The Real Kasey Ch. 01

My story begins, for the most part, in the summer of 1996. I was just twenty-one years old at the time and I had managed to hook up with a beautiful older woman. It would not be much of a stretch to say she was a nymphomaniac, but she had a very high sex drive and a desire to explore and experience all sorts of kinks and fetishes.

Being young, and this being my first real sexual relationship, when Lisa and I started dating I was very enthusiastic about her open and wild sexual desires, but things really turned in a strange direction when she told me she wanted us to "switch sexes" in a sort of role play adventure where I'd be the woman and she'd be the man.

She told me she thought I had very nice legs and that they would look very sexy if I shaved them. With a great deal of prodding, and Lisa's help, I eventually managed to shave my body from the waist down. I told her there was no way we were going to shave the rest of me. She seemed okay with that, but after our first session together where I wore one of her pink teddies and she wore men's underwear, and I saw myself in the mirror with very nice smooth legs and a hairy chest, I agreed that I would go hairless with the exception of my head.

More than any of the other role play games or kinks that we tried, this one was my favorite. I got into the role of being female. Until it came to the actual sex, we more or less mastered our roles. I got into wearing miniskirts, high heels, stockings, women's blouses, padded bras and panties. I began wearing fake fingernails and painting them, along with painting my toes, wearing make-up and Lisa got me a long platinum blonde wig that I wore for our sessions.

Normally I only wore these things when we were alone. It was our little secret, even though I raised some questions with my shaved body and legs, especially given that it was shorts season. I brushed them off as part of what my friends knew as my wild sex life with Lisa.

Another of Lisa's fantasies was to have a threesome with two men. We had done just that, a couple months before I began shaving and dressing. My best friend Marco had been the lucky man who got to join us. We had mostly taken turns at either end of Lisa, avoiding contact with each other, and managing to violate Lisa in every way we could think of.

Lisa knew that I had, in turn, wanted to have a threesome with two women. We had failed to convince one of her friends to participate and other options were few and far between. One night we had Marco over for dinner. Lisa was being very flirtatious with him, which made me feel a little nervous. The one part of our threesome that had really bothered me was that Marco had a significantly bigger penis than I did, especially when fully erect, and I had become paranoid believing she preferred having him inside her over me.

The more she flirted with him, to the point of putting her hand on his leg when they talked and brushing his hair away from his face several times, the more jealous I got. I didn't want to express my feelings, although I definitely looked unhappy, and I was drinking much more than I normally would.

Then she shocked me by telling Marco, "You know, Kasey has been dressing up like a girl for me. He actually looks really hot, especially those long legs of his."

"Don't tell him that," I said angrily.

"You should change, honey," Lisa told me, stroking my arm. "Come on, it'll be fun."

I refused, got angry, and stormed off to my room. For the next couple of days we barely spoke, with me telling her I felt humiliated by what she told Marco. Still, I was getting dressed in my female clothes as often as I could, even when we weren't having sex. Lisa did nothing to stop or discourage me, always telling me things like I looked hot in one outfit and pretty in another.

Once we started talking again, Lisa sat down with me and told me she wanted to have a serious talk.

"This whole dressing thing started as a one-time fantasy, you know," she told me. "You kept it going way beyond that. This is part of who you are, part of your sexuality, and I am glad we brought it to the surface but you have to start admitting to yourself that this is who you are."

"I do admit it," I insisted.

"In private to me," she replied. "You hide this part of you from everyone else in your life. Your best friend Marco already knows, and he's cool with it, but you're afraid to be dressed in front of him. Why are you so scared? What's the big deal? You like wearing miniskirts and heels. So what? You look damn good in them."

"I feel totally weird about doing that."

"You love dressing up and looking sexy and it totally turns me on. You talked about going out like that, to that club, and wherever. You have to start somewhere. So why not by showing your closest friend?"

"Because it would be weird, like I was dressing up for him," I explained. "It would be easier to go out to that club when they have those drag queen shows. Then I won't feel, you know, so out of place."

