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

It was a bit inconvenient, since I just had a one bedroom office, and not all that big. Being a nice little comrade, I let her let the bed, while I slept on the couch. She had a ton of clothes and more than filled my closet, leaving little way for my clothes. Beyond that, we had to share one tiny toilet, in shifts, 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 calendar month before getting her own place and moving out. Her place was smaller than mine, so while she took nigh of her stuff, she had more clothes than she had elbow room for in the new place. She didn't want to donate them, so she asked if she could leave them at my place until she could yield a bigger shoes. Again, being a overnice buddy, I let her do it.

Karen left behind all manner of things, skirts, frock, blouses, brassiere, panties, skid, makeup, and all that. After I while I got fascinated with it, which I guess was my foremost misapprehension. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.

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

As time went on, I'd dress up completely in Karen's clothes for my self-stimulation Roger Sessions, and even left them on after I'd cum. I began to play with it all a short bit and even began to use some of the makeup she'd left behind. I'd pad her bras with socks or whatever, put on panties, a skirt, blouse, and shoe, then brush my haircloth in a more womanly style and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no missy willing to assist me. Before recollective, I'd come plate from work, plume up all girly, and prance around my apartment before getting myself off. I'd even wear one of Karen's old nighties to bed afterward.

I had a few friend who I'd hang out with occasionally. One of them, who I'd known since high school was lustrelessness. He was always the democratic sort, never had any problem getting fille, and often seemed to birth one or Sir Thomas More hanging off him. He'd have me along as a wingman sometimes, though I never managed to get any miss out of it.

One dark he and I were drinking, and I'd had more than I should have got, and we began talking. He started telling me about how he got some skirt to let him finger her in populace in a restaurant. He said they'd also gone to a pic theater, sat way in back, and she hiked up her skirt, sat on his lap, and fucked him in the dramatic art during the movie.

"Hey, Lenny, what's the nappy thing you've even done ?"

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

"seed 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 apparel to jerk off.

"Seriously, Len. Do you just drop off on her pantie to get turned on or do something More ?"

"Sometimes I'll go wide-cut retarding force, clothes, brake shoe, makeup, and everything."

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

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

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

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

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

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

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

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

…………………………………………………………………………

The next day I really had some sorrow about agreeing to let him see me dressed up. I called him during lunch and tried to second out, but he said I'd promised and he expected me to keep my promise. I was on boundary all afternoon. I got home about six and took off all my dress. I swear I was shaking as I cleaned up, showered with scented consistence wash, shaved my face, stage, 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 babe's dress. I dried my hair and styled it girlish, then put on scanty, a bra, a nice bird, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye shadow, lipstick, and of course I painted my toenails and fingernails.

I wore some low hound with open toes, to demo off the toenail Polish and looked at myself in the mirror. I knew I was a guy in pull, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the bell rang at seven o'clock. My knees were wobbly as I walked to the door. I looked through the peephole and sure enough it was Matt. I opened the door and let him in.

mat was gaping and staring as he walked in my shoes. I closed and locked the doorway 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 tomentum 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 damn, 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, lusterlessness, you got to see me, now let me alter back."

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

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

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

"This was a misunderstanding. 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 practically pleasure out of this.

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

"Matt, this flavour really weird."

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

"You've got caboodle of girls - real young lady, not fake ones, like me."

"Don't shoot down yourself down. nigh of those girls have nothing on you."

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

"Let me get you out to dinner, Lynn"

"Just let me change into some rule apparel, Matt."

"No, babe, just like this."

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

"Sure you can, cocker. 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 world with a guy in puff ?"

"No one but you and I will get it on, and besides I like a little bit of kinky sometimes."

"I don't know."

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

"That makes me feel really weird."

"And maybe a fiddling 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 animal foot. He wrapped his implements of war around me and pulled me shut. I think my eyes were the size of saucers and my human knee were getting weak as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the room access. When we got there, he stopped and turned.

