This needs a little explaining. Several years ago I met Bob at a Super Bowl party held at a local bar. A friend of mine who also dresses on occasion introduced us. Bob was very shy so in our short conversation I gave him my card. I was hoping he would call some time.
A week later he did. We meet at the same bar after work for just a few beers. Nothing happened. We just talked sports. Before he departed I asked him if he would like to meet again. He said yes and we became friends. We would meet several times a week but only for a few beers. I could see I was going to have to take the lead so I asked him if he would like to come over to my place on Friday afternoon. He agreed and sure enough that Friday he showed up with the beer.
I still wasn't feeling safe telling him about my dressing, although I thought my cross dressing friend had probobly told him about me. So it was an all "male-male just friends" relationship. We shared the latest jokes we had heard. Talked sports and cars. I could tell he was very nervous and figured this wasn't going any where.
So, what the hell. I said; "You seem so nervous, is there something wrong?"
He said he had something to confess to me and didn't know if I would like it. I encouraged him to talk and he finally told me he was gay. I wanted him to feel at ease after telling me something that was obviously so hard for him. So I said; "Is that all? Come with me."
I lead him back to my bedroom where I threw open my closet door and said; "See all those dresses."
Then I pulled open my panty drawer and said; "See all those panties, well, they're all mine. I'm a cross dresser. I love being a woman. Now, we both have shared our little secrets and it's no big deal."
We went back to the living room and he seemed to calm down a great deal. I knew he was curious about my dressing so I opened the conversation back up by asking if he ever dressed. He said no. I told him he should try it some time and if wanted to I would let him wear some of my close. Maybe help him out with it. He declined but asked me a lot of the same usual questions that I've been asked before.
Then he asked if I was gay also. I told him that as a woman it was only natural for me to want to please a man. At that point I turned the conversation back to him and asked how long he had been gay and what sort of stuff he was into.
He finally took a deep breath and said he was a small man. I didn't understand at first but he went on to say his cock was small for a man his size and he had always been ashamed of it. Although he liked woman he was embarrassed about his cock and it had kept him from being with many woman.
He had found men didn't mind as much. After a long time of just receiving BJ's from men he tried giving as well as receiving and found he liked it. In fact he enjoyed it very much.
I got up to get us another beer and when I returned I sat down next to him on the couch. Kind of facing him. He took his beer and I sat mine on the coffee table. I reached over and as I placed my hand on his leg and I asked; "May I?"
He didn't say anything so I continued. As I moved my hand to his crouch I said; "Size doesn't matter to me at all."
He still didn't say anything but was watching my hand. I knew his cock had to be hard but really couldn't feel it through his pants so I unbuckled his belt, unbuttoned his pants and pulled his zipper down. I reached my hand in and sure enough found a small hard dick.
As I fondled his cock he reached for mine and was having trouble getting my pants open. I stood up and removed my pants revealing that I was wearing panties and bra. I finished undressing in front of him leaving my panties and bra until last.
Once naked I reached out and took his hand pulling him to his feet. As I removed his pants he removed his shirt. Seeing how I was already on my knees in front of him I took his little cock into my mouth and started giving him a good blow job.
Before he climaxed I stopped and told him to lay down on the couch so he would be more comfortable. Once there I completed my BJ to his small but perfect in every other way cock. Once finished I let him lay there and while he finished his beer I lightly fondled his balls and cock.
For some crazy reason I've always loved playing with a soft cock. I told him how much I enjoyed doing that and we just enjoyed the moment. As he started to get hard again he said he'd like to "do me." To my wonderful, wonderful surprise I found he really did enjoy sucking dick. He really got me off good.
After that nothing else really took place. We finished the evening off watching a ball game on TV and he went home around midnight. However, he called me the next day and asked if I wanted to do something that night. I said sure and left it at that.
I really didn't want to go out with him. I wanted him all to myself for a real good time. When he arrived I was fully dressed. A short full skirted black cocktail dress. Black thigh high stockings. Black panties and bra. Matching heels. My best wig. I had spent almost an hour on my make up.
When he arrived I sung the door open wide revealing myself in one swoop. I spun around letting my skirt swing out and said; "Well, what do you think?"