A week and a half later, Lisa and I went out to the club. I was fully dressed, in makeup and my blonde wig. I had a satin blouse with my padded bra, a very short miniskirt, black fishnets, and five inch heels. I was extremely nervous, but with Lisa holding my hand as we walked in, I felt secure in everyone knowing I was with her.

We only stayed for an hour, had a few drinks, and then left. By the time I left I felt more comfortable, having had people approach me and talk to me and behave like nothing was wrong with the way I dressed or looked. Several men and women complimented me, saying I looked very sexy, or that I had "hot legs."

Over the next few weeks I got more comfortable opening up and talking about my dressing with Marco and with a few other friends. Saying it was part of my relationship with Lisa made it easier, and while some found it to be weird or abnormal, few made any kind of big deal about it. Marco shrugged it off, saying "Whatever floats your boat."

Lisa and I decided to go back to the club a month later. She had somehow convinced Marco to accompany us, saying it was to give me "emotional support." There was a lot more to it than that, having to do with things I would not learn about until later, but that night Marco would see me fully dressed for the first time.

My outfit was almost exactly the same, as I didn't have a variety of clothes at that point, except this time I went with my legs bare. I had been regularly going to a tanning salon and getting my legs waxed and really wanted to show them off. While I didn't give it much thought at the time, I was now far more interested in being noticed and getting compliments than I was in the role playing with Lisa that had started all of this in the first place.

I was starting to feel comfortable with myself, and as people talked to me I was less defensive. I would even attempt to flirt, albeit awkwardly, with both men and women. After about an hour I found myself standing at the bar, with drinks bought for me by men, as I tried to talk casually and flirt without opening myself up to anything. I hadn't even noticed that Marco and Lisa were no longer by my side.

Back then I was more than a little naïve, and completely failed to realize that Lisa was convincing men to come to the bar, buy me a drink, and hit on me. My ego was getting a huge boost from all the attention and all my nervousness about being dressed in public melted away.

By the time Marco and Lisa reappeared, I was quite drunk, and holding onto the bar for balance. I had to remove my heels and walk barefoot out of the club to avoid falling. They helped me out to the car and we drove home.

When we got to the apartment Lisa and I shared, she invited Marco inside. I collapsed onto the couch in a sitting position, my head spinning and feeling sick. Lisa made me a cup of coffee, handed Marco a beer, and sat down on the couch between us.

"Did you have fun?" she asked me.

"I guess," I muttered as I tried to regain my composure. Shots of tequila have never been my friends.

"I'm going to go change," Lisa said before getting up. "I'll be right back."

When she returned she was wearing the black satin teddy that I had worn the first time we role played as the opposite sexes. She showed off her curvy body in front of us, squeezing her 36C breasts and joking with me by saying "If only you had a pair of these, eh?" Then she sat down between us and said, "So, you guys want to fool around?"

Our first threesome with Marco had been planned, with a lot of discussion between Lisa and I and then between Marco and me. We had set all kinds of ground rules and even a safe word, "Llama," that any of us could say if we decided it was too much, or we were too uncomfortable, and wanted to close it down. This time there was none of that, it was completely impromptu, and I wasn't even sure it was happening until Marco began rubbing Lisa's bare thigh and leaning down to kiss her neck.

"This is almost like a threesome with two women," Lisa said, half-kiddingly. "You need to try to please me like a woman would, like you do when we're role playing," she told me. "Think of this as just a continuation of the role playing."

What I didn't realize was that ever since our first threesome, Lisa and Marco had been carrying on without me on the side. With Lisa's sex drive, she had no trouble coming back from a session with Marco and having sex with me, so I never caught on.

"Let's try this," Lisa said and slid down off the couch. She got on all fours in front of the couch, positioning herself between Marco's legs, and told him to take off his pants. She told me to lie on my back with my head between her legs.

I did as she said, losing my balance before I got to the floor, and then wrapped my hands around her thighs to pull myself up so I was face to face with her pussy.

I could hear, but could not see, Lisa starting to give Marco head. I was looking straight up at her vagina, running my tongue back and forth over it, and all but forgetting how I was dressed.

We continued like that for a few minutes before Lisa got up and said "Let's try this," and got up on the couch. She had me lie down under her as she sat on my face, nearly smothering me, and continued sucking Marco's cock while he stood alongside the couch.

