out of this.

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

"Matt, this tactile property really weird."

"Not weird, Lynn, just a footling 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 aphrodisiacal girls I've seen in a while."

"You've got batch of girls - genuine girls, not pseudo ones, like me."

"Don't deplumate yourself down. nearly of those girls have nothing on you."

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

"Let me hold you out to dinner, Lynn"

"Just let me modify into some formula clothes, Matt."

"No, babe, just like this."

"God, I can't go out in populace like this."

"Sure you can, baby. You look absolutely stunning."

"What if someone sees me - recognizes me ?"

"No one will greet 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 have sex, and besides I like a little bit of kinky sometimes."

"I don't know."

"Come on, Lynn. A skillful dinner, and I'll treat you the way a noblewoman 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, lusterlessness got up and make me to my animal foot. He wrapped his weapon system around me and pulled me nigh. I think my heart were the sizing of dish aerial and my knees were getting infirm as he leaned forward and kissed me on the impertinence. He let go with one arm and walked me to the threshold. When we got there, he stopped and turned.

"Do you need a purse, Key, and such ?"

"I think Karen left a couple of purses here too."

"snap one and your cay 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. flatness went with me in the bedroom, and I went in the loo 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 certain we should be doing this, Matt."

"Everything is going to be just fine, Lynn."

Matt actually had money, which is yet another ground why about 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 way - I don't think I showed too much. He got in and drove us to a very overnice restaurant.

He used valet parking and walked me in, holding the doorway for me. I still felt weird as Irish bull, but just tried to ignore how I looked and enjoy myself. Matt ordered a skillful bottleful of wine for us, and I really needed something to drink. I downed my low glass before he'd taken more than a twain sips of his wine. Matt poured me another field glass, but I took it a trivial 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 wriggle in my seat. One guy who works with matte stopped at the table to talk with us. I'd met him several sentence before, but he clearly didn't make out me.

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

"This is my engagement, Lynn. Lynn, meet King Oliver, he ‘ s another department managing director where I work."

"I'm so pleased to run across you, Oliver."

"And I'm very pleased to conform to you, Lynn. matt is clearly a very lucky man. But if you want a modification of scenery, turn over me a birdcall, I'd love to indicate you a good time."

With that, King Oliver handed me a line of work 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, lustrelessness, if you get tired of Lynn here, feel free to send her my way."

King Oliver bent down and kissed my brass before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot chick. Half the men in this position would plunge their appointment for a prospect to ingest you home."

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

We had a cover girl dinner party and I continued to drink way more than I should have. This whole aspect 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 party and I thought Matt would claim 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 pass on the uncivilized side, just take a bit longer walk."

lustrelessness wouldn't take ‘ no'for an answer and tug us to the raging cabaret in town. This was the form 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 swallow and then flatness wanted to trip the light fantastic toe with me. I felt unknown as shit, but it was a dissolute number and I was already half plastered so I went out to dance with him. We danced several fast dances, then a dull routine 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 berth back, holding me stringent, as his other hired man came down on my ass. He began to fondle my ass, which made me wriggle. I could feel that flatness had a hard-on as he did that. That scared me more than than a footling, but I wasn't certainly what I could do. I felt helpless as we danced. When the numeral ended, flatness stopped, held me tight, and kissed me.

My genu got so decrepit 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 moment before he walked me back and we had another drunkenness.

I'd been drinking pretty trade good before, but I didn't decelerate down. I was half afraid of what was going to occur, and felt like I needed to be very drink. We drank more and danced to a greater extent, and the more we drank and danced, the Sir Thomas More Matt kept feeling me up and kissing me. My psyche was blown - matte 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 mat's wingman more than a few times, and had seen him this way with char many metre before. I also knew that in most cases he ended up taking those cleaning lady menage and fucking them. That scared me, but also seemed to change by reversal me on, and it scared me that I was turned on by it. I don't fuck how long we danced and drank, but by the time Matt was ready to leave, I was really plastered.

I thought flatness was going to drive me back to my piazza, but instead he drove me to his apartment. As I said, mat had money, and he had a very nice two bedroom apartment - dainty furniture and all that. Part of me hoped that he was going to let me dash in the spare sleeping room. Another voice of me wanted anything but that.

"matt, I really ask to get nursing home and change."

"Lynn, dear, there's no haste. Just relax and enjoy your pass on the wild side."

matt got us each a drink, like I needed any more intoxicant, and sat me down on the couch, 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 sham 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 beneficial prison term. I've made you feel good. You seem to be getting into this. Can't you help me feel dependable too ?"

"What… What did you want me to do ?"

"If nil 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 deal. He pulled out his shaft, which was already hard and standing straight up. He kissed me again, then gently pushed my capitulum down toward his prick. I got unaired and looked at it. It was long and intemperately 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 tool between my lips.

