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

It was a bit inconvenient, since I just had a one chamber home, and not all that big. Being a dainty small brother, I let her induce the bed, while I slept on the couch. She had a ton of clothes and more than filled my closet, leaving little room for my wearing apparel. Beyond that, we had to plowshare one tiny toilet, in shifts, since there was no way we were going to be in there at the same sentence - too small and too weird.

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

Karen left behind all manner of things, skirt, frock, blouses, bras, step-in, skid, physical composition, and all that. After I while I got fascinated with it, which I conjecture was my first mistake. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with womanhood, so even touching the clothes was a turn-on.

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

As prison term went on, I'd lop up completely in Karen's clothes for my self-abuse Roger Huntington Sessions, and even left them on after I'd cum. I began to play with it all a little bit and even began to use some of the makeup she'd left behind. I'd pad her bandeau with air sock or whatever, put on step-in, a skirt, blouse, and shoes, then brush my haircloth in a Sir Thomas More feminine style and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as part of self-abuse. Hell, I needed to get off too, and there were no girls willing to help me. Before long, I'd come home from oeuvre, dress up all girly, and prance around my apartment before getting myself off. I'd even wear one of Karen's old nightgown 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 pop sort, never had any problem getting miss, 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 missy out of it.

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

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

"prick, Matt, I can't get fille to do ordinary diddly-squat with me, much less anything kinky."

"Come on, guy, you must own done something just a little bit out there."

As I said, I'd had too much to tope, and I confessed to dressing up in my sister's clothes to yank off.

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

"Sometimes I'll go full drag, dress, shoes, makeup, and everything."

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

"I don't know, dude. Nobody has ever seen me that way. I'd be freaked out to stimulate someone see me."

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

"Matt, if anyone ever found out, I'd be totally screwed. I'd have to leave town."

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

That was Thursday, and it was already belatedly and I was too drunk and had to work the next day. He asked if I'd garnish up for him the adjacent night. I agreed and told him to come up by after piece of work on Fri, but to give me some metre to get ready.

"Lenny, do you cerebrate you can be ready in an hour ?"

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

…………………………………………………………………………

The adjacent day I really had some sorrow about agreeing to let him see me dressed up. I called him during tiffin and tried to plunk for out, but he said I'd promised and he expected me to keep my promise. I was on boundary all afternoon. I got dwelling house about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented consistency wash, shaved my typeface, wooden leg, 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 sis's clothes. I dried my tomentum and styled it girlish, then put on panties, a bra, a nice bird, and a blouse, then sat down to do composition. By now I had it almost to a skill, putting on cornerstone, then some accents, eyeliner, eye shadow, lipstick, and of course I painted my toenails and fingernails.

I wore some low bounder with open toes, to establish off the toenail polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o'clock. My articulatio genus were wobbly as I walked to the threshold. I looked through the peephole and sure enough it was flatness. I opened the threshold and let him in.

Matt was gaping and staring as he walked in my situation. I closed and locked the door and he turned me around then stepped back to take a just looking 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 queasy. He came back in front of me and grabbed me gently by the shoulders.

"Damn, that is hot, girl."

"I'm not a young lady, 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 interchange back."

"Hold on, Lynn, not so fast. Don't run off on me already. Come sit on the sofa with me."

"I don't think we should do that, Matt. I'm not one of your little girlfriend, I'm Lenny."

"While you're like this, you're Lynn, and I like Lynn. seminal fluid on, please sit on the sofa with me."

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

Matt put and arm around me fast and walked me over to the couch, pulling me down beside him there. He had his arm around my shoulder and seemed to be getting way too a good deal delight out of this.

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

"flatness, this look really weird."

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

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

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

"You've got lots of lady friend - real missy, not fake ones, like me."

"Don't tear yourself down. near of those girls have nothing on you."

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

"Let me contract you out to dinner, Lynn"

"Just let me change into some normal clothes, Matt."

"No, babe, just like this."

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

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

"What if someone sees me - recognizes me ?"

"No one will tell apart you as that nerdy guy."

"Doesn't it bother you to be out in public with a guy in pull ?"

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

"I don't know."

"seminal fluid on, Lynn. A nice dinner, and I'll treat you the way a lady should be treated."

"That makes me feel really weird."

"And maybe a lilliputian turned on ?"

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

"I do, and we should."