Several long minutes later, she got up again, reversing direction so that her ass was in my face and bent down into what would normally be our usual sixty-nine position. I excitedly licked her pussy, sliding my tongue inside her, as I looked forward to her sucking my cock. Marco was moving the end table beside the couch and taking position there, just over the arm of the sofa.

Lisa pushed back against me, and had me bring my head up so it rested on top of the sofa arm with her pussy in my face. I was held firmly in place with her thighs on either side of me, unable to move my arms.

She didn't start suck my cock, or even playing with it. Instead she was kissing and licking my thighs, telling me "Such sexy legs, like a girl's, just like a girl's," which elicited a moan from me and distracted me from my oral assault on her pussy.

Lisa leaned down, raising up her ass so that her pussy was just out of reach. I saw Marco coming in close, holding his thick, ten inch cock in his hand, and guiding it towards her pussy. With my head spinning from too much drink, my body writhing as a result of Lisa kissing and licking my legs, and being unable to move, the only option at that point was to just look up and watch Marco penetrate her.

It was only after he had fully penetrated her that I realized how close I was to the action. Once Marco's cock was completely inside her and she relaxed from holding her ass up for him, his balls landed on my forehead. I wanted to say something, to say I needed to move, to say something, but I was too stunned by the fact that I was inches away from Marco thrusting into Lisa and his balls were continuously brushing back and forth across my forehead.

In between fairly loud moans, Lisa called out to me. "Kasey, reach up with your tongue, lick my clit, baby. Lick my clit while he fucks me."

I had to do some wriggling, which more or less took Marco's balls off my forehead. I had my head bent nearly backwards in order to get the right angle to reach Lisa's clit with my tongue. Even then I could barely reach it and merely teased it with the tip of my tongue.

In my drunken state I hadn't even contemplated the compromising position I was in. My only concern had been getting Marco's balls off my forehead. In tilting my head backwards the way I did, in order to lick Lisa's clit, my mouth was hanging, open wide, directly under Lisa's pussy and directly in front of Marco's cock.

Several minutes of this, and the uncomfortable position, and my tongue lost Lisa's clit. I tried to readjust myself and as I did I could see it happening, like it was in slow motion. As I struggled to free my head from being trapped between Lisa's strong thighs, Marco's cock slipped out of her vagina. It hovered there for a moment before Marco took it in his hand. I expected him to guide it back into Lisa, but instead he pointed it downwards. Before I could close my mouth, the head of his cock and at least two inches more had pushed into my mouth.

I was mortified. I completely froze upon the realization that Marco's cock was in my mouth. It hadn't been an accident. That I might have recovered from, but Marco had pulled out of Lisa and purposely guided it into my mouth while I was in no position to resist.

I started to buck, to try to throw Lisa off me and get free. I tried to pull my head down and away from Marco's cock, but then his hands took hold of either side of my head and held it down against the soft sofa arm. My head was tilted back so far that it was basically completely upside down. Lisa had partially dismounted, but was now straddling me on the couch, her vagina rubbing against my cock through my skirt and panties, as she held my arms tightly, crossing them in front of me and gripping my wrists. Lisa was beautiful, but she was a workout guru and as a result was very strong.

"Oh, he's enjoying it," Lisa told Marco with a laugh as she rubbed her pussy back and forth over my cock. "He's fucking hard as a rock. I don't think I've ever felt him this hard before."

Marco slid his cock back and forth in my mouth; never forcing the whole ten inches in, but the thickness of it completely filled my mouth and stretched my jaw. He moved it slowly; being very gentle, and making sure I didn't choke or gag. It didn't take long for me to stop struggling, and soon after I stopped struggling, my initial repulsion worse off. For a while I just accepted what was happening and just wanted it to be over, but then something changed.

I started to like it. There was no sudden switch that went off. I went gradually from repulsion to acceptance to enjoying it. When Marco pulled out, to adjust his position and balance, I moaned and gasped out the words "No... don't stop."

Nothing was holding me in place at that point. Lisa had dismounted while Marco's cock was in my mouth, and had been kneeling alongside me and watching. When she heard my moan and what I had said, barely audibly, she was delighted.

