It started kind of strange. I am or at least was Len or Lenny - Elmore Leonard to my mother - a guy in my early 20s, kind of shortsighted and slender. I had a baby, Karen who was a few long time 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-time back together.

It was a bit inconvenient, since I just had a one bedroom home, and not all that big. Being a prissy fiddling brother, I let her throw the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving piddling room for my clothes. Beyond that, we had to share one tiny bathroom, in shifts, since there was no way we were going to be in there at the same time - too minor and too weird.

Karen stayed with me for about six months before getting her own property and moving out. Her piazza was little than mine, so while she took most of her stuff, 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 bequeath them at my place until she could afford a braggy place. Again, being a skillful crony, I let her do it.

Karen left behind all mode of things, skirts, dresses, blouses, bras, panty, place, makeup, and all that. After I while I got fascinated with it, which I guess was my first mistake. I started by just touching some of the apparel. I was a middling nerdy guy who could never get anywhere with women, 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 heading 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 apparel. That seemed to be a bigger turn-on and her wearing apparel seemed to fit, since we were almost the same size.

As time went on, I'd groom up completely in Karen's clothes for my self-abuse Sessions, and even left them on after I'd cum. I began to play with it all a footling bit and even began to use some of the composition she'd left behind. I'd pad her bras with air-sleeve or whatever, put on panties, a skirt, blouse, and shoe, then brush my hairsbreadth in a more feminine elan and learned how to do my makeup.

It all seemed guiltless. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no girls willing to avail me. Before foresightful, I'd come place from work, habilitate up all girly, and prance around my flat before getting myself off. I'd even wear one of Karen's old nightdress to bed afterward.

I had a few friends who I'd hang out with occasionally. One of them, who I'd known since high school was Matt. He was always the pop sort, never had any trouble getting girls, and often seemed to have one or more hanging off him. He'd take me along as a wingman sometimes, though I never managed to get any girls out of it.

One night he and I were drinking, and I'd had Sir Thomas 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 movie theatre, sat way in spinal column, and she hiked up her annulus, sat on his lap, and fucked him in the theatre during the movie.

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

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

"ejaculate on, guy, you must have done something just a piffling bit out there."

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

"Seriously, Len. Do you just slide on her step-in to get turned on or do something more ?"

"Sometimes I'll go broad drag, clothes, horseshoe, composition, 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 have someone see me."

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

"mat, 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 Th, and it was already late and I was too sot and had to exercise the future day. He asked if I'd dress up for him the next night. I agreed and told him to issue forth by after piece of work on Friday, but to give me some time to get ready.

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

"I think so. I get dwelling about six, so come by my billet around seven."

…………………………………………………………………………

The side by side day I really had some regrets about agreeing to let him see me dressed up. I called him during lunch and tried to back out, but he said I'd promised and he expected me to observe my promise. I was on edge all afternoon. I got nursing home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented body wash, shaved my face, legs, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the intellection of having this guy see me in my sister's clothes. I dried my hair and styled it girlish, then put on scanty, a bra, a nice skirt, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on base, then some idiom, eyeliner, eye phantom, lipstick, and of course I painted my toenails and fingernails.

I wore some low heels with undefendable toes, to prove off the toenail finish 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 unquiet when the doorbell rang at seven o'clock. My knees were wobbly as I walked to the door. I looked through the peephole and certainly sufficiency it was Matt. I opened the door and let him in.

lusterlessness was gaping and staring as he walked in my property. I closed and locked the door and he turned me around then stepped back to contain a unspoiled look at me. After looking at me a bit, he walked around behind me. He stroked my hair's-breadth as he walked behind me, which made me nervous. He came back in front of me and grabbed me gently by the shoulders.

"tinker's dam, that is hot, girl."

"I'm not a girl, I'm just dressed like one. I'm Lenny, you know that."

"The way you look, Lenny doesn't work. How about I call you Lynn ?"

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

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

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

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

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

Matt put and arm around me 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 pleasure out of this.

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

"Matt, this feels really weird."

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

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

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

"You've got wad of girls - real daughter, not fake ones, like me."

"Don't pull yourself down. most of those girls have nothing on you."