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

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

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

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

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

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

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

He used valet parking and walked me in, holding the door for me. I still felt unearthly as turd, but just tried to ignore how I looked and enjoy myself. lustrelessness ordered a nice feeding bottle of wine for us, and I really needed something to drink. I downed my firstly Methedrine before he'd taken more than a distich sips of his wine. matte poured me another glass, but I took it a slight slower.

The waiter seemed very taken with me, and when he thought I didn't card, tried looking down my blouse. Several other men seemed to find me, which made me squirm in my buns. One guy who works with mat stopped at the mesa to blab with us. I'd met him several prison term before, but he clearly didn't recognize me.

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

"This is my date, Lynn. Lynn, meet Joseph Oliver, he ‘ s another department handler where I work."

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

"And I'm very pleased to suffer you, Lynn. flatness is clearly a very lucky man. But if you want a change of scenery, give me a birdcall, I'd love to bear witness you a good time."

With that, Oliver handed me a line of work card. I think I turned red, but slipped it in my purse.

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

"Well, lusterlessness, if you get tired of Lynn here, feel rid to send her my way."

Oliver bent down and kissed my buttock before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot chick. Half the men in this place would dump their engagement for a chance to look at you home."

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

We had a lovely dinner and I continued to drink way more than I should receive. This whole shot had blown my mind so much I didn't know what else to do. A few early men stopped to blab out to us. They invariably seemed to pay unreasonable attention to me, when they stopped to talk to matt. We finished dinner and I thought Matt would take me back to my place.

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

"Are you sure about that ?"

"You're taking a walk on the groundless side, just engage a bit longer walk."

Matt wouldn't take ‘ no'for an answer and drove us to the hottest club in townsfolk. This was the sort of seat that would never let the likes of me inside. They must have had a hundred people lined up waiting to get in. matt was obviously pretty well known, and he walked us up to the presence, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a drink and then matte wanted to dance with me. I felt unusual as shit, but it was a fast number and I was already half plastered so I went out to dance with him. We danced several fast dances, then a boring number came on. I thought we'd go sit down, but instead, Matt pulled me close to him to dance.

He had one paw on my speed back, holding me taut, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that Matt had a erection as he did that. That scared me more than a petty, but I wasn't for certain what I could do. I felt helpless as we danced. When the issue ended, Matt stopped, held me tight, and kissed me.

My genu got so infirm that if he hadn't been holding me compressed, I'd probably have slumped onto the floor. He gave me a hanker kiss, and to my surprise, I began to buss him back. I felt contravene - 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 of arc before he walked me back and we had another drink.

I'd been drinking pretty good before, but I didn't retard down. I was half afraid of what was going to happen, and felt like I needed to be very booze. We drank more and danced to a greater extent, and the more we drank and danced, the more Matt kept feeling me up and kissing me. My psyche was blown - matte knew I was a guy dressed like a adult female, yet he was acting like I was the real thing.

As I said, I'd been lustrelessness's wingman more than a few times, and had seen him this way with woman many clock time before. I also knew that in most cases he ended up taking those charwoman home and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don't know how long we danced and drank, but by the sentence Matt was ready to leave, I was really plastered.

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

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

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

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

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

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

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

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

"What… What did you want me to do ?"

"If zip 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 former hand. He pulled out his cock, which was already firmly and standing straight up. He kissed me again, then gently pushed my question down toward his cocksucker. I got conclude 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 head of his dick between my lips.

lustrelessness moaned and leaned back, still keeping a hand on my head. I let the head of his cock slip from between my lip, before taking it back and going just a fiddling farther with it. I bobbed up and down on his son of a bitch, gradually taking it deeper and cryptic into my mouth. I'd never had a dick in my mouth before and it felt unusual, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my mouth and matt seemed to like it. Some precum came from the tip, and it had a salty predilection, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the base of his dick as I sucked the rest of it. By now, Matt was moving his pelvic arch, almost fucking my mouth, as he held my top dog tight.

lusterlessness moaned loudly and got very set as his cock erupted in my oral fissure. He held my head with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for breath, 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 teacher back from it.

lustrelessness pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my mouth as we kissed, but that didn't seem to nettle him. flatness continued to kiss me and I didn't even make 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 panties and fondled my bare ass.