"Oh damn, this is so good," she said. "Sit up, sexy girl," she told me.

Marco had stepped back and let go of my head. I was dizzy, my head still spinning, but now from the combination of being drunk and having my head held upside down for so long. I needed to catch my breath, to get my bearings, as I struggled to a sitting position and avoided making eye contact with Marco.

"Oh honey, you are such a sexy girl," Lisa told me. My wig had fallen off, my makeup was a mess, but as she kept telling me how sexy I was, the more I felt like I really was a sexy girl in this threesome.

I kept avoiding eye contact with Marco or looking at him at all. As I sat there with him standing off to the side, whispering back and forth with Lisa, I started feeling nauseous. At one point I jumped up and made my way to the bathroom, holding onto the wall as I went, because I thought I was going to throw up. I didn't though, but when I turned and looked at myself in the full length mirror on our bathroom wall, I found myself smiling. Even though I'd taken off my heels, my legs looked good in my miniskirt. I stood and posed in different sexy positions in front of the mirror and smiled. Lisa was right. Maybe it was the tequila talking, but I was a sexy girl.

When I got back to the living room, Marco was sitting on the couch, completely naked. Lisa was on her knees between his legs. When I arrived she was just stroking his cock, and she looked up at me and smiled.

"Do you want to finish him off or should I?" she asked.

I stuttered out some preposterous response that wasn't any kind of affirmation of either option. I stared at Lisa, who got up, took my hand, and got me to kneel down alongside her between Marco's legs, now spread wide.

"Don't be nervous, we're all friends here," Lisa told me as she looked me in the eyes while taking Marco's hard cock in her hand. "Remember the first time we had that threesome together? Remember how you kept staring at Marco's cock the whole time?"

"I didn't stare at it," I insisted. "I was jealous."

"Jealous that I was getting his cock and you weren't?"

"No, I was jealous because I thought you liked him fucking you more than me."

"Look at it," Lisa said, motioning with her head until I looked at his cock while she kept slowly stroking it. "You have been fantasizing about sucking this cock since the first time you watched me do it."

"No... I mean, that wasn't why I was jealous... I mean..."

"Look closer," Lisa said before putting her hand behind my neck and gently guiding me down towards it. "Look at how big and hard it is."

"Yes... it... is..."

My heart was pounding because I wanted Marco's cock so badly I could already taste it in my mouth. If I hadn't been so inebriated, my need to resist, on the grounds that this was my best friend and I couldn't get my head around the idea of sucking cock.

I was now six inches away from Marco's thick, ten inch cock, just staring at it and panting. Lisa was running her hand back and forth across my back, in a soothing motion, as she knelt there alongside me, whispering.

"You want it so much, don't you?" she said in a whisper just loud enough for Marco to hear.

"Y-yes," I stammered, my lips quivering.

"Say you want it. Go ahead, say it and admit it to yourself."

When I paused and said nothing, Lisa gently pulled me closer towards Marco's cock, continued lightly rubbing my back, and stroked Marco's cock slowly while pointing the head of it directly towards my mouth.

I leaned down in one quick motion, overcome with desire, and took the full head of Marco's cock into my mouth. Lisa was right. Ever since that threesome, when I first saw Marco's cock fully erect and going into Lisa's mouth, I had been fantasizing about sucking it. There had been little else I'd thought about, even as I tried to deny it, I just couldn't put the thought out of my mind.

All that desire was released in that moment as I willingly took his cock in my mouth and sucked up and down hungrily. As much as I wanted to, I couldn't take the whole thing, barely half of it, but I worked it up and down and swirled my tongue around the head like I'd seen Lisa do.

Hearing Marco moan and gasp as I sucked him put me off for a moment. He had been my best friend for many years, since we'd been in grammar school, but I kept going. As wrong as it felt, the longer I went on sucking his cock, the more it began to feel natural. Marco had always been the dominant one in our friendship, deciding where we would go and what we would do. I always followed his lead. When he wanted to skip school, I jumped on board. When he started dating a girl, I'd end up dating her friend.