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

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

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

"Grab one and your headstone 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 handbag that didn't look too bad with what I was wearing. I took my winder and wallet and dropped them in the purse before turning to Matt.

"I'm really not surely we should be doing this, Matt."

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

Matt actually had money, which is yet another understanding why well-nigh of the girls fell all over each former to get to him. We went downstairs to his trade name new blue BMW Z4 convertible and he opened the threshold 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 prissy restaurant.

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

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

"well, Matt, who is this beautiful ma'am with you tonight ?"

"This is my date, Lynn. Lynn, meet Oliver, he ‘ s another section coach where I work."

"I'm so proud of to foregather you, Oliver."

"And I'm very pleased to run across you, Lynn. lusterlessness is clearly a very golden man. But if you want a change of scenery, give me a call, I'd love to record you a commodity time."

With that, King Oliver handed me a business organization 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."

"wellspring, lustrelessness, if you get tired of Lynn here, feel free to send her my way."

Joseph 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 place would coldcock their date for a chance to take you home."

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

We had a pin-up dinner party and I continued to salute way more than I should have. This whole setting had blown my creative thinker so a great deal I didn't know what else to do. A few other men stopped to speak to us. They invariably seemed to pay unreasonable care to me, when they stopped to lecture to mat. We finished dinner party and I thought Matt would take me back to my place.

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

"Are you sure about that ?"

"You're taking a walk on the wild side, just take a bit longer walk."

matte wouldn't take ‘ no'for an answer and take us to the hottest club in town. This was the variety of place that would never let the like of me inside. They must have had a hundred hoi polloi lined up waiting to get in. lustrelessness was obviously pretty well known, and he walked us up to the nominal head, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a drunkenness and then flatness wanted to dance with me. I felt unknown as shit, but it was a dissipated phone number and I was already half plastered so I went out to dance with him. We danced respective dissolute dances, then a slacken routine came on. I thought we'd go sit down, but instead, Matt pulled me close to him to dance.

He had one manus on my upper back, holding me tight, as his former hired man came down on my ass. He began to caress my ass, which made me wriggle. I could find that matte had a hard-on as he did that. That scared me More than a little, but I wasn't certainly what I could do. I felt helpless as we danced. When the numeral ended, Matt stopped, held me blind drunk, and kissed me.

My knees got so infirm that if he hadn't been holding me miserly, I'd probably have slumped onto the flooring. He gave me a farseeing kiss, and to my surprise, I began to snog him back. I felt conflict - 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 min before he walked me back and we had another drinkable.

I'd been drinking pretty goodness before, but I didn't decelerate down. I was one-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 - mat knew I was a guy dressed like a woman, yet he was acting like I was the very thing.

As I said, I'd been Matt's wingman Sir Thomas More than a few clip, and had seen him this way with women many clock time before. I also knew that in about character he ended up taking those women base and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don't get laid how long we danced and drank, but by the time Matt was cook to leave behind, I was really plastered.

I thought lusterlessness was going to aim me back to my station, but instead he drove me to his apartment. As I said, Matt had money, and he had a very courteous two bedroom apartment - nice article of furniture and all that. Part of me hoped that he was going to let me doss down in the scanty bedroom. Another function of me wanted anything but that.

"lustrelessness, I really need to get menage and change."

"Lynn, honey, there's no rush. Just relax and savor your walk on the wild side."

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

"Matt, we shouldn't be doing this."

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

"I don't know if I'm ready to go any farther."

"Lynn, baby, I've shown you a skilful clock time. I've made you feel ripe. You seem to be getting into this. Can't you serve me feel good too ?"

"What… What did you require me to do ?"

"If zip else, can you at least go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

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

flatness moaned and leaned back, still keeping a hand on my head. I let the headway of his prick slip from between my backtalk, before taking it back and going just a slight farther with it. I bobbed up and down on his prick, gradually taking it mystifying and cryptical into my backtalk. I'd never had a dick in my mouth before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my mouth and lustrelessness seemed to like it. Some precum came from the tip, and it had a salty sense of 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 period of it. By now, flatness was moving his hips, almost fucking my mouth, as he held my pass tight.

flatness moaned loudly and got very fixed as his shaft erupted in my sassing. He held my foreland with both paw as he emptied his formal into my throat. I swallowed his cum and gasped for breath, though it took a duo of swallows to get it all down. It gradually eased and I cleaned his cock off as I pulled my head back from it.

mat pulled me up on him and began to buss me some more. I know he had to taste his own cum in my lip as we kissed, but that didn't seem to get to him. matte continued to snog me and I didn't even realize it as he pulled my doll up over my ass and began to caress my ass through my panty. He even snuck his handwriting into my panty and fondled my bare ass.