I don't know why I didn't observance, I don't know why I didn't stopover him. Maybe I was enjoying it all too lots, and maybe I was just too fuddle. Before I even realized it, flatness had removed my dame and blouse and was carrying me into his sleeping accommodation. I was so far gone at this head I didn't know or care, or maybe it was what I really wanted.

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

"Do it, lustrelessness. Do it."

lusterlessness set me down on his bed on my workforce and human knee and pulled down my panty. My peter, which had been ignored for so farseeing sprang to care, but Matt was interested in other matter. He took off his gasp and shirt and got in bed behind me. He reached into a draftsman in the table beside the bed and got a underground of lube.

lusterlessness rubbed lube over his scratch, 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 moment or two. He snuck a second fingerbreadth in and began to finger fuck my ass, and in malice of myself, I began to fuck him back. Matt leaned down and kissed the back of my neck opening as he pulled his finger's breadth out of my ass.

I felt the forefront of his stopcock at my asshole and tensed for just a arcsecond before relaxing. At this head, I think I wanted him as much as he wanted me. I felt the psyche 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 easy and slow up at get-go, until I really started to get into it.

I soon felt his hips slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy fuck my ass, I'd have thought you were demented and told you to leave me the fuck alone. Now Matt was fucking me and I was in heaven. I felt his dick microscope slide deep in me and fill me up. It turned me on in path I'd never have expected.

Matt slid his dick in me so far, I could almost feel him jab my stomach. I'd almost swear I saw my breadbasket bump as he got all the way in. In spite of whatever reserve I'd had, I was loving every second of this, every stroke of his cock. I wanted his prick in my ass, and when he came with a outpouring in me, I came right onto his bed.

flatness collapsed onto me and I collapsed and we rolled onto our side of meat, with his prick still inside me. I was on a intimate high and wanted nothing more than to prevent feeling his cock in my ass. His dick was getting voiced, but I wanted to stay fresh him in me as long as I could. As we came off our high, flatness began to stroke my articulatio humeri and osculate the back and side of my neck.

"Lynn, babe, you are beautiful, aphrodisiac, and howling, and I just wish I could stay on inside you forever."

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

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

Essentially, flatness 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 keep as a good deal of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the side by side morning with flatness 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 unvoiced peter 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.

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

My dick got intemperately as I felt his filling me up. It was a slow leisurely shtup, almost loving, and I reached behind me to stroke lusterlessness's soundbox 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 sunrise too."

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

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

"I want it. I want your shaft in my ass, in my mouthpiece, wherever you want, and whenever you want."

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

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

"What happens to Lenny ?"

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

By then, Matt's prick had slipped out of my ass and I'd rolled over facing matte. I kissed lusterlessness, and he kissed me back and began stroking my organic structure. We spent a longsighted prison term necking and touching each other before we got up and went to the shower together. Without my dress, my bra, my panties, I looked more like Lenny, but we washed each early, continuing to kiss.

After we washed off his rooster, I got down on my knees and sucked him off again. With my constitution off and haircloth wet, I didn't smell quite the same, but I dried my hair, styled it as best I could and got dressed in my clothes from utmost night. I had a little makeup in my bag and could do lipstick, eyeliner and a picayune theme, to piss me more like Lynn.

The more I looked like Lynn, the to a greater extent Matt seemed to be fond. He fucked me once more before taking me menage, and we made a engagement for that eventide.

When I got household, I looked at myself in the mirror, then just slumped onto the couch and shook my promontory. 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 lusterlessness got tired of me or I got tired of it all. I guess Karen's spear carrier clothes were now Lynn's clothes till further notice.

flatness took me out again Saturday night, and took me back to his space. We were not as tired or sot 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 feel conflicted. Was this really how I wanted to live out my aliveness ? And how hanker was matte in all probability to be interested in me ?