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

"Let me take you out to dinner, Lynn"

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

"No, babe, just like this."

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

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

"What if individual 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 drag ?"

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

"I don't know."

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

"That makes me finger 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 drew me to my ft. He wrapped his munition around me and pulled me conclude. I think my centre were the size of saucers and my articulatio genus were getting washy as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the room access. When we got there, he stopped and turned.

"Do you need a bag, key fruit, and such ?"

"I think Karenic left a couplet of purse here too."

"snap 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. matt went with me in the bedroom, and I went in the W.C. and found a handbag that didn't look too bad with what I was wearing. I took my keystone 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 fine, Lynn."

Matt actually had money, which is yet another reason why most of the girls fell all over each other to get to him. We went downstairs to his brand new dingy BMW Z4 exchangeable and he opened the door 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 beat back us to a very nice restaurant.

He used gentleman's gentleman parking and walked me in, holding the door for me. I still felt Wyrd as son of a bitch, but just tried to discount how I looked and savor myself. Matt ordered a nice bottle of wine for us, and I really needed something to salute. I downed my number 1 ice before he'd taken to a greater extent than a yoke sips of his wine. Matt poured me another glass, but I took it a lilliputian slower.

The waiter seemed very taken with me, and when he thought I didn't notice, tried looking down my blouse. various other men seemed to detect me, which made me squirm in my seat. One guy who works with matt stopped at the table to mouth with us. I'd met him respective times before, but he clearly didn't discern me.

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

"This is my date, Lynn. Lynn, sports meeting Oliver, he ‘ s another department manager where I work."

"I'm so pleased to cope with you, Oliver."

"And I'm very pleased to run across you, Lynn. Matt is clearly a very lucky man. But if you want a change of scenery, give me a Call, I'd love to express you a skillful time."

With that, Oliver handed me a occupation menu. I think I turned red, but slipped it in my purse.

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

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

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

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot chick. Half the men in this billet would floor their particular date for a hazard to take you home."

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

We had a lovely dinner party and I continued to drink way more than I should have. This hale tantrum had blown my brain so practically I didn't know what else to do. A few other men stopped to talk to us. They invariably seemed to pay unreasonable care to me, when they stopped to spill the beans to Matt. We finished dinner and I thought Matt would take me back to my place.

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

"Are you sure about that ?"

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

Matt wouldn't take ‘ no'for an resolution and get us to the hottest club in town. This was the sort of place that would never let the the like of me inside. They must have had a c 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 shit, but it was a fast number and I was already half plastered so I went out to trip the light fantastic with him. We danced various firm terpsichore, then a slow 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 pixilated, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could palpate that Matt had a erection as he did that. That scared me Thomas More than a picayune, but I wasn't sure what I could do. I felt lost as we danced. When the telephone number ended, lusterlessness stopped, held me smashed, and kissed me.

My knees got so decrepit that if he hadn't been holding me tight, I'd probably have slumped onto the flooring. He gave me a retentive kiss, and to my surprise, I began to kiss him back. I felt conflicted - I didn't feel like I should be doing this, not with a guy, but I seemed to be enjoying it. We kissed for a minute before he walked me back and we had another potable.

I'd been drinking pretty good before, but I didn't slow down. I was half afraid of what was going to go on, 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 brain was blown - mat knew I was a guy dressed like a fair sex, yet he was acting like I was the real thing.

As I said, I'd been Matt's wingman more than a few times, and had seen him this way with cleaning woman many times before. I also knew that in almost causa he ended up taking those cleaning woman home and fucking them. That scared me, but also seemed to plow me on, and it scared me that I was turned on by it. I don't acknowledge how long we danced and drank, but by the prison term Matt was prepare to go away, I was really plastered.

I thought Matt was going to drive me back to my place, but instead he drove me to his apartment. As I said, Matt had money, and he had a very skillful two bedroom apartment - nice article of furniture and all that. Part of me hoped that he was going to let me crash in the supererogatory sleeping accommodation. Another percentage of me wanted anything but that.

"Matt, I really ask to get menage and change."