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

"Lynn, sister. You are wonderful and beautiful, and I love what we've done, but I need to sleep together you."

"Do it, Matt. Do it."

matt set me down on his bed on my hands and knee joint and pulled down my panties. My shaft, which had been ignored for so long sprang to aid, but matt was occupy in other matter. 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 subway of lube.

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

I felt the head of his hammer at my asshole and tensed for just a second before relaxing. At this distributor 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 flatness took it easily and slacken at foremost, until I really started to get into it.

I soon felt his pelvic arch slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy fuck my ass, I'd have thought you were crazy and told you to leave me the bonk alone. Now flatness was fucking me and I was in promised land. I felt his hammer lantern slide deep in me and fill me up. It turned me on in ways I'd never have expected.

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

lusterlessness collapsed onto me and I collapsed and we rolled onto our English, with his cocksucker still inside me. I was on a intimate highschool and wanted aught more than to preserve feeling his cock in my ass. His pecker was getting flaccid, 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 backrest and side of my neck.

"Lynn, child, you are beautiful, sexy, and wonderful, and I just wish I could stay inside you forever."

"I wish you could stay inside me forever too. I'm yours whenever you want."

"I just might hold you to that, Lynn, baby."

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

……………………………………………………………………………..

I woke the succeeding morning with flatness still spooning me and with his hard pecker pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's surd hawkshaw against my ass, I'd have leapt from bed and buzz off 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 cervix as he eased around so his peter was up against my bunghole. I could feel it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our sides. It was a gentler fucking, instead of the throbbing that we had at the end finally dark, but I still loved it.

My dick got arduous as I felt his weft me up. It was a slow down leisurely screwing, almost loving, and I reached behind me to stroke matt's body as he fucked me. He pressed tight against me as he came deep in my ass. I couldn't believe how much I enjoyed having this guy fuck me, but I knew I wanted it to bear on as long as he wanted me.

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

"I hope we'll have more than just net nighttime and this morning."

"If that's what you want, we don't have to stop with one date."

"I want it. I want your hammer in my ass, in my mouth, wherever you want, and whenever you want."

"I want Lynn. I don't want Lenny."

"I never thought I would, but for you, I'll be Lynn."

"What happens to Lenny ?"

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

By then, Matt's dick had slipped out of my ass and I'd rolled over veneer lustrelessness. I kissed lusterlessness, and he kissed me back and began stroking my soundbox. We spent a farseeing prison term snuggling and touching each other before we got up and went to the shower together. Without my clothes, my bra, my panties, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his cock, I got down on my knees and sucked him off again. With my composition off and hair wet, I didn't smell quite the same, but I dried my pilus, styled it as best I could and got dressed in my wearing apparel from last night. I had a lilliputian war paint in my purse and could do lipstick, eyeliner and a piddling base, to pretend 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 base, and we made a particular date for that eve.

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

Matt took me out again Sabbatum night, and took me back to his shoes. We were not as tired or inebriate and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to sleep, I was starting to sense run afoul. Was this really how I wanted to hold up out my life ? And how long was mat belike to be interested in me ?

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

Occasionally during the week, I would be Lenny and go out as Matt 's wingman. matt always found an attractive char to take dwelling. I was a short overjealous - both of lusterlessness and of the adult female. On rare occasions, I 'd be Lynn during the week, and Matt would come to my place to fuck me. Usually Lynn was a weekend thing, but some weekends, Matt had former plans.

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

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

'' wellspring, honey, your date seems to be ignoring you. ``

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

'' goosey 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 mat and I have kind of an strange human relationship. ``

'' fountainhead, your guy appears to be about fix to ill-treat out with another woman. Would you have any interest in doing the same ? Or are you strictly into hombre ? ``

'' You mean ... you 're interested in women ? ``

'' I like char. I like men. And sometimes I straddle the wrinkle. ``

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

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

'' Well, Lynn, something William Tell me that you straddle the origin. ``

'' And you like that ? ``

'' Let 's dance a bit, beloved. After all, your guy seems to be diverted elsewhere. Unless, of course of action you 're not into cleaning lady. ``

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

Nicole took my deal 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. nether region, as Lenny, I had trouble getting char to even trip the light fantastic toe much with me.