His eye's beamed with delight and with a big smile he said I looked great. When he came through the door I reached over and gave him a lite kiss on the cheek and said Thank You. He blushed when I kissed him and again when I reach up to rub the lip stick mark off his cheek.
We spent a wonderful evening and he treated me just like I was a real woman. But finally when I realized he wasn't about to make the first move I asked if there was something wrong?
He finally, after some couching, said that he had always had trouble making advances toward woman. I told him not to be silly that we had already been together and that I would enjoy any and all attention from him. This broke the ice and he came to me. He took me in his arms and gave me a real good kiss.
What could a girl do? I led him to the bedroom where I undressed him. But before I could do anything else he started removing my dress from me. Once it was off he stopped leaving me in my panties, bra and stockings. He said that was the way he wanted me. He laid me down on the bed moved over top of me.
I love it when a man lays on me. I could feel his little cock all hard and pressed against my belly. He started kissing me and then slowly moved down where he pushed my bra aside and sucked my nipples. That drives me wild. Then he continued to moved down to my cock. Pulling it out where he could suck me until I couldn't stand it any longer. I exploded into his mouth.
Once I had finished he sat up. I figured it was my turn to give him the best I could. Instead he started removing my panties. I lifted my butt and legs so he could. Then he moved over on top of me again and gave me a kiss.
Without saying a word he reached down and pulled my legs up. Hooking them in his arms. In this position I could feel his cock pushing at my ass. I knew then what was coming and just smiled at him.
I wanted it and so did he. He continued to push and I relaxed as much as I could. Finally I felt the head slide into me. I was surprised that it didn't hurt like it had when other men had entered me. He continued slowly to push into me and drawl back then push again. I couldn't help but return the pushes. Finally I felt his balls against me and I knew he was as deep as he could go.
He stopped long enough for me to get use to it. I smiled at him and said it felt wonderful. He leaned down and kissed me. At that point I almost climaxed again.
I had done this with other men before. It had always been painful at first. I had always felt it was to much pain for the pleasure. But this was different. There wasn't any pain. It was all just pure pleasure. Slowly he started to move in and out of me. With each stroke into me I would push back to get all he could give. It was driving me wild.
As he started to speed up I wrapped my arms around him and said; "YES, give it to me. Harder, faster."
And he did. In just a few moments he was ramming into me as hard and fast as he could. I couldn't keep in rhythm and so I just laid there letting him have me to his satisfaction..... and mine. I felt his small cock as it started to get harder and larger inside of me and then the hard pulses as he shot off in me. I couldn't stand it any longer. I exploded in a wonderful orgasm. Shooting my load all over his belly above me.
Once he had finished I told him; "Please don't pull out of me. I love it so much. It's wonderful. Your wonderful."
But it started to go soft and slid out to my disappointment. He rolled off me and we just laid there catching our breath a moment. Then I got up and went to the bathroom where I cleaned myself. I carried a wet wash cloth and towel back where I cleaned Bob up.
After I had finished he pulled me down to him and gave me a wonderful kiss. We must have laid there an hour or so kissing, hugging and feeling each other. He said he loved feeling my stocking covered legs and I loved him feeling them. It felt so wonderful as he sucked my nipples.
I got so hot I couldn't stand it any longer. This time he laid on his back and I sat on top of him. Again his small cock slid into me with out pain and it felt so good inside of me. I rode him slow and long until we were both just about to climax. We stopped and I moved on to my knees. As I hugged a pillow he entered me from behind. He really got into it and pumped me hard. His belly slapping against my butt. I had never had it like this before and it felt wonderful.
Then it began. I started feeling it some where deep inside of me and it just kept coming. With each thrust it built more and more. Finally it reached it's peek and I was wild with pleasure. Such an orgasm I had never experienced. Then instead of going away it just started to decline in the same slow way it had come on. Just about then Bob started to reach his climax and I felt him once again explode into me. With that we were finished for the night. Although he did spend the night and we again made wonderful love in the morning.
We became an item after that. Spending as much time together as possible. I was his woman. He was my man. It was a wonderful time in my life. But