Matt moaned and leaned back, still keeping a hand on my head. I let the foreland of his pecker slipperiness from between my lips, before taking it back and going just a small farther with it. I bobbed up and down on his prick, gradually taking it profoundly and recondite into my mouth. I'd never had a tool 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 preference, 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 pelvis, almost fucking my sassing, as he held my read/write head tight.

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

Matt pulled me up on him and began to snog me some more. I know he had to savor his own cum in my oral cavity as we kissed, but that didn't seem to disoblige him. Matt continued to kiss me and I didn't even realize it as he pulled my wench up over my ass and began to caress my ass through my panties. He even snuck his hand into my pantie and fondled my bare ass.

I don't know why I didn't observance, I don't know why I didn't stop him. Maybe I was enjoying it all too a lot, 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 degree I didn't know or wish, or maybe it was what I really wanted.

"Lynn, sister. You are wonderful and beautiful, and I love what we've done, but I need to have it off 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 mat was interested in former things. He took off his knickers and shirt and got in bed behind me. He reached into a draftsman in the board beside the bed and got a tube of lube.

mat 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 capable to move it pretty freely after a minute of arc or two. He snuck a s finger in and began to finger do it my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the back of my neck opening as he pulled his fingers out of my ass.

I felt the read/write head of his cock at my asshole and tensed for just a second before relaxing. At this gunpoint, I think I wanted him as much as he wanted me. I felt the capitulum get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but lustrelessness took it easy and slow at start, 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 nookie my ass, I'd have thought you were crazy and told you to leave me the shag alone. Now mat was fucking me and I was in Shangri-la. I felt his cock swoop deep in me and satisfy me up. It turned me on in ways I'd never have expected.

Matt slid his dick in me so far, I could almost palpate him jab my tummy. I'd almost swear I saw my potbelly bulge as he got all the way in. In spite of whatever qualification 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 blowup in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our face, with his shaft still inside me. I was on a sexual high and wanted nothing more than to keep feeling his cock in my ass. His tool 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 dorsum 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 view as you to that, Lynn, baby."

Essentially, Matt was spooning me as we lay there in his bed with his dick 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 succeeding morning with Matt still spooning me and with his toilsome 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 elbow room as fast as I could. Instead, I moaned and moved my ass around against his prick.

lustrelessness woke up and began stroking me and kissing the spine of my neck as he eased around so his shit was up against my bunghole. I could finger it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our position. It was a gentler ass, instead of the pounding that we had at the end live nighttime, but I still loved it.

My pecker got grueling as I felt his filling me up. It was a slow leisurely fuck, almost loving, and I reached behind me to stroke lusterlessness's dead 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 be intimate me, but I knew I wanted it to continue as long as he wanted me.

"Lynn, baby, thank you for finish 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, mat's dick had slipped out of my ass and I'd rolled over veneer flatness. I kissed mat, and he kissed me back and began stroking my body. We spent a foresightful time snuggling and touching each other before we got up and went to the rain shower together. Without my apparel, my bra, my panties, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his dick, I got down on my knees and sucked him off again. With my makeup off and hairsbreadth wet, I didn't look quite the Lapplander, but I dried my hair, styled it as Best I could and got dressed in my clothes from cobbler's last night. I had a little composition in my bag and could do lipstick, eyeliner and a picayune base, to pull in 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 dwelling house, 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 finger 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 run 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 venture Karenic's extra clothes were now Lynn's apparel till further notice.

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

We fucked a span more fourth dimension the next forenoon and I went rest home. I decided that Lynn would only be on Friday and Saturday nights. I was going to hold out and mold as Lenny, the rest period of the time. It was hard. We all want to be appreciated. We all want someone to reckon we are special. Lenny is n't especial to anyone, though Lynn is.

Occasionally during the hebdomad, I would be Lenny and go out as matt 's wingman. Matt always found an attractive cleaning lady to take home. I was a little jealous - both of matt and of the woman. On rare affair, I 'd be Lynn during the calendar week, and matt would come to my place to make love me. Usually Lynn was a weekend thing, but some weekends, Matt had former plans.

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

One Friday Night, lustrelessness and I were at a club and I was being Lynn, though matt seemed to be giving almost 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 courteous shape, b-cup tit, and a pretty face.

'' Well, dearest, your date seems to be ignoring you. ``

'' I guess I 'm old newsworthiness. ``

'' dopey guy. If you were mine, I would n't floor you like that. By the way, my gens 's Nicole. ``

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

'' wellspring, your guy appears to be about ready to mistreat out with another adult female. Would you receive any interest in doing the same ? Or are you strictly into guys ? ``

'' You mean ... you 're interested in fair sex ? ``

'' I like woman. I like men. And sometimes I straddle the furrow. ``

'' What do you mean by straddling the line, Nicole ? ``

Nicole reached up, and stroked my aspect. 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 face that she felt it. Nicole leaned forward and kissed me.

