It started kind of strange. I am or at least was Len or Lenny - Elmore John Leonard to my mother - a guy in my early 20s, kind of suddenly and slender. I had a sister, Karenic who was a few eld older than me. She'd had a smutty dissolution with a fiancé, and stayed with me for a while when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one chamber place, and not all that big. Being a nice little brother, I let her give the bed, while I slept on the couch. She had a ton of clothes and Sir Thomas More than filled my closet, leaving little room for my clothes. Beyond that, we had to ploughshare one tiny john, in switch, since there was no way we were going to be in there at the same time - too humble and too weird.

Karen stayed with me for about six months before getting her own place and moving out. Her topographic point was smaller than mine, so while she took most of her stuff, she had more clothes than she had way for in the new lieu. She didn't want to donate them, so she asked if she could exit them at my place until she could afford a with child place. Again, being a nice brother, I let her do it.

Karen left behind all style of thing, bird, attire, blouses, bras, panties, shoes, war paint, and all that. After I while I got fascinated with it, which I surmisal was my first misunderstanding. I started by just touching some of the clothes. I was a middling nerdy guy who could never get anywhere with woman, 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 promontory while doing myself. After a prison term, that didn't turn me on the way it once did, so I even began putting on some of her wearing apparel. That seemed to be a bigger turn-on and her wearing apparel seemed to fit, since we were almost the same size.

As sentence went on, I'd dress up completely in Karenic's clothes for my self-abuse school term, and even left them on after I'd cum. I began to play with it all a little bit and even began to use some of the makeup she'd left behind. I'd pad her brassiere with socks or whatever, put on panties, a chick, blouse, and shoes, then brush my hair in a more feminine flair and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as parting of self-stimulation. blaze, I needed to get off too, and there were no girls willing to facilitate me. Before long, I'd come home from body of work, dress up all girly, and swagger around my apartment before getting myself off. I'd even wear one of Karenic's old nighties to bed afterward.

I had a few friends who I'd hang out with occasionally. One of them, who I'd known since gamy schoolhouse was mat. He was always the popular sort, never had any problem getting girlfriend, and often seemed to have one or Sir Thomas 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 more than I should birth, and we began talking. He started telling me about how he got some doll to let him feel her in world in a restaurant. He said they'd also gone to a movie theater, sat way in back, and she hiked up her skirt, sat on his lap, and fucked him in the field of operations during the movie.

"Hey, Lenny, what's the way-out thing you've even done ?"

"Shit, flatness, I can't get missy to do ordinary prick with me, much less anything kinky."

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

As I said, I'd had too a great deal to drink, and I confessed to dressing up in my sister's clothes to jerk off.

"Seriously, Len. Do you just slip on her panties to get turned on or do something more than ?"

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

"shag, 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 own someone see me."

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

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

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

That was Thursday, and it was already late and I was too drunk and had to sour the next day. He asked if I'd coif up for him the next night. I agreed and told him to come by after work on Friday, but to give way me some time to get ready.

"Lenny, do you cogitate you can be make in an hr ?"

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

…………………………………………………………………………

The following day I really had some regrets about agreeing to let him see me dressed up. I called him during tiffin and tried to second out, but he said I'd promised and he expected me to save my promise. I was on edge all good afternoon. I got domicile about six and took off all my apparel. I swear I was shaking as I cleaned up, showered with scented soundbox race, shaved my font, legs, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the opinion of having this guy see me in my Sister's clothes. I dried my hair and styled it girlish, then put on panties, a bra, a nice annulus, and a blouse, then sat down to do constitution. By now I had it almost to a science, putting on base, then some accent, eyeliner, eye shadow, lip rouge, and of course I painted my toenails and fingernails.

I wore some low heels with open toes, to read off the toenail polish and looked at myself in the mirror. I knew I was a guy in retarding force, but I could hardly assure when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o'clock. My knees were wobbly as I walked to the door. I looked through the eyehole and for sure plenty it was lusterlessness. I opened the door and let him in.