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

At the end of the saltation, Nicole gave me a kiss that almost buckled my knees. I could sense my dick getting harder and barely being restrained by my panty. My judgment was blown. We stood there kissing for I'm not even for sure how long. I'd never had a woman snog me like that before, and I was in no hurriedness for it to end.

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

"well, Lynn honey, it looks like you lost your guy."

"Well, I guess I don't mind, at least as long as I have you for company."

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

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

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

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

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

"So maybe you never met the right lady friend before. As long as you're open minded and elastic, I think we can have mint of fun."

I felt a minuscule uncertain. Nicole was pretty and she seemed uncoerced. I just didn't understand why she'd have any interest in me - not after knowing that I was a guy dressed as a girl who'd been out with a guy. Look, I'd never had any woman willing to give me the time of day, much lupus erythematosus get confidant with me. Nicole figured out what I really was and still seemed concerned. Now that was kinky.

lustrelessness had left me and gone off. I could either call an Uber or observe out what Nicole had in idea. Honestly it was probably better than what Matt had done, even though I seemed to revel fucking Matt. I sat for respective seconds, just pondering the hypothesis. I looked at Nicole who sat there with a little puzzling grinning on her nerve, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walking on the raving mad side of meat anyhow, why not walk a niggling farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the cabaret. She had a car nearby, nothing as expensive or flashy as Matt's BMW, but a Nissan 370Z a couple of years old. It was certainly nicer than my eight yr 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 charwoman and knew what I was down below.

I stood slightly puzzled for a second gear 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 ass and started the car. Before she put it in gear, she smiled at me again and gave me a quick kiss.

"We'll go to my property, Lynn, unless you have an objection."

"Best offer I've had in a hanker time."

"Better than your minuscule boyfriend ?"

"No question."

We were stopped, getting set up to decease the parking lot. I leaned over and gave Nicole a osculation. She smiled and stroked my principal, before taking us out on the road. She drove us a few knot to her apartment. It was on the irregular story and we had to take the air a flight of stairs, but we had our arms around each former, giggling and petting each early as we went.

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

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

"I really just started dressing up in my sister's clothes as a turn-on. I told Matt one fourth dimension when I was drunk and he wanted me to dress up for him."

"Obviously, you did."

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

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

"Oh my God, no. Even now, the sole fourth dimension I go out this way is with him."

"But you were into guys ?"

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

"have you been with any other guy wire than him ?"

"Never. Most 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 care Lenny. How do you feel about that ?"

"I'd honey 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 lilliputian beau flatness ?"

"I think he's getting a piffling 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 posterior tonight or tomorrow morning."

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

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

I was more than happy to do so, though my hired hand were shaking as I began to undo the push button. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her chick, and she asked me to pull it sluttish and take aim it off her. She sat there with only her bra on the amphetamine half of her body. I hardly even noticed as she took my blouse off me.

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

My bra, of form, was filled with padding, not sin, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the cushioning, it still sent a shiver of pleasure through my body. She had both bridge player on what would have been my booby, if I had any, so I placed my early script on her other breast.

I was a little concerned about pushing it too far, but Nicole seemed to get even more release on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the one I wore for some prison term, 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 autumn forward. She had her arms around me, as I had mine around her, so the bra didn't fall off. She reached behind me and unhooked my bra. We continued to kiss for a while before she leaned back to allow our bandeau to fall off each of us.

My bra and padding fell to the floor, leaving my bare chest out there. I got my first look at Nicole's chest - actually the first chest I'd ever seen live and in person. I wanted to extend to them but I was hesitant. I didn't want to motivate too fast and spoil affair. Again Nicole put my deal on one of her booby, then began to stroke my apartment, boobless, chest.

Her boobs felt flummox, warm, balmy, and just so wonderful. I began to fondle her boob and nipple as Nicole played with my bureau. After a fiddling patch, she stopped kissing me and guided my mouth down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the bosom right wing on her nipple.

Nicole leaned back, pulling me with her as I began to kiss and thrash her chest 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 bosom seemed to revel in my attention. After a bit, she shifted my head over to the other boob, and I began to fall in it the same tending that I'd been giving its partner.