We fucked a couple more meter the next morning and I went household. I decided that Lynn would only be on Friday and Sabbatum Night. I was going to live and act upon as Lenny, the eternal rest of the clip. It was hard. We all want to be appreciated. We all want somebody to think we are special. Lenny is n't special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as Matt 's wingman. matte always found an attractive woman to take home. I was a little jealous - both of lusterlessness and of the woman. On rare occasions, I 'd be Lynn during the hebdomad, and Matt would come to my post to fuck me. Usually Lynn was a weekend thing, but some weekends, matt had other plans.

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

One Friday night, lustrelessness and I were at a club and I was being Lynn, though Matt seemed to be giving most of his care to a very moderately blonde. I sat there feeling pretty neglected, when Nicole came up to utter to me. Nicole was a brunet, about my age, a bit taller, but with a very nice shape, b-cup boobs, and a pretty face.

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

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

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

'' Hi, Nicole. I 'm Lynn. And lusterlessness and I have kind of an unusual kinship. ``

'' fountainhead, your guy appears to be about set to ill-use out with another woman. Would you induce any interest in doing the same ? Or are you strictly into Guy ? ``

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

'' I like cleaning woman. I like men. And sometimes I straddle the occupation. ``

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

Nicole reached up, and stroked my grimace. I 'd shaved as cleanly as I could before going out with lustrelessness, and my nervus facialis hair is not thick, but there was the slightest trace of very low-cal stubble and I could tell by her locution that she felt it. Nicole leaned forward and kissed me.

'' Well, Lynn, something tells me that you straddle the note. ``

'' And you like that ? ``

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

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

Nicole took my manus and led me out onto the dancing floor. I glanced back at Matt and he was so fixated on the blonde that he never even noticed that I left. We did a couple of fast dances, and I really enjoyed dancing with Nicole. Hell, as Lenny, I had difficulty getting women to even dance a great deal with me.

A slow number came on and Nicole grabbed me and pulled me end. 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 notice us or what we were doing.

At the end of the dance, Nicole gave me a buss that almost buckled my human knee. I could find my hawkshaw getting harder and barely being restrained by my panties. My mind was blown. We stood there kissing for I'm not even for sure how long. I'd never had a woman kiss me like that before, and I was in no rushing for it to end.

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

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

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

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

I leaned forward and kissed Nicole, and she returned my osculation. We finished our beverage, danced a bit more then Nicole invited me back to her topographic point. Nicole was an inside sales rep for a tech company. She worked near where I did and made some decent money. I was still amazed that she had any pursuit in the like of me.

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

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

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

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

I felt a picayune uncertain. Nicole was pretty and she seemed unforced. I just didn't understand why she'd have any interestingness in me - not after knowing that I was a guy dressed as a girl who'd been out with a guy. flavour, I'd never had any woman willing to give me the time of day, much less get intimate with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

Matt had left me and gone off. I could either call an Uber or incur out what Nicole had in creative thinker. Honestly it was probably better than what Matt had done, even though I seemed to relish fucking Matt. I sat for several seconds, just pondering the possible action. I looked at Nicole who sat there with a little oracular smile on her face, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

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

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the club. She had a car nearby, nothing as expensive or flashy as lusterlessness's BMW, but a Nissan 370Z a match of twelvemonth old. It was certainly nicer than my eight year old Civic. Nicole opened the car doorway for me, which surprised me a bit. Yes, lusterlessness had been doing the like, but Nicole was a woman and knew what I was down below.

I stood slightly puzzled for a instant before smiling at her and sitting down in a ladylike mode. Before she closed the car door, Nicole leaned over and kissed me. She came around, sat down in the number one wood's seat and started the car. Before she put it in gear, she smiled at me again and gave me a agile kiss.

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

"topper offer I've had in a long time."

"punter than your little beau ?"