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

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

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

"I don't think we should do that, matte. I'm not one of your piffling 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 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 delight out of this.

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

"Matt, this feels 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 wondrous, one of the sexy girls I've seen in a while."

"You've got lots of girls - real girls, not fake ace, like me."

"Don't pull yourself down. Most of those lady friend have nothing on you."

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

"Let me take you out to dinner, Lynn"

"Just let me convert into some rule dress, 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 someone sees me - recognizes me ?"

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

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

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

"I don't know."

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

"That makes me feel really weird."

"And maybe a short turned on ?"

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

"I do, and we should."

With that, matt got up and make me to my feet. He wrapped his arms around me and pulled me close. I think my eyes were the size of discus and my knee joint were getting fallible as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the doorway. When we got there, he stopped and turned.

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

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

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

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

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

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

matt actually had money, which is yet another reason why about of the missy fell all over each other to get to him. We went downstairs to his brand new drear BMW Z4 convertible and he opened the door of the car for me. I managed to sit down in a somewhat ladylike manner - I don't think I showed too very much. He got in and drove us to a very nice restaurant.

He used valet de chambre parking and walked me in, holding the threshold for me. I still felt Wyrd as shite, but just tried to ignore how I looked and enjoy myself. Matt ordered a skillful bottle of wine for us, and I really needed something to booze. I downed my first glass before he'd taken to a greater extent than a couple up sips of his wine. Matt poured me another glass, but I took it a little slower.

The server seemed very taken with me, and when he thought I didn't notification, tried looking down my blouse. Several former men seemed to notice me, which made me squirm in my seat. One guy who works with lustrelessness stopped at the table to babble out with us. I'd met him several times before, but he clearly didn't tell apart me.

"fountainhead, flatness, who is this beautiful dame with you tonight ?"

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

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

"And I'm very pleased to receive you, Lynn. mat is clearly a very prosperous man. But if you want a change of scenery, give me a call, I'd love to show you a soundly time."

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

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

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

Oliver bent down and kissed my cheek before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot chick. Half the men in this blank space would dump their date for a prospect to deal you home."

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

We had a lovely dinner and I continued to fuddle way more than I should have. This wholly scene had blown my mind so a great deal I didn't know what else to do. A few former men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to talk to mat. We finished dinner party and I thought Matt would take me back to my place.

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

"Are you sure about that ?"

"You're taking a walk of life on the untamed side, just choose a bit longer walk."

flatness wouldn't take ‘ no'for an answer and tug us to the hottest gild in townsfolk. This was the sort of place that would never let the like of me inside. They must have had a century people lined up waiting to get in. flatness 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 debauched number and I was already half plastered so I went out to dance with him. We danced respective fast dancing, then a irksome phone number came on. I thought we'd go sit down, but instead, matte pulled me shut down to him to dance.

He had one hand on my upper back, holding me slopped, as his former hand came down on my ass. He began to fondle my ass, which made me wiggle. I could palpate that flatness had a hard-on as he did that. That scared me more than a little, but I wasn't sure what I could do. I felt helpless as we danced. When the bit ended, Matt stopped, held me fast, and kissed me.

My knees got so frail that if he hadn't been holding me rigorous, I'd probably have slumped onto the floor. He gave me a foresightful kiss, and to my surprise, I began to snog 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 arcminute before he walked me back and we had another crapulence.

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

As I said, I'd been Matt's wingman to a greater extent than a few time, and had seen him this way with charwoman many times before. I also knew that in to the highest degree cases he ended up taking those women menage 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 recollective we danced and drank, but by the time matt was ready to leave, I was really plastered.

I thought lustrelessness was going to drive me back to my piazza, but instead he drove me to his apartment. As I said, Matt had money, and he had a very prissy two bedroom apartment - nice furniture and all that. piece of me hoped that he was going to let me break apart in the spare bedroom. Another theatrical role of me wanted anything but that.

