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

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

Karen stayed with me for about six months before getting her own place and moving out. Her place was small-scale than mine, so while she took near of her poppycock, 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 seat until she could afford a bigger lieu. Again, being a squeamish brother, I let her do it.

Karen left behind all way of things, skirts, apparel, blouses, bras, panties, brake shoe, makeup, and all that. After I while I got fascinated with it, which I guess was my initiative misunderstanding. I started by just touching some of the clothes. I was a fairly nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.

I started by just touching her dress while touching myself, then jerking off until I came. I progressed to smelling the apparel and draping some of them over my mind 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 dress. That seemed to be a bigger turn-on and her clothes seemed to fit, since we were almost the Sami size.

As fourth dimension went on, I'd coiffure up completely in Karen's clothes for my self-abuse session, 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 war paint she'd left behind. I'd pad her brassiere with wind cone or whatever, put on step-in, a skirt, blouse, and shoes, then brush my hair in a more feminine manner and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. hellhole, I needed to get off too, and there were no young lady will to help me. Before retentive, I'd come dwelling from work, coiffe up all girly, and strut around my apartment before getting myself off. I'd even wear one of Karenic's old nighties to bed afterward.

I had a few booster who I'd hang out with occasionally. One of them, who I'd known since high school was Matt. He was always the democratic sort, never had any problem getting girls, and often seemed to possess one or more than hanging off him. He'd occupy me along as a wingman sometimes, though I never managed to get any lady friend out of it.

One nighttime he and I were drinking, and I'd had more than I should have, and we began talking. He started telling me about how he got some dame to let him finger her in public in a eating place. He said they'd also gone to a motion picture theater, 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 nappy affair you've even done ?"

"Shit, Matt, I can't get fille to do ordinary shit with me, much less anything kinky."

"seminal fluid on, guy, you must have done something just a little bit out there."

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

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

"Sometimes I'll go full-of-the-moon retarding force, clothes, shoes, makeup, and everything."

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

"I don't know, dude. cypher has ever seen me that way. I'd be freaked out to have someone see me."

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

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

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

That was Thursday, and it was already tardy and I was too pledge and had to do work the adjacent day. He asked if I'd enclothe up for him the adjacent night. I agreed and told him to come by after work on Friday, but to commit me some time to get ready.

"Lenny, do you think you can be ready in an time of day ?"

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

…………………………………………………………………………

The adjacent day I really had some declination about agreeing to let him see me dressed up. I called him during lunch and tried to back out, but he said I'd promised and he expected me to go along my promise. I was on boundary all afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented soundbox wash, shaved my face, leg, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the sentiment of having this guy see me in my baby's clothes. I dried my haircloth and styled it girlish, then put on panties, a bra, a nice skirt, and a blouse, then sat down to do composition. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye phantasma, lip rouge, and of row I painted my toenails and fingernails.

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

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

"shucks, 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 piece of work. How about I call you Lynn ?"

"OK, Matt, you got to see me, now let me change back."

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

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

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

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

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

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

"Matt, this feels really weird."

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

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

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

"You've got peck of girls - real girls, not fake unity, like me."

"Don't shoot down yourself down. virtually of those lady friend have nothing on you."

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

"Let me subscribe to 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, coddle. You look absolutely stunning."

"What if someone sees me - recognizes me ?"

"No one will recognize you as that nerdy guy."

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

"No one but you and I will screw, and besides I like a little 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 little turned on ?"

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

"I do, and we should."

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

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

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

"catch one and your keys and let's go."

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

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

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

mat actually had money, which is yet another reason why to the highest degree of the girls fell all over each former to get to him. We went downstairs to his make new bluing BMW Z4 convertible and he opened the threshold of the car for me. I managed to sit down in a somewhat ladylike fashion - I don't think I showed too much. He got in and tug us to a very nice restaurant.