"No question."

We were stopped, getting ready to exit the parking lot. I leaned over and gave Nicole a osculation. She smiled and stroked my head, before taking us out on the road. She drove us a few Swedish mile to her flat. It was on the back floor and we had to walk a flight of stairs, but we had our arms around each other, giggling and petting each other as we went.

Nicole had a nice lilliputian one sleeping room place, clearly feminine, with a muted floral couch and chairwoman, along with some art prints on the walls. The prints were largely of women and men, along with a few where it wasn't quite unmortgaged 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 sister's clothes as a turn-on. I told matte one time when I was drunk and he wanted me to raiment up for him."

"Obviously, you did."

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

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

"Oh my God, no. Even now, the only prison term I go out this way is with him."

"But you were into guys ?"

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

"rich person you been with any other Guy than him ?"

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

"Well, I like Lynn, and I might even care Lenny. How do you sense about that ?"

"I'd lovemaking 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 matte ?"

"I think he's getting a piffling outwear of me."

"What if he isn't ?"

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

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

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the longest metre. I wanted more than of course, but I didn't want to rush affair and swage her and maybe make her send me on my way. Nicole stroked my consistence, mostly back, blazon, and ass, so I followed her pencil lead and did the Saami to her. After a yearn stretch 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 unwrap the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her chick, and she asked me to draw in it loose and take it off her. She sat there with only her bra on the upper berth half of her soundbox. I hardly even noticed as she took my blouse off me.

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

My bra, of course, 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 cushioning, it still sent a shudder of pleasure through my trunk. She had both hands on what would have been my boobs, if I had any, so I placed my early hand on her former breast.

I was a picayune concerned about pushing it too far, but Nicole seemed to get even more move around on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the ones I wore for some meter, but never messed with anyone else's bra. I reached behind her and fumbled a bit before getting it unhooked.

I rubbed her back where the bra had been, and Nicole moaned and squirmed, then shrugged, which let the bra fall forward. She had her implements of war 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 spell before she leaned back to allow our bras to fall off each of us.

My bra and padding fell to the level, leaving my bare thorax out there. I got my first flavor at Nicole's white meat - actually the low breasts I'd ever seen unrecorded and in person. I wanted to touch them but I was hesitant. I didn't want to actuate too fast and screw up things. Again Nicole put my hand on one of her dummy, then began to stroke my flat, boobless, chest.

Her dope felt amazing, lovesome, soft, and just so wonderful. I began to caress her pinhead and tit as Nicole played with my dresser. After a little spell, she stopped kissing me and guided my mouth down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the tit right field on her nipple.

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

I spent a long sentence hugging and pleasing her knocker, before Nicole clutched my forefront tightly to her as she moaned and writhed on the sofa. As it settled back down again, she pulled me back up and kissed me before sitting us both up. I was afraid that she was indicating that we were done and was going to ship me on my way. Instead Nicole stood and pulled me to my understructure 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 annulus slide down her eubstance onto the flooring. She stepped out of the skirt, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet point in the movement of them, as Nicole unzipped my skirt. My scanty were having trouble restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

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

"Anything you want, Nicole."

"First, take off my panties."

I moved down her torso and Nicole lifted her rose hip off the bed. I slid her pantie down and once they were clear of her ass, she dropped her hips back to the bed and lifted her animal foot, letting me take them completely off her. Nicole spread her wooden leg and for the number 1 meter I got to see a charwoman's slit. Nicole had shaved most of it, except for a narrow flight strip just above her labia. Nicole gently pulled my mind to her nether regions, though I had no mind what I was supposed to do.

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

Nicole directed me as I ate her out, until she wrapped her legs around my headspring, almost crushing me, while humping my back talk 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 patch, 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 makeup as Lynn, even if I basically looked like Lenny from the neck opening down. As she pulled my panties off, she kissed the oral sex of my pricking, which was as backbreaking as I've ever seen it. Look, I'm no great trill in that department, but I've got about six inch, and it was in its full moon resplendence as Nicole slid back up my body.