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

"Lynn, honey, there's no haste. Just relax and enjoy your walk on the uncivilised side."

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

"lustrelessness, 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 make to go any farther."

"Lynn, sister, I've shown you a good clock time. I've made you sense good. You seem to be getting into this. Can't you assist me feel in effect too ?"

"What… What did you want me to do ?"

"If nothing else, can you at to the lowest degree go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

matt kissed me and stroked my ass as he unzipped his pant with his other manus. He pulled out his cock, which was already grueling and standing straight up. He kissed me again, then gently pushed my head down toward his prick. I got close and looked at it. It was longsighted and concentrated and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the head of his tool between my lips.

flatness moaned and leaned back, still keeping a mitt on my head. I let the principal of his shaft moorage from between my rim, before taking it back and going just a little farther with it. I bobbed up and down on his prick, gradually taking it deeper and mystifying into my lip. I'd never had a dick in my mouthpiece before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my mouth and flatness seemed to like it. Some precum came from the tip, and it had a salty gustation, 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 shaft as I sucked the rest of it. By now, Matt was moving his hips, almost fucking my mouth, as he held my head tight.

flatness moaned loudly and got very rigid as his prick erupted in my oral cavity. He held my head with both men as he emptied his bollock into my pharynx. I swallowed his cum and gasped for breath, though it took a brace of swallows to get it all down. It gradually eased and I cleaned his dick off as I pulled my head back from it.

lusterlessness 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 bother him. Matt continued to kiss me and I didn't even realize it as he pulled my annulus up over my ass and began to caress my ass through my step-in. He even snuck his hand 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 consonant him. Maybe I was enjoying it all too lots, and maybe I was just too drunk. Before I even realized it, lusterlessness had removed my skirt and blouse and was carrying me into his bedroom. I was so far gone at this detail I didn't know or worry, or maybe it was what I really wanted.

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

"Do it, mat. Do it."

flatness set me down on his bed on my hands and knees and pulled down my scanty. My dick, which had been ignored for so long sprang to care, but Matt was interested in other things. He took off his pants and shirt and got in bed behind me. He reached into a drawer in the table beside the bed and got a underground of lube.

Matt rubbed lubricant over his shaft, 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 second or two. He snuck a second finger in and began to feel fuck my ass, and in spitefulness of myself, I began to make love him back. Matt leaned down and kissed the back of my cervix as he pulled his finger out of my ass.

I felt the head of his cock at my asshole and tensed for just a mo before relaxing. At this peak, I think I wanted him as much as he wanted me. I felt the head get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but Matt took it easy and retard at first, until I really started to get into it.

I soon felt his hip joint 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 result me the sleep together alone. Now matt was fucking me and I was in heaven. I felt his shaft lantern slide deep in me and fill me up. It turned me on in direction I'd never have expected.

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

Matt collapsed onto me and I collapsed and we rolled onto our slope, with his shit still inside me. I was on a intimate high school and wanted goose egg more than to keep feeling his hammer in my ass. His prick was getting sonant, but I wanted to retain him in me as long as I could. As we came off our in high spirits, matt began to stroke my berm and osculate the back and slope of my neck.

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

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

"I just might admit 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 keep as much of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the side by side morning with Matt still spooning me and with his intemperately cock pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's heavy dick against my ass, I'd have leapt from bed and gotten out of the room as fast as I could. Instead, I moaned and moved my ass around against his prick.

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

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

"Lynn, child, thank you for last nighttime, and for this dawn too."

"I hope we'll have Thomas More than just close Nox and this morning."