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

'' And you like that ? ``

'' Let 's dance a bit, honey. After all, your guy seems to be diverted elsewhere. Unless, of class you 're not into cleaning woman. ``

'' I like women, I 'm just ... ''

Nicole took my bridge player and led me out onto the terpsichore 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 hassle getting char to even out dance much with me.

A slow number came on and Nicole grabbed me and pulled me close. She put one bridge player in the midsection 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 discover us or what we were doing.

At the end of the saltation, Nicole gave me a kiss that almost buckled my knee joint. I could find my dick getting intemperate and barely being restrained by my panty. My psyche 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 haste for it to end.

We went back to get a drinking, and mat appeared to be gone, as did the blonde he'd been flirting with. It bothered me, but at the Sami time, it didn't bother me that much. I wasn't sure that I wanted a long condition relationship with Matt, and he seemed to still be pretty lots 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 head, 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 deglutition, danced a bit more then Nicole invited me back to her place. Nicole was an inside sales rep for a tech companionship. She worked near where I did and made some decent money. I was still amazed that she had any pastime in the the like of me.

"Are you sure that's what you want, Nicole ?"

"I know your visual aspect belies what you have down below, but I'm good with that. As long as you like missy, I think we can birth some fun."

"I like girls, I just never had much circumstances before."

"So maybe you never met the in good order girl before. As long as you're open minded and whippy, I think we can birth lots of fun."

I felt a little unsettled. 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 leave to kick in 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 telephone 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 flatness. I sat for several second base, just pondering the possibility. I looked at Nicole who sat there with a little oracular 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 furious slope 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 ball club. She had a car nearby, nothing as expensive or flashy as lusterlessness's BMW, but a Nisan 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 cleaning lady and knew what I was down below.

I stood slightly puzzled for a 2d 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 number one wood's place and started the car. Before she put it in geared wheel, 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 prospicient time."

"wagerer than your little boyfriend ?"

"No question."

We were stopped, getting ready to pass away the parking lot. I leaned over and gave Nicole a buss. 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 escape of step, but we had our weapons system around each former, giggling and petting each other as we went.

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

"So when did you actualize that you were Lynn ?"

"I really just started dressing up in my sister's clothes as a turn-on. I told matte one prison term when I was drunk and he wanted me to coif 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 clock 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 guys than him ?"

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

"fountainhead, 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 swain 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 previous tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the foresightful time. I wanted Sir Thomas More of course, but I didn't want to bucket along affair and upset her and maybe make her send me on my way. Nicole stroked my organic structure, mostly back, blazon, and ass, so I followed her spark advance 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 work force were shaking as I began to unwrap the clitoris. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her wench, and she asked me to deplume it relax and carry it off her. She sat there with only her bra on the pep pill half of her consistency. I hardly even noticed as she took my blouse off me.

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

My bra, of path, was filled with padding, not goof, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the cushioning, it still sent a chill of pleasure through my dead body. She had both custody on what would sustain been my boobs, if I had any, so I placed my other deal on her early breast.

I was a little bear on about pushing it too far, but Nicole seemed to get even more wrick on. We continued like this for a patch 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 weapon 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 piece before she leaned back to allow our bras to fall off each of us.

My bra and cushioning fell to the floor, leaving my bare breast out there. I got my first face at Nicole's breasts - actually the first of all breasts I'd ever seen springy and in somebody. I wanted to affect them but I was hesitant. I didn't want to locomote too fast and spoil affair. Again Nicole put my manus on one of her boobs, then began to stroke my 2-dimensional, boobless, chest.

Her tit felt flummox, quick, soft, and just so wonderful. I began to caress her dope and nipples as Nicole played with my bureau. After a short spell, she stopped kissing me and guided my mouth down to one of her delicious knocker. I looked up at her, and she smiled at me, so I moved forward and kissed the breast right field on her nipple.

Nicole leaned back, pulling me with her as I began to snog and lap 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 chest seemed to make whoopie in my attending. After a bit, she shifted my question over to the other boob, and I began to turn over it the Lapplander attention that I'd been giving its partner.

I spent a long time kissing and pleasing her breasts, before Nicole clutched my drumhead 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 foot and led me by the paw into her chamber. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, infant, unzip my skirt."

I unzipped her and she let the wench slide down her body onto the flooring. She stepped out of the skirt, then kicked off her skid. She now wore only pantie, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my bird. 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 delight me first. Okay ?"

"Anything you want, Nicole."

"kickoff, contain off my panties."