He used valet parking and walked me in, holding the door for me. I still felt Wyrd as shit, but just tried to ignore how I looked and revel myself. matt ordered a dainty bottle of vino for us, and I really needed something to drink. I downed my first of all crank before he'd taken more than than a pair sips of his wine. mat poured me another methamphetamine hydrochloride, but I took it a picayune 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 wiggle in my seat. One guy who works with mat stopped at the table to babble out with us. I'd met him respective times before, but he clearly didn't tell apart me.

"well, matt, who is this beautiful lady with you tonight ?"

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

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

"And I'm very proud of to see you, Lynn. matt is clearly a very lucky man. But if you want a variety of scenery, give me a call, I'd love to show you a good time."

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

"Thanks, Oliver, but I'm not really looking for anyone else at the present."

"well, Matt, if you get tired of Lynn here, palpate free to send her my way."

Oliver bent down and kissed my cheek before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot bird. Half the men in this shoes would ditch their date for a probability to study 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 drink way more than I should have got. This completely fit had blown my thinker 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 care to me, when they stopped to talk to mat. We finished dinner and I thought matt would charter 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 baseless face, just take a bit longer walk."

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

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

He had one hand on my upper back, holding me tight, as his early manus came down on my ass. He began to fondle my ass, which made me wriggle. I could feel that Matt had a hard-on as he did that. That scared me to a greater extent than a piddling, but I wasn't certainly what I could do. I felt helpless as we danced. When the number ended, lusterlessness stopped, held me tight, and kissed me.

My knee got so weak that if he hadn't been holding me smashed, I'd probably have slumped onto the flooring. He gave me a foresighted kiss, and to my surprisal, I began to buss 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 second before he walked me back and we had another drink.

I'd been drinking pretty good before, but I didn't slow down. I was half afraid of what was going to happen, and felt like I needed to be very drunk. We drank more and danced more, and the more we drank and danced, the more Matt kept feeling me up and kissing me. My mind was blown - 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 Matt's wingman to a greater extent than a few times, and had seen him this way with women many times before. I also knew that in most cases he ended up taking those char household and fucking them. That scared me, but also seemed to twist me on, and it scared me that I was turned on by it. I don't know how hanker we danced and drank, but by the metre Matt was ready to depart, I was really plastered.

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

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

"Lynn, love, there's no hurry. Just relax and enjoy your base on balls on the wild side."

Matt got us each a swallow, like I needed any more alcohol, and sat me down on the sofa, sitting right alongside me. Matt put his arm around me and pulled me tight, then began to kiss me. He started just with the lips, then added in some tongue, while feeling up my ass and my fake dope. 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 care it, and I told you I occasionally like kinky shit."

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

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

"What… What did you want me to do ?"

"If zilch 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 drawers with his other deal. He pulled out his cock, which was already hard and standing straight up. He kissed me again, then gently pushed my head down toward his dick. I got close and looked at it. It was long and hard and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the heading of his gumshoe between my lips.

matte moaned and leaned back, still keeping a bridge player on my brain. I let the head of his cock slip from between my mouth, before taking it back and going just a slight farther with it. I bobbed up and down on his peter, gradually taking it deeper and cryptic into my mouth. I'd never had a dick in my lip before and it felt unknown, but in another way, it felt very natural.

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

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

Matt pulled me up on him and began to kiss me some more. I know he had to smack his own cum in my sass as we kissed, but that didn't seem to vex him. lusterlessness continued to kiss me and I didn't even actualize it as he pulled my skirt up over my ass and began to caress my ass through my panty. He even snuck his hand into my scanty and fondled my bare ass.

I don't know why I didn't observation, I don't know why I didn't stop him. Maybe I was enjoying it all too much, and maybe I was just too tope. Before I even realized it, matte had removed my chick and blouse and was carrying me into his sleeping room. I was so far gone at this spot I didn't know or wish, or maybe it was what I really wanted.

"Lynn, baby. You are howling and beautiful, and I love what we've done, but I need to fuck you."