"If that's what you want, we don't have to bar 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, Matt's putz had slipped out of my ass and I'd rolled over facing matt. I kissed mat, and he kissed me back and began stroking my eubstance. We spent a farsighted time kissing and touching each other before we got up and went to the shower together. Without my clothes, my bra, my step-in, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his dick, I got down on my genu and sucked him off again. With my makeup off and pilus 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 last Nox. I had a little war paint in my purse and could do lipstick, eyeliner and a little bag, to take a crap me more like Lynn.

The more I looked like Lynn, the to a greater extent matt seemed to be lovesome. He fucked me once more before taking me dwelling, and we made a escort for that evening.

When I got home, I looked at myself in the mirror, then just slumped onto the cast and shake up my head. I could feel matte'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 act it out along the way. For now, at to the lowest degree, I guess I was Lynn, until matt got tired of me or I got tired of it all. I guess Karen's extra wearing apparel were now Lynn's clothes till farther notice.

lustrelessness took me out again Saturday night, and took me back to his topographic point. We were not as tired or drunk and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to catch some Z's, I was starting to find conflicted. Was this really how I wanted to live out my living ? And how retentive was Matt likely to be interested in me ?

We fucked a twain more times the next daybreak and I went home. I decided that Lynn would only be on Friday and Saturday nights. I was going to exist and form as Lenny, the eternal sleep of the clip. It was hard. We all want to be appreciated. We all want someone to recall we are exceptional. Lenny is n't especial to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as matt 's wingman. Matt always found an attractive fair sex to take base. I was a little covetous - both of matte and of the woman. On rarefied social occasion, I 'd be Lynn during the week, and Matt would come to my property to jazz me. Usually Lynn was a weekend thing, but some weekends, mat had other plans.

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

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

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

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

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

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

'' Well, your guy appears to be about ready to step out with another cleaning woman. Would you have any interest in doing the same ? Or are you strictly into Guy ? ``

'' You mean ... you 're interest in char ? ``

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

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

Nicole reached up, and stroked my face. I 'd shaved as cleanly as I could before going out with lustrelessness, and my facial hair is not thick, but there was the slight vestige of very igniter stubble and I could narrate by her expression that she felt it. Nicole leaned forward and kissed me.

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

'' And you like that ? ``

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

'' I like adult female, I 'm just ... ''

Nicole took my helping 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 match of dissipated dancing, and I really enjoyed dancing with Nicole. hell, as Lenny, I had worry getting woman to even trip the light fantastic much with me.

A dim identification number came on and Nicole grabbed me and pulled me close. She put one hand in the middle of my rachis and the former one down over my ass. I giggled and squirmed as she caressed my ass through the dance. I glanced around and no one seemed to even notice us or what we were doing.

At the end of the dance, Nicole gave me a kiss that almost buckled my genu. I could experience my dick getting unvoiced and barely being restrained by my pantie. My mind was blown. We stood there kissing for I'm not even sure how long. I'd never had a char buss me like that before, and I was in no hurry for it to end.

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

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

"Well, I guess I don't mind, at to the lowest degree 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 buss. We finished our drinks, danced a bit more then Nicole invited me back to her place. Nicole was an indoors 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 involvement in the likes of me.

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

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

"I like girls, I just never had a lot luck before."

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

I felt a little uncertain. Nicole was pretty and she seemed willing. I just didn't understand why she'd have any interestingness in me - not after knowing that I was a guy dressed as a lady friend who'd been out with a guy. Look, I'd never had any char leave to give 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.

lusterlessness had left me and gone off. I could either visit an Uber or find out what Nicole had in mind. Honestly it was probably honest than what matt had done, even though I seemed to savor fucking Matt. I sat for several second, just pondering the possibilities. I looked at Nicole who sat there with a little enigmatic grinning on her face, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walking on the barbarian side anyhow, why not take the air a niggling 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 Matt's BMW, but a Nissan 370Z a duo of years old. It was certainly nicer than my eight class old Civic. Nicole opened the car door for me, which surprised me a bit. Yes, Matt had been doing the same, but Nicole was a woman and knew what I was down below.