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

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

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

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

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

"Lynn, infant, I've shown you a good sentence. I've made you finger commodity. You seem to be getting into this. Can't you facilitate me feel safe too ?"

"What… What did you want me to do ?"

"If nothing else, can you at least go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

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

Matt moaned and leaned back, still keeping a manus on my head. I let the head of his cock slip from between my sassing, before taking it back and going just a little farther with it. I bobbed up and down on his cock, gradually taking it deep and cryptic into my mouth. I'd never had a dick in my oral fissure before and it felt unknown, but in another way, it felt very natural.

I slowly but steadily fucked his peter with my mouth and Matt seemed to like it. Some precum came from the tip, and it had a salty preference, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the al-Qaida of his tool as I sucked the ease of it. By now, Matt was moving his hips, almost fucking my sassing, as he held my head tight.

lustrelessness moaned loudly and got very rigid as his cock erupted in my mouth. He held my drumhead with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for breathing time, though it took a couple of sup to get it all down. It gradually eased and I cleaned his peter off as I pulled my head back from it.

lustrelessness pulled me up on him and began to snog me some more. I know he had to taste his own cum in my mouth as we kissed, but that didn't seem to chafe him. matt continued to kiss me and I didn't even recognize it as he pulled my skirt up over my ass and began to caress my ass through my panties. He even snuck his manus into my panties and fondled my bare ass.

I don't know why I didn't notice, I don't know why I didn't stop him. Maybe I was enjoying it all too much, and maybe I was just too inebriate. Before I even realized it, Matt had removed my chick and blouse and was carrying me into his sleeping accommodation. I was so far gone at this point I didn't know or handle, or maybe it was what I really wanted.

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

"Do it, flatness. Do it."

mat set me down on his bed on my workforce and knees and pulled down my step-in. My cock, which had been ignored for so foresighted sprang to attention, but lustrelessness was worry in other things. He took off his trouser and shirt and got in bed behind me. He reached into a drawer in the table beside the bed and got a thermionic tube of lube.

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

I felt the head of his putz at my asshole and tensed for just a second before relaxing. At this point, I think I wanted him as much as he wanted me. I felt the head get just inside me and I sighed and moved my ass back, getting more of him in me. It hurt a bit, but Matt took it loose and slow at outset, 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 go away me the fuck alone. Now lustrelessness was fucking me and I was in heaven. I felt his cock microscope slide oceanic abyss in me and take me up. It turned me on in ways I'd never have expected.

Matt slid his peter in me so far, I could almost palpate him jab my abdomen. I'd almost swear I saw my corporation bulge as he got all the way in. In maliciousness of whatever reservations I'd had, I was loving every second of this, every stroke of his stopcock. I wanted his shaft in my ass, and when he came with a outpouring in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our sides, with his prick still inside me. I was on a sexual high and wanted nothing more than to keep feeling his cock in my ass. His prick was getting gentle, but I wanted to retain him in me as long as I could. As we came off our heights, matte began to stroke my shoulder joint and kiss the back and face of my neck.

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

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

"I just might go for you to that, Lynn, baby."

Essentially, matt was spooning me as we lay there in his bed with his cock slowly easing its way out of me. I moved my ass back, trying to maintain as a good deal of him in me for as recollective as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the next dawning 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 toilsome cock against my ass, I'd have leapt from bed and gotten out of the elbow room as fast as I could. Instead, I moaned and moved my ass around against his prick.

Matt woke up and began stroking me and kissing the backbone of my neck as he eased around so his cock was up against my arse. I could sense it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our face. It was a gentler screw, instead of the pounding that we had at the end last night, but I still loved it.

My peter got backbreaking as I felt his filling me up. It was a slow leisurely piece of ass, 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 stopping point nighttime, and for this morning too."

"I hope we'll have more than just last dark and this morning."

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

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

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

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

"What happens to Lenny ?"

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

By then, lusterlessness's dick had slipped out of my ass and I'd rolled over face matte. I kissed Matt, and he kissed me back and began stroking my trunk. We spent a yearn time petting and touching each other before we got up and went to the exhibitioner together. Without my clothes, my bra, my pantie, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his dick, I got down on my knee joint and sucked him off again. With my physical composition off and hair wet, I didn't look quite the Same, but I dried my hair, styled it as best I could and got dressed in my clothes from shoemaker's last night. I had a trivial makeup in my purse and could do lipstick, eyeliner and a lilliputian al-Qaida, to make me more like Lynn.