I could palpate my pecker, sawing between her thighs, even rubbing across her puss back talk as Nicole writhed around on me. Finally, she lifted her hips, grabbed my cock and guided it into her sweet pussy. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was 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 conceive you like this ?"

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

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

Nicole began moving her pelvis taking my putz nearly out of her, then deeply in again. I was in heaven, and wished it could never end, even if I knew she was correctly. I'd spent so much meter jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her dumbbell and fondled her ass. After a spell, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it baby, redress inside me. fill me up with it."

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

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

"That was tremendous. near than anything I've ever done with Matt."

"We don't want you to drop 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 dick. She had me get on handwriting and knees, then got some lubricating substance from a nearby draftsman, before lubing up the penis and my ass.

Nicole eased the thing into my ass, until I was well-heeled with it, then began to slowly get it on my ass with this strap-on. I wasn't sure I wanted her to do that, but at this point, I wasn't going to fence with her. As she began fucking me, I began to get into it. For obvious ground, she was able to restrain going a lot recollective than Matt even could, and my tool got hard again, and I came on the bed.

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

………………………………………………………………………………..

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

"So, did you have any architectural plan for tonight, Lynn ?"

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

"That sounds bully. I've got some errands and affair to do this afternoon, so you need to get your cunning petty ass dwelling house, 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 job with that ?"

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

"That's my female child. Now get dressed and scoot."

I put my apparel 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 hour. While I sat there, my telephone set rang - a Call from Matt.

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

"That was Nicole. We were enjoying ourselves."

"I figured either she'd sacrifice you a lift rest home or you'd collar an Uber or something."

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

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

"Yeah, she was."

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

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

"You're hotter than Toni."

"Maybe you should stimulate 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 fortune at that Nicole."

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

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

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

"Are you fucking dumping me, bitch ?"

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

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

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

"I give it two week at the outside."

"Well then, I'll take that two weeks. In the interim, you have Toni or one of the early 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 crossing dresser, you also out yourself as fucking a guy who cross wearing apparel. Your picayune girlfriends might not take that very well."

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

"And you've make requital for that. And if or when Nicole underprice me, if you aren't too big a beef, you might even get to a greater extent. In the lag, I hope you have a great evening."

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

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

I sat there shocked as my sister Karen came in the apartment. She didn't spot me immediately, but turned to fill up and engage the door. She saw me and her rima oris hung open and she seemed frozen in position until she began moving slowly toward me. Karenic got over to me, reached out a hand and touched my face.

"Lenny ? What the fuck ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my scanty and bras too ?"

"I am."

"I got a bigger place and was going to plunk up the rest of my dress, but if you've been wearing them, I don't think I want them anymore."

"I'm sorry. I'll pay you back, or buy you More stuff."

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

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

"A lady friend ? A real little girl ? Not some in between or bull thing ?"

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

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

I looked at my place. I couldn't tone Karen in the face. She understood immediately.

"Fuck. You mean you did that too ?"

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

"But if she dumps you and you can't get hold another woman, you'll go back to fucking guys ?"

"Karenic, please."

"Lenny, it's your liveliness. nooky who you want. Just don't show up at home plate or my place dressed like that."

I was crying by this clip. Karen made me ashamed of what I'd done and what I'd become. At the same metre, I needed roll in the hay too, and if being Lynn was what kept Nicole then I was going to continue to be Lynn. I wept on Karen's shoulder joint, and she took some compassion on me and stroked my mind and tried to soothe me. It took a patch before I regained my composure.

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

"I hope you can empathize and forgive me."

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

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

"So you dressed this way to get Guy ?"

"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-to-do, it was better than being alone."

"And this missy you're with now ?"

"Saw me, liked me, and figured out what I was. She liked womanhood 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 know how long it'll finis, but I'll do what I have to do to hold on it going."

"Should I still holler 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 out any of the clothes I left here, so they're all yours."

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