Company Pier

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First date for Lisa and Bill, a little awkward.
1.8k words
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kokshur
kokshur
25 Followers

My name is Lisa. Bill and I have been working together at the same restaurant for almost a year now. We've had a friendly, easy, somewhat flirtatious relationship almost from the beginning. But I never expected anything truly personal to develop. For one thing, there's an age difference. I'm about 15 years older than his age 21. Of course, being a lady, if asked my age, I naturally shave a few years off, so he may think that the difference in our ages is more like 10.

Then, too, I've got a sort of rule about not fishing off the company pier. Not to mention I never found him physically attractive. Oh, he's cute, in a geek chic kind of way. And he's tall. About 6ft one. But he's skinny. Not thin, skinny. I generally like my men on the muscular side.

Don't get me wrong, Bill is kind, sweet, funny, and smart. But even with all our casual flirting, the idea of dating him or anything like that just hadn't occurred to me. So it took me completely by surprise one day when, as we were both getting off work at the same time, he asked me if I wanted to go get a drink or something. He said it in such a way that I guessed it had taken him quite a bit to work up the nerve.

I was further surprised when I heard myself saying, "I'm really not in the mood to go to a bar or restaurant. Would you like to come to my place for that drink?"

And I was also surprised at how happy it made me that he agreed.

You have an idea now of what Bill looks like. You are probably wondering about me. I'm about 5ft six in my bare feet. Which I almost never am. I generally wear shoes with at least 3 inch heels. I'm blonde with deep brown eyes, naturally thick eyelashes, a longish upturned nose, and full lips. As for my figure, it is often admired. My breasts are the size of softballs. I have a narrow waist, a pretty (so I am told) derriere, and long legs. That night I was dressed all in black. I had on a sleeveless, collarless, linen blouse that showed off both my cleavage and my midriff. I was wearing a wraparound knee length skirt, my panties were black to match the rest of my outfit, thigh high fishnet stockings, and my shoes were open toed and four inch heels. I was wearing no bra.

We got to my place and I put some soft jazz on the stereo and made us each a vodka martini and we sat near each other on my sofa. We sat and sipped on our martinis. Listened to the music and made small talk for a awhile. Then Bill said, "My feet are aching. Would you mind if I took my shoes off?"

I stood up. "Take off your shoes and your socks and I'll give you a foot massage if you like. I'll be right back." I said. I came back a minute later with a small bottle of baby oil. I like baby oil for massaging. It's smooth, gentle, and I like the scent.

I sat back on the sofa, put a small brown pillow on my lap, patted the pillow and said, "Put your feet on up here." I poured a little oil into my hands and began working it into his feet.

"Oh, that feels good," he said, "Soo good."

I continued massaging one foot and then the next. Every once in awhile he'd moan with pleasure. As I leaned into my work my breasts would occasionally brush against his foot. I hoped he was as aware of that as I was. On an impulse I placed a few kisses on his toes.

Suddenly he pulled his feet away, and for a moment I was afraid he was upset. Instead he said, "Enough kisses for my feet. I want some kisses for my lips." He scooted over, put an arm around my waist, put his other hand on my chin, tilted my face up, and kissed me.

That first kiss was gentle, even tentative. The second kiss was anything but. He crushed my lips with his. His tongue forced its way into my mouth. I returned his kisses with enthusiasm. The hand on my chin worked it's way down my neck, past my collar bone, over the fabric of my blouse. He rubbed and squeezed and fondled my boob through the thin fabric. God, I was getting hot.

I felt him unbuttoning the top button on my blouse. I knew I had to stop this. NOW. Somehow I pulled myself away. My hands on his shoulders, I pushed myself away. "Please," I said, "there's something you need to know before things get out of hand.

"I don't get it," he said, "I thought you were as into this as I was."

"I was Bill, I am. But I need you to know something about me first."

"Okay, if you need to tell me, tell me." He was almost pouting, the poor dear.

I stood up and took a couple of steps, turned and faced him. As I spoke I unfastened my skirt and let it fall to the floor. "There's no easy way to tell you this. I guess I'd just better show you" and I pulled my panties down so that my cock could be seen. It had started to get erect as we had been making out but my nervousness at what Bill's reaction might be had reversed that effect. It's not a big cock. It gets up to maybe 4 and a half inches fully erect and in the circumstances there was considerably less than that hanging between my legs at that moment. But it is a cock and Bill quickly realized it.