The more I looked like Lynn, the more than Matt seemed to be affectionate. He fucked me once more before taking me home, and we made a date for that eve.

When I got home, I looked at myself in the mirror, then just slumped onto the couch and shook my straits. I could find 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 to the lowest degree, I guess I was Lynn, until flatness got tired of me or I got tired of it all. I opine Karen's supernumerary wearing apparel were now Lynn's clothes till further notice.

Matt took me out again Sat night, and took me back to his piazza. We were not as tired or drunk and after I went down on him, he fucked me three multiplication. I enjoyed it but as I drifted off to sleep, I was starting to sense contravene. Was this really how I wanted to live out my life ? And how retentive was lusterlessness probable to be interested in me ?

We fucked a couple more meter the adjacent sunrise and I went base. I decided that Lynn would only be on Fri and Sat Night. I was going to live and mould as Lenny, the rest of the meter. It was hard. We all want to be appreciated. We all want mortal to think we are special. Lenny is n't especial to anyone, though Lynn is.

Occasionally during the calendar week, I would be Lenny and go out as Matt 's wingman. flatness always found an attractive cleaning lady to take aim home. I was a piffling jealous - both of matte and of the womanhood. On rarified occasions, I 'd be Lynn during the calendar week, and Matt would come to my place to fuck me. Usually Lynn was a weekend thing, but some weekends, Matt had other plans.

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

One Friday nighttime, matt and I were at a order and I was being Lynn, though Matt seemed to be giving almost of his attention to a very jolly blonde. I sat there feeling pretty neglected, when Nicole came up to talk to me. Nicole was a brunette, about my age, a bit taller, but with a very nice shape, b-cup boob, and a pretty face.

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

'' I guess I 'm old intelligence. ``

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

'' Hi, Nicole. I 'm Lynn. And lustrelessness and I have kind of an strange relationship. ``

'' wellspring, your guy appears to be about ready to maltreat out with another woman. Would you have any sake in doing the same ? Or are you strictly into guys ? ``

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

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

'' What do you imply by straddling the logical argument, Nicole ? ``

Nicole reached up, and stroked my facial expression. I 'd shaved as cleanly as I could before going out with Matt, and my seventh cranial nerve hair is not heavyset, but there was the svelte trace of very light shuck and I could severalise by her expression that she felt it. Nicole leaned forward and kissed me.

'' well, Lynn, something tells me that you straddle the line. ``

'' And you like that ? ``

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

'' I like woman, I 'm just ... ''

Nicole took my hand and led me out onto the dance floor. I glanced back at Matt and he was so fixated on the blonde that he never even noticed that I left. We did a mates of degraded dances, and I really enjoyed dancing with Nicole. Hell, as Lenny, I had trouble getting char to level trip the light fantastic much with me.

A slow number came on and Nicole grabbed me and pulled me close. She put one hired hand in the middle of my back and the other one down over my ass. I giggled and squirmed as she caressed my ass through the dancing. I glanced around and no one seemed to even remark us or what we were doing.

At the end of the dance, Nicole gave me a osculation that almost buckled my genu. I could feel my hawkshaw getting hard and barely being restrained by my pantie. My idea was blown. We stood there kissing for I'm not even sure enough how long. I'd never had a cleaning woman kiss me like that before, and I was in no rush for it to end.

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

"Well, Lynn dear, it looks like you lost your guy."

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

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

I leaned forward and kissed Nicole, and she returned my kiss. We finished our drinks, danced a bit more then Nicole invited me back to her place. Nicole was an inside sales rep for a tech society. She worked near where I did and made some decent money. I was still amazed that she had any sake in the the likes of 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 possess some fun."

"I like daughter, I just never had much fortune before."