I stood slightly puzzled for a second before smiling at her and sitting down in a ladylike mode. Before she closed the car threshold, Nicole leaned over and kissed me. She came around, sat down in the driver's tail and started the car. Before she put it in gear wheel, she smiled at me again and gave me a nimble kiss.

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

"best pass I've had in a long time."

"better than your little young man ?"

"No question."

We were stopped, getting ready to exit the parking lot. I leaned over and gave Nicole a candy kiss. She smiled and stroked my forefront, before taking us out on the road. She drove us a few naut mi to her flat. It was on the second storey and we had to walk a flight of stairs, but we had our blazonry around each other, giggling and petting each other as we went.

Nicole had a nice little one chamber berth, clearly feminine, with a muted floral sofa and chairs, along with some art mark on the paries. The prints were largely of womanhood and men, along with a few where it wasn't quite clear if it was manly or female. She walked me over and we sat on the lounge, and she put her arm around me.

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

"I really just started dressing up in my sister's apparel as a turn-on. I told lusterlessness one meter when I was drunkard and he wanted me to dress up for him."

"Obviously, you did."

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

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

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

"But you were into hombre ?"

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

"rich person you been with any other guy cable than him ?"

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

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

"I'd love that, Nicole."

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

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

"What about your little boyfriend mat ?"

"I think he's getting a piddling tired of me."

"What if he isn't ?"

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

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

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the farsighted clock time. I wanted to a greater extent of course, but I didn't want to rush matter and tump over her and maybe make her send me on my way. Nicole stroked my body, mostly back, arms, and ass, so I followed her lead and did the Lapp to her. After a long stretch of kissing and touching, Nicole stopped.

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

I was more than happy to do so, though my manpower were shaking as I began to undo the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her doll, and she asked me to draw out it loose and take it off her. She sat there with only her bra on the amphetamine half of her consistence. I hardly even noticed as she took my blouse off me.

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

My bra, of course, was filled with padding, not drop the ball, 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 pleasance through my eubstance. She had both hands on what would have been my boobs, if I had any, so I placed my early hand on her other breast.

I was a little interested about pushing it too far, but Nicole seemed to get even more sour 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 metre, 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 piece before she leaned back to allow our bras to fall off each of us.

My bra and padding fell to the floor, leaving my bare chest of drawers out there. I got my first look at Nicole's breasts - actually the number 1 chest I'd ever seen live and in person. I wanted to touch them but I was hesitant. I didn't want to run too fast and spoil things. Again Nicole put my handwriting on one of her pinhead, then began to stroke my vapid, boobless, chest.

Her bosom felt dumbfound, affectionate, diffused, and just so fantastic. I began to caress her boobs and nipples as Nicole played with my chest. After a piffling while, she stopped kissing me and guided my sass 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 thrash her bosom 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 breast seemed to enjoy in my care. After a bit, she shifted my head over to the former bosom, and I began to give it the same attention that I'd been giving its partner.

I spent a farseeing time kissing and pleasing her white meat, before Nicole clutched my pass tightly to her as she moaned and writhed on the couch. As it settled back down again, she pulled me back up and kissed me before sitting us both up. I was afraid that she was indicating that we were done and was going to send me on my way. Instead Nicole stood and pulled me to my animal foot and led me by the hand into her chamber. 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 bird slide down her trunk onto the floor. She stepped out of the chick, then kicked off her place. She now wore only panties, and I could see a decidedly wet spot in the front line of them, as Nicole unzipped my dame. My panty 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. Okay ?"

"Anything you want, Nicole."

"start, ask off my panties."

I moved down her trunk and Nicole lifted her pelvis 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 feet, letting me film them completely off her. Nicole spread her legs and for the starting time clock time I got to see a cleaning woman's pussycat. Nicole had shaved nigh of it, except for a narrow cartoon strip just above her labia. Nicole gently pulled my header to her nether neighborhood, though I had no idea what I was supposed to do.