"JESUS FUCKING CHRIST" he exploded. "YOU'RE A GODDAM MAN??" he yelled.

I started to cry. My lower lip trembled as I said, "No. I'm not a man. I'm a woman. I am. I'm not a man. I'm a woman. A woman with a penis, but I'm a woman." By now the tears were rolling unstopped down my cheeks.

"Oh jeez," he said, "Don't cry. I'm sorry I yelled. You took me by surprise. I'm sorry. Please stop crying." He stood up, took a handkerchief out of his pocket and handed it to me saying, "It's clean, wipe your tears." Then he pulled my panties back into place took me by the shoulders and sat me back on the couch, sitting back down himself. "You took me by surprise." he said again.

I couldn't stop crying. "I'm sorry," I said, "I probably should have told you sooner but I, I didn't know how and then, then you were kissing me and I didn't expect that and, and, and, if you walk out right now and pretend none of this ever happened I'll understand."

And I was still sobbing like an idiot. Bill had seen where I keep tissues on the end table. He tugged the tear soaked hankie from my hands and handed me some tissues. "Blow your nose." he said gently. I did. He took those tissues from me and handed me a couple more. "Now wipe your tears." and then he put his arm around my shoulders and pulled me close to him and held me gently. After I really had stopped crying we sat there silently for several minutes. And for those minutes I was at peace.

But eventually one of us had to say or do something. It was Bill. He said, "I wish I could tell you that I'm totally okay with all this, but the truth is I .just don't know how to react. I need some time to deal with it. I need to go now. I'm sorry. I'll talk to you soon." Then he put on his shoes and socks, picked up his coat and was out the door.

I sat for a while after he had left. Then I got up, turned off the stereo. Went to my bedroom. Got undressed. Took off my make up. I opened a drawer where I keep panties I don't wear anymore. Selected a pair of red silk ones. I laid down on my bed and positioned myself so I could see myself in my dresser mirror. With the panties in my right hand I started rubbing them all over my body. With my left hand I started playing with my tits. Soon I started to get an erection. I wrapped the panties around my penis. I rubbed, squeezed, and stroked it.

I thought about Bill. I remembered the kisses we had shared. I remembered the feel of his left hand around my waist. How good it felt when he held me close. I remembered the fingers of his right hand on my face, and then my neck and then down to my tits. I remembered my nipples stiffening as he pressed against them. My cock responded too. As I remembered I was still playing with my tits. Still squeezing, rubbing, stroking my panty wrapped cock. And I realized that for the first time since I'd known him I was masturbating with Bill as the center of my mental fantasy.

Next I remembered feeling Bill unbutton the top button on my blouse. Now I let the fantasy go further than the reality. After the first button he unfastened the next and then the next. I imagined him pulling back to admire my breasts. Holding one in each hand and telling me how beautiful they are. Then leaning in and taking first one nipple and then the next into his mouth.

Now I imagined leading Bill into my bedroom and undressing him. Kneeling, topless, and taking his erect cock into my mouth. In my fantasy I gave him the best blow job of his life. I imagined him taking his cock out of my mouth a moment before orgasm and cumming all over my chest. Then in my fantasy I stood to face him. He pulled me close to him and kissed me. Then he took off my skirt and tossed it away. He pulled down my panties. In my fantasy he was delighted to discover my penis. He picked me up and laid me on my bed. He kissed the head of my penis. Then he licked it. His tongue explored my whole penis and my balls. Then he slid my penis into his mouth and started to suck on it. And all the time I was fantasizing I was masturbating. And when I came into the red silk panties in my fantasy I was cumming in Bills mouth.

After I cleaned up I turned out the lights, crawled between the sheets and cried myself to sleep, scared that my fantasies might never find fulfillment in reality.

kokshur
kokshur
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fregenfregenalmost 19 years ago
Poignant and sad

Well written. Distills rather nicely the problems and heartbreak of someone trapped in the wrong body. The loneliness and isolation. The plaintive affirmation of womanhood was particularly searing.

Thank you for the story.

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