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

I felt a picayune uncertain. Nicole was pretty and she seemed bequeath. I just didn't understand why she'd have any interest in me - not after knowing that I was a guy dressed as a daughter who'd been out with a guy. Look, I'd never had any cleaning lady willing to establish me the meter of day, much less get intimate with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

mat had left me and gone off. I could either promise an Uber or find out what Nicole had in mind. Honestly it was probably better than what Matt had done, even though I seemed to enjoy fucking Matt. I sat for several bit, just pondering the possible action. I looked at Nicole who sat there with a lilliputian oracular smile on her brass, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walk on the raging side 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 nightspot. She had a car nearby, nada as expensive or flashy as Matt's BMW, but a Nissan 370Z a dyad 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 Saami, but Nicole was a woman and knew what I was down below.

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

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

"Best go I've had in a longsighted time."

"bettor than your piffling boyfriend ?"

"No question."

We were stopped, getting ready to cash in one's chips the parking lot. I leaned over and gave Nicole a kiss. She smiled and stroked my head, before taking us out on the road. She drove us a few miles to her apartment. It was on the second storey and we had to walk a flight of steps of stair, but we had our coat of arms around each other, giggling and petting each other as we went.

Nicole had a prissy little one bedchamber office, clearly feminine, with a damp floral couch and chair, along with some art photographic print on the paries. The prints were largely of women and men, along with a few where it wasn't quite clear if it was male or female. She walked me over and we sat on the sofa, and she put her arm around me.

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

"I really just started dressing up in my sis's dress as a turn-on. I told lustrelessness one time when I was wino and he wanted me to garb 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 solely 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 family 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 imagine about guys."

"wellspring, I like Lynn, and I might even like Lenny. How do you feel about that ?"

"I'd love that, Nicole."

"And if I want you to be Lynn for me, at least some of the time ?"

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

"What about your footling boyfriend Matt ?"

"I think he's getting a little pall 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 belated tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the tenacious prison term. I wanted more of track, but I didn't want to rush things and upset her and maybe make her send me on my way. Nicole stroked my trunk, mostly back, arms, and ass, so I followed her wind and did the same to her. After a farseeing stretch of kissing and touching, Nicole stopped.

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

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

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

My bra, of course, was filled with cushioning, 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 organic structure. She had both hands on what would own been my tit, if I had any, so I placed my other hand on her other breast.

I was a little bear on about pushing it too far, but Nicole seemed to get even more turned on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the unity 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 declivity 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 cushioning fell to the storey, leaving my bare chest out there. I got my first look at Nicole's breasts - actually the number 1 breast I'd ever seen be and in person. I wanted to tinct them but I was hesitant. I didn't want to move too fast and spoil affair. Again Nicole put my handwriting on one of her boob, then began to stroke my monotonic, boobless, chest.

Her boobs felt amazing, warm, voiced, and just so wonderful. I began to caress her tit and nipples as Nicole played with my chest. After a footling spell, she stopped kissing me and guided my mouth down to one of her luscious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the breast right on her nipple.

Nicole leaned back, pulling me with her as I began to kiss and solve her breast all over. Her nipple got very hard and stood out farther than I realized they even could. Not only was I reveling in this, her bosom seemed to revel in my attention. After a bit, she shifted my mind over to the former pinhead, and I began to give it the same aid that I'd been giving its partner.

I spent a long clip 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 out me on my way. Instead Nicole stood and pulled me to my pes and led me by the hand into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, sister, unzip my skirt."

I unzipped her and she let the skirt slide down her body onto the story. She stepped out of the dame, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet pip in the front line of them, as Nicole unzipped my skirt. My panties were having fuss restraining my tool, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

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

"Anything you want, Nicole."

"commencement, charter off my panties."

I moved down her body and Nicole lifted her hips off the bed. I slid her scanty down and once they were clear of her ass, she dropped her hips back to the bed and lifted her human foot, letting me take them completely off her. Nicole spread her leg and for the first time I got to see a woman's pussy. Nicole had shaved near of it, except for a narrow striptease just above her labia. Nicole gently pulled my head to her chthonian part, though I had no idea what I was supposed to do.

"Okay, baby. Kiss it, lick it, stick that clapper in me."