"Do it, Matt. Do it."

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

flatness 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 moment finger in and began to finger fuck my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the binding of my neck opening as he pulled his fingers out of my ass.

I felt the headway of his pecker at my son of a bitch and tensed for just a arcsecond before relaxing. At this period, I think I wanted him as much as he wanted me. I felt the head get just inside me and I sighed and moved my ass back, getting more of him in me. It hurt a bit, but lustrelessness took it easy and slow at outset, 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 screw my ass, I'd have thought you were crazy and told you to leave alone me the be intimate alone. Now Matt was fucking me and I was in heaven. I felt his shaft slide oceanic abyss in me and satiate me up. It turned me on in ways I'd never have expected.

matt slid his shaft in me so far, I could almost experience him jab my belly. I'd almost swear I saw my tummy bulge as he got all the way in. In spite of whatever arriere pensee I'd had, I was loving every second base of this, every stroke of his cock. I wanted his dick in my ass, and when he came with a gush in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our sides, with his dent still inside me. I was on a sexual high and wanted nada more than to maintain feeling his cock in my ass. His dick was getting softer, but I wanted to keep him in me as long as I could. As we came off our mellow, lusterlessness began to stroke my shoulders and kiss the backrest and side of my neck.

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

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

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

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

……………………………………………………………………………..

I woke the next morning with matt still spooning me and with his hard cock pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's backbreaking peter against my ass, I'd have leapt from bed and set about out of the way as fast as I could. Instead, I moaned and moved my ass around against his prick.

Matt woke up and began stroking me and kissing the back of my neck as he eased around so his prick was up against my asshole. 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 nookie, instead of the pound that we had at the end in conclusion Night, but I still loved it.

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

"Lynn, baby, thank you for last dark, and for this first light too."

"I hope we'll have more than just finale night and this morning."

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

"I want it. I want your prick in my ass, in my oral cavity, 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, flatness's dick had slipped out of my ass and I'd rolled over cladding Matt. I kissed Matt, and he kissed me back and began stroking my dead body. We spent a long time kissing and touching each other before we got up and went to the shower together. Without my clothes, my bra, my scanty, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his prick, I got down on my knees and sucked him off again. With my makeup off and haircloth wet, I didn't spirit quite the Lapp, but I dried my hair, styled it as topper I could and got dressed in my clothes from last dark. I had a niggling war paint in my purse and could do lipstick, eyeliner and a little al-Qa'ida, to make me more like Lynn.

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

When I got home, I looked at myself in the mirror, then just slumped onto the frame and rock my school principal. 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 figure out it out along the way. For now, at least, I guess I was Lynn, until Matt got tired of me or I got tired of it all. I guess Karen's extra clothes were now Lynn's wearing apparel till encourage notice.

Matt took me out again Saturday night, and took me back to his space. We were not as tired or drunkard and after I went down on him, he fucked me three prison term. I enjoyed it but as I drifted off to sleep, I was starting to experience conflicted. Was this really how I wanted to endure out my biography ? And how long was mat likely to be matter to in me ?

We fucked a couple more times the next morning and I went abode. I decided that Lynn would only be on Fri and Saturday nighttime. I was going to hold up and play as Lenny, the rest of the prison term. It was hard. We all want to be appreciated. We all want someone to conceive we are special. Lenny is n't special to anyone, though Lynn is.

Occasionally during the hebdomad, I would be Lenny and go out as Matt 's wingman. mat always found an attractive charwoman to take base. I was a little jealous - both of Matt and of the cleaning woman. On rare occasions, I 'd be Lynn during the calendar week, and Matt would do to my place to sleep with me. Usually Lynn was a weekend matter, but some weekends, flatness had early plans.

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

One Friday night, Matt and I were at a golf-club and I was being Lynn, though Matt seemed to be giving most of his tending 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 human body, b-cup boobs, and a pretty face.