I moved down her body and Nicole lifted her articulatio coxae off the bed. I slid her scanty down and once they were realize of her ass, she dropped her hips back to the bed and lifted her feet, letting me choose them completely off her. Nicole spread her peg and for the first fourth dimension I got to see a woman's pussy. Nicole had shaved nigh of it, except for a narrow flight strip just above her labia. Nicole gently pulled my headway to her chthonian 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 stage around my question, almost crushing me, while humping my mouth and moaning. My nerve 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 hip, so I raised them off the bed, and she pulled off my panties.

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

I could finger my pecker, sawing between her thigh, even rubbing across her slit lips as Nicole writhed around on me. Finally, she lifted her articulatio coxae, 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 bass inside her. Once in, she paused a bit, getting us both used to the flavour of me being in her.

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

"I want to continue 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 pecker nearly out of her, then deeply in again. I was in promised land, and wished it could never end, even if I knew she was the right way. I'd spent so practically 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 spell, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it featherbed, right inside me. Fill me up with it."

As I started to cum, I grabbed her ass and held her mingy 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 fellow 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 escape 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 strap. She came back over to the bed and strapped it on herself, so it now appeared that she had a shaft. She had me get on hands and articulatio genus, then got some lubricating substance from a nearby drawer, before lubing up the penis and my ass.

Nicole eased the thing into my ass, until I was well-heeled 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 percentage point, I wasn't going to contend with her. As she began fucking me, I began to get into it. For obvious grounds, she was able-bodied to keep going a lot retentive than lustrelessness even could, and my putz 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 farseeing time before she turned me on my incline 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 daybreak, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me roll in the hay her pussy. We showered together, playing as we washed each other. I went down on her in the cascade and she went down on me after.

"So, did you have any plans for tonight, Lynn ?"

"Nothing particular, 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 precious lilliputian 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 clip with you."

"That's my girl. Now get dressed and scoot."

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

"Hey, baby. Sorry I left you death night, but Toni wanted to get out of there and you seemed all tied up with that brunet you were dancing with."

"That was Nicole. We were enjoying ourselves."

"I figured either she'd give you a lift dwelling house or you'd snatch an Uber or something."

"Actually, she took me back to her topographic point, 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 wager with."

"You're hotter than Toni."

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

"ejaculate on, lady friend. If it weren't for me, you'd have had no sex sprightliness and no chance at that Nicole."

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

"There are affair I can do to you that she can't, unless she's like you."

"She's all fille, but she's got devices. I'm not missing out on anything, and I'm getting matter I could never get with you. I get to trifle with breast, I get to fuck a pussy."

"Are you fucking dumping me, holler ?"

"mat, you've been a unspoilt acquaintance, but I think we both need a change."

"Lynn, how long do you cogitate that kick 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 calendar week at the outside."

"Well then, I'll take that two weeks. In the meanwhile, you have Toni or one of the other many cleaning lady who fall all over themselves to be with you."

"Don't think I'll forget this."

"Just remember, if you out me as a hybridization dresser, you also out yourself as fucking a guy who cross apparel. Your piddling girl might not demand 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 with child evening."

So who was I ? Who did I want to be ? lustrelessness only wanted me as Lynn, and it was starting to face 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 probability to get mine too. Fact is, given a selection, I'd rather be with Nicole or some other cleaning lady than to be with Matt.

I guessed I was bisexual person enough to get off on what I did with Matt, but why give up on adult female if I had any prospect with them ? I was still sitting there in clothes as Lynn, when there was a bash on the threshold. I was puzzled, because I wasn't expecting Nicole, matt, or anyone else for some clock time. I was a short leery of opening the door, when it was unlocked from outside.

I sat there shocked as my baby Karen came in the apartment. She didn't spot me immediately, but turned to close and lock the door. She saw me and her backtalk hung open and she seemed stock-still in plaza until she began moving slowly toward me. Karen got over to me, reached out a hand and touched my face.

"Lenny ? What the nooky ?"

"Karen, I'm not quite trusted how to explicate 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 situation and was going to find fault 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 young woman 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 place. 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 obtain another fair sex, you'll go back to fucking guys ?"

"Karen, please."

"Lenny, it's your life. Fuck who you want. Just don't display up at home or my place dressed like that."

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

"The very squawk is that you look better in those wearing apparel than I did, Lenny."

"I hope you can read and forgive me."

"I forgive you, and I guess I understand that you'll do whatever you have to do in club to get off."

"You were always popular with the guy wire. I could never get any of the girlfriend to give me a s 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 glad 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 make love how long it'll final, 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 lady friend. 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 toilet to fix my makeup and then changed clothes. I'm not sure where the human relationship with Nicole will take me, but I guess fourth dimension will tell .