Nicole directed me as I ate her out, until she wrapped her ramification around my head, almost crushing me, while humping my rima oris and moaning. My nerve was wet with her juice as she released me, then pulled me back up to snog me. We kissed for a spell, until she rolled me over and got on top of me. She lifted up on my hips, so I raised them off the bed, and she pulled off my panties.

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

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

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

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

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

Nicole began moving her hips taking my prick 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 much sentence jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her bosom and fondled her ass. After a while, I realized I was getting close.

"I'm going to cum, Nicole."

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

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

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

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

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

"What do you mean."

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

Nicole eased the thing into my ass, until I was well-situated with it, then began to slowly have a go at it my ass with this strap-on. I wasn't sure I wanted her to do that, but at this period, I wasn't going to argue with her. As she began fucking me, I began to get into it. For obvious reasons, she was able to celebrate going a lot longer than Matt even could, and my cock got hard again, and I came on the bed.

With that, she stopped and eased it out of my ass, then turned me over and kissed me some more. She kept the twist on her even through that. We kissed for a long time before she turned me on my English and spooned me, with her strap-on press 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 forenoon, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me fuck her pussy. We showered together, playing as we washed each early. 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 specific, but I'd passion to pass it with you, if you're available."

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

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

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

"Not as long as I can spend my clip 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 flat and sat on the couch, just amazed at the cobbler's last 24 minute. While I sat there, my phone rang - a call from Matt.

"Hey, babe. Sorry I left you final 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 home base or you'd catch an Uber or something."

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

"So she was sang-froid 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 work with."

"You're spicy than Toni."

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

"Come on, girl. If it weren't for me, you'd have had no sex life and no chance at that Nicole."

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

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

"She's all lady friend, but she's got devices. I'm not missing out on anything, and I'm getting affair I could never get with you. I get to play with dummy, I get to get it on a pussy."

"Are you fucking dumping me, bitch ?"

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

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

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

"I give it two weeks at the outside."

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

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

"Just call back, if you out me as a cross dressing table, you also out yourself as fucking a guy who cross apparel. Your little girl might not train that very well."

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

"And you've gotten requital for that. And if or when Nicole ditch me, if you aren't too big a beef, you might even get more. In the meantime, I hope you have a great evening."

So who was I ? Who did I want to be ? Matt only wanted me as Lynn, and it was starting to look like Nicole did too. The 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 bisexual enough to get off on what I did with Matt, but why give up on woman if I had any probability with them ? I was still sitting there in clothes as Lynn, when there was a knock on the doorway. I was puzzled, because I wasn't expecting Nicole, matte, or anyone else for some time. I was a piffling leery of opening the doorway, when it was unlocked from outside.

I sat there shocked as my sister Karenic came in the apartment. She didn't situation me immediately, but turned to close and lock the door. She saw me and her mouth hung open and she seemed freeze down 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 nooky ?"

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

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

"You're obviously in my clothes."

"Yes. It's variety of a farseeing story."

"Are you wearing my pantie and bras too ?"

"I am."

"I got a bigger place 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 Thomas More stuff."

"So is dressing like this what makes you well-chosen ?"

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

"A missy ? A real female child ? Not some in between or falsify affair ?"

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

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

I looked at my shoes. I couldn't looking at Karen in the face. She understood immediately.

"nookie. 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 fair sex, you'll go back to fucking guys ?"

"Karen, please."

"Lenny, it's your life. Fuck who you want. Just don't show up at household or my plaza dressed like that."

I was crying by this fourth dimension. 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 remain to be Lynn. I wept on Karenic's shoulder, and she took some compassion on me and stroked my head and tried to soothe me. It took a while before I regained my composure.

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

"I hope you can understand and forgive me."

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

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

"So you dressed this way to get guys ?"

"I just dressed like this to get myself off, until a guy I knew saw me. He liked what he saw, and while I wasn't completely comfortable, it was better than being alone."

"And this daughter you're with now ?"

"Saw me, liked me, and figured out what I was. She liked women and men and seemed well-chosen with me dressed like this."

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

"I don't know how long it'll hold up, but I'll do what I have to do to hold on 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 outwear any of the clothes I left here, so they're all yours."

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