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

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

'' gooselike 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 Matt and I have kind of an strange kinship. ``

'' Well, your guy appears to be about ready to abuse out with another adult female. Would you have any interest in doing the same ? Or are you strictly into guy rope ? ``

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

'' I like fair sex. I like men. And sometimes I straddle the line. ``

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

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

'' well, Lynn, something William Tell me that you straddle the tune. ``

'' And you like that ? ``

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

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

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

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

At the end of the dance, Nicole gave me a osculation that almost buckled my knees. I could finger my dick getting harder and barely being restrained by my step-in. My head was blown. We stood there kissing for I'm not even sure how long. I'd never had a cleaning lady kiss me like that before, and I was in no hurry for it to end.

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

"wellspring, Lynn dearest, it looks like you lost your guy."

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

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

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

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

"I know your coming into court belies what you have down below, but I'm practiced with that. As long as you like lady friend, I think we can experience some fun."

"I like girls, I just never had very much hazard before."

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

I felt a little changeable. 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 miss who'd been out with a guy. Look, I'd never had any cleaning lady leave to give me the time of day, much LE get intimate with me. Nicole figured out what I really was and still seemed concerned. Now that was kinky.

Matt had left me and gone off. I could either call an Uber or happen out what Nicole had in thinker. Honestly it was probably better than what flatness had done, even though I seemed to enjoy fucking lusterlessness. I sat for various seconds, just pondering the possibilities. I looked at Nicole who sat there with a picayune enigmatic smiling on her fount, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walking on the wild side anyhow, why not walk a little farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the club. She had a car nearby, zilch as expensive or flashy as Matt'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 Saame, but Nicole was a cleaning lady and knew what I was down below.

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

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

"Best offering I've had in a foresighted time."

"punter than your little boyfriend ?"

"No question."

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

Nicole had a nice short one sleeping accommodation place, clearly feminine, with a muffle floral sofa and chairs, along with some art mark on the bulwark. The print were largely of cleaning woman and men, along with a few where it wasn't quite clear if it was male person or female. She walked me over and we sat on the sofa, and she put her arm around me.

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

"I really just started dressing up in my Sister's clothes as a turn-on. I told Matt one clock time when I was drunk and he wanted me to garment 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 lonesome clock time I go out this way is with him."

"But you were into guy rope ?"

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

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

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

"wellspring, I like Lynn, and I might even care 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 clip ?"

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

"What about your little boyfriend lusterlessness ?"

"I think he's getting a little shopworn of me."

"What if he isn't ?"

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

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

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

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

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

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

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

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

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

My bra and padding fell to the floor, leaving my bare dresser out there. I got my first-class honours degree expression at Nicole's boob - actually the low white meat I'd ever seen live and in soul. I wanted to bear on them but I was hesitating. I didn't want to move too fast and featherbed thing. Again Nicole put my hired man on one of her pinhead, then began to stroke my level, boobless, chest.

Her boobs felt pose, ardent, soft, and just so terrific. I began to caress her titty and tit as Nicole played with my dresser. After a little while, she stopped kissing me and guided my mouth down to one of her delectable boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the tit right wing on her nipple.

Nicole leaned back, pulling me with her as I began to kiss and lick her breast all over. Her mammilla got very hard and stood out farther than I realized they even could. Not only was I reveling in this, her breast seemed to whoop it up in my tending. After a bit, she shifted my psyche over to the other boob, and I began to have it the Sami attention that I'd been giving its partner.

I spent a farseeing 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 send me on my way. Instead Nicole stood and pulled me to my human foot and led me by the hand into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, baby, unzip my skirt."

I unzipped her and she let the skirt slide down her body onto the floor. She stepped out of the doll, then kicked off her place. She now wore only panties, and I could see a decidedly wet topographic point in the front of them, as Nicole unzipped my dame. 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."

"First, read off my panties."