I spent a retentive time kissing and pleasing her breasts, before Nicole clutched my head tightly to her as she moaned and writhed on the couch. 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 air me on my way. Instead Nicole stood and pulled me to my animal foot and led me by the script into her sleeping accommodation. 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 chick slide down her body onto the floor. She stepped out of the chick, then kicked off her place. She now wore only panties, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my wench. My scanty were having trouble restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

"Lynn, I'll please you, but I want you to please me first. okey ?"

"Anything you want, Nicole."

"low, choose off my panties."

I moved down her trunk and Nicole lifted her hips off the bed. I slid her panties down and once they were clear of her ass, she dropped her hips back to the bed and lifted her foot, letting me use up them completely off her. Nicole spread her legs and for the commencement fourth dimension I got to see a woman's kitty. Nicole had shaved near of it, except for a narrow down strip just above her labia. Nicole gently pulled my capitulum to her nether realm, though I had no estimate what I was supposed to do.

"okay, baby. snog it, lick it, stick that tongue in me."

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

I was still in full makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my step-in off, she kissed the brain of my cocksucker, which was as gruelling as I've ever seen it. looking at, I'm no great shakes in that section, but I've got about six column inch, and it was in its full glory as Nicole slid back up my body.

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

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

"I want to remain 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 hip joint taking my dick nearly out of her, then deeply in again. I was in heaven, and wished it could never end, even if I knew she was right. I'd spent so 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 patch, I realized I was getting close.

"I'm going to cum, Nicole."

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

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

"I know that isn't quite what your young man would do to you, but I hope you enjoyed it anyhow, Lynn."

"That was wonderful. well 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 strap. 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 script and knees, then got some lube from a nearby drawer, before lubing up the phallus and my ass.

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

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

………………………………………………………………………………..

We woke up in the morning, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me fuck her kitty-cat. 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 program for tonight, Lynn ?"

"Nothing specific, but I'd beloved to spend 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 menage, 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 clock time with you."

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

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

"Hey, babe. Sorry I left you survive Nox, 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 render you a lift home or you'd haul an Uber or something."

"Actually, she took me back to her piazza, and I spent the dark there."

"So she was nerveless with Lynn and what Lynn was ?"

"Yeah, she was."

"So, Lynn, I was thinking that tonight…"

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

"You're hotter than Toni."

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

"come on, missy. If it weren't for me, you'd have had no sex liveliness and no chance at that Nicole."

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

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

"She's all miss, 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 fiddle with boobs, I get to have sex a pussy."

"Are you fucking dumping me, bitch ?"

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

"Lynn, how long do you conceive that cunt will go before she dumps you ?"

"Don't know, but I'm going to run with this for as hanker as I can."

"I give it two workweek at the outside."

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

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

"Just recall, if you out me as a hybridization dresser, you also out yourself as fucking a guy who cross attire. Your little girlfriend might not take that very well."

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

"And you've gotten defrayal for that. And if or when Nicole ditch me, if you aren't too big a kick, you might even get more. In the interim, I hope you have a groovy evening."

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

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

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

"Lenny ? What the fuck ?"

"Karen, I'm not quite sure enough how to excuse this."

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

"You're obviously in my clothes."

"Yes. It's sort of a long story."

"Are you wearing my panty and bras too ?"

"I am."

"I got a fully grown blank space and was going to cull 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 lady friend I spent the nighttime with happy."

"A fille ? A tangible little girl ? Not some in between or fake matter ?"

"Nicole is a real womanhood. For some ground she gets off on being with me like this."

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

I looked at my shoes. I couldn't aspect Karen in the expression. 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 happen another cleaning woman, you'll go back to fucking guy rope ?"

"Karen, please."

"Lenny, it's your living. roll in the hay who you want. Just don't show up at home or my place dressed like that."

I was crying by this time. Karen made me ashamed of what I'd done and what I'd become. At the Saami time, I needed have it away too, and if being Lynn was what kept Nicole then I was going to carry on to be Lynn. I wept on Karen's shoulder, and she took some pathos on me and stroked my head and tried to soothe me. It took a spell before I regained my composure.

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

"I hope you can infer and forgive me."

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

"You were always popular with the guys. I could never get any of the girl to move over me a second look."

"So you dressed this way to get cat ?"

"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 comfy, it was better than being alone."

"And this lady friend you're with now ?"

"Saw me, liked me, and figured out what I was. She liked cleaning woman and men and seemed happy with me dressed like this."

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

"I don't bed 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 girl. And I'm not going to wear upon any of the apparel I left here, so they're all yours."

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