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

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

I was still in full physical composition as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the head of my prick, which was as hard as I've ever seen it. tone, I'm no great shakes in that section, but I've got about six in, and it was in its broad gloriole as Nicole slid back up my body.

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

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

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

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

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

"I'm going to cum, Nicole."

"Do it cocker, correct 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 fellow would do to you, but I hope you enjoyed it anyhow, Lynn."

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

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

"What do you mean."

Nicole got off me, got up and walked over and opened a draftsman. 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 prick. She had me get on helping hand and knee joint, then got some lube from a nearby drawer, before lubing up the member and my ass.

Nicole eased the affair into my ass, until I was comfortable with it, then began to slowly fuck my ass with this strap-on. I wasn't sure I wanted her to do that, but at this gunpoint, I wasn't going to indicate with her. As she began fucking me, I began to get into it. For obvious reason, she was able to keep going a lot longer than matte 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 gimmick on her even through that. We kissed for a long fourth dimension before she turned me on my side and spooned me, with her strap-on pressure 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 jazz her pussycat. We showered together, playing as we washed each other. I went down on her in the shower bath and she went down on me after.

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

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

"That sounds great. I've got some errands and things to do this good afternoon, so you need to get your precious little ass place, 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 clock time with you."

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

I put my apparel 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 hold up 24 hours. While I sat there, my earpiece rang - a birdcall from Matt.

"Hey, babe. Sorry I left you stopping point 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 or you'd catch an Uber or something."

"Actually, she took me back to her situation, 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 play with."

"You're hotter than Toni."

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

"semen on, missy. 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 things I can do to you that she can't, unless she's like you."

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

"Are you fucking dumping me, grouse ?"

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

"Lynn, how long do you cerebrate 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 weeks. In the lag, you have Toni or one of the other many women who fall all over themselves to be with you."

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

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

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

"And you've gotten payment for that. And if or when Nicole dump me, if you aren't too big a bitch, you might even get more. In the interim, 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 attend like Nicole did too. The deviation was that I got more out of it with Nicole. It wasn't just me being fucked, I got a fortune 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 epicene enough to get off on what I did with matte, but why give up on women if I had any chance with them ? I was still sitting there in clothes as Lynn, when there was a rap on the door. I was puzzled, because I wasn't expecting Nicole, Matt, or anyone else for some time. I was a piffling leery of opening the door, when it was unlocked from outside.

I sat there shocked as my sister Karenic came in the apartment. She didn't spotlight me immediately, but turned to close and lock the doorway. She saw me and her mouth hung open up and she seemed icy in shoes until she began moving slowly toward me. Karen got over to me, reached out a hand and touched my face.

"Lenny ? What the ass ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my panty and bras too ?"

"I am."

"I got a giving station and was going to pluck up the balance of my clothes, but if you've been wearing them, I don't think I want them anymore."

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

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

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

"A girl ? A real young woman ? Not some in between or fake thing ?"

"Nicole is a tangible charwoman. For some grounds she gets off on being with me like this."

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

I looked at my place. I couldn't look Karenic in the font. She understood immediately.

"Fuck. You mean you did that too ?"

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

"But if she dumps you and you can't happen another woman, you'll go back to fucking bozo ?"

"Karen, please."

"Lenny, it's your life. Fuck who you want. Just don't show up at plate or my place 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 Saame clock 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 joint, and she took some commiseration on me and stroked my drumhead and tried to console me. It took a spell before I regained my composure.

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

"I hope you can realise and forgive me."

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

"You were always popular with the bozo. I could never get any of the girls to hold 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 girl you're with now ?"

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

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

"I don't know how long it'll last, but I'll do what I have to do to keep it going."

"Should I still call you Lenny ?"

"When I'm like this, I'm go by Lynn."

"Well, Lynn, I wish you well with your girl. And I'm not going to wear any of the clothes I left here, so they're all yours."

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