I moved down her organic structure and Nicole lifted her pelvic girdle off the bed. I slid her panties down and once they were authorise of her ass, she dropped her hips back to the bed and lifted her fundament, letting me demand them completely off her. Nicole spread her peg and for the first sentence I got to see a woman's pussy. Nicole had shaved near of it, except for a minute funnies just above her labia. Nicole gently pulled my head to her nether region, though I had no idea what I was supposed to do.

"O.K., sister. Kiss it, lick it, stick that tongue in me."

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

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

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

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

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

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

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

"I'm going to cum, Nicole."

"Do it baby, right inside me. make full 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 beau would do to you, but I hope you enjoyed it anyhow, Lynn."

"That was marvelous. Better than anything I've ever done with Matt."

"We don't want you to omit out on anything though."

"What do you mean."

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

Nicole eased the matter into my ass, until I was well-heeled with it, then began to slowly jazz my ass with this strap-on. I wasn't sure I wanted her to do that, but at this detail, I wasn't going to debate with her. As she began fucking me, I began to get into it. For obvious cause, she was able-bodied to save 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 twist on her even through that. We kissed for a yearn time before she turned me on my position and spooned me, with her strap-on pressing up against my ass. We fell asleep that way and I had the most contented nap that I've had in ages.

………………………………………………………………………………..

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

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

"cypher particular, but I'd honey to drop it with you, if you're available."

"That sounds great. I've got some errands and affair to do this afternoon, so you need to get your cunning little ass household, and I'll see Lynn back here at seven."

"You'd rather be with me as Lynn than Lenny ?"

"For now. Do you have a problem with that ?"

"Not as long as I can spend my time with you."

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

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

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

"That was Nicole. We were enjoying ourselves."

"I figured either she'd give you a lift domicile or you'd gimmick an Uber or something."

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

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

"Yeah, she was."

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

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

"You're hotter than Toni."

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

"Come on, young woman. If it weren't for me, you'd have had no sex life sentence and no probability at that Nicole."

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

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

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

"Are you fucking dumping me, bitch ?"

"Matt, you've been a good friend, but I think we both need a change."

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

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

"I give it two weeks at the outside."

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

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

"Just remember, if you out me as a interbreeding dresser, you also out yourself as fucking a guy who cross wearing apparel. Your piddling girlfriends might not take that very well."

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

"And you've gotten defrayment for that. And if or when Nicole dumps me, if you aren't too big a beef, you might even get Sir Thomas More. In the meantime, I hope you have a nifty evening."

So who was I ? Who did I want to be ? Matt only wanted me as Lynn, and it was starting to depend 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 former woman than to be with Matt.

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

I sat there shocked as my sister Karenic came in the apartment. She didn't dapple me immediately, but turned to shut and lock the doorway. She saw me and her mouth hung open and she seemed wintry 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 screw ?"

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

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

"You're obviously in my clothes."

"Yes. It's kind of a foresightful story."

"Are you wearing my panties and bras too ?"

"I am."

"I got a bigger place and was going to pick up the eternal 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 to a greater extent stuff."

"So is dressing like this what makes you happy ?"

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

"A girl ? A real girl ? Not some in between or manipulate affair ?"

"Nicole is a real woman. For some grounds 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 facial expression Karenic in the face. She understood immediately.

"ass. You mean you did that too ?"

"As long as I have Nicole, I don't want or need any guys."

"But if she dumps you and you can't find another woman, you'll go back to fucking guy wire ?"

"Karenic, please."

"Lenny, it's your biography. Fuck who you want. Just don't show up at menage or my billet dressed like that."

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

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

"I hope you can realise and forgive me."

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

"You were always popular with the hombre. I could never get any of the girls to give me a minute 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 well-situated, 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 be intimate how long it'll live on, but I'll do what I have to do to keep it going."

"Should I still call up 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 lav to fix my makeup and then changed clothes. I'm not sure where the human relationship with Nicole will take away me, but I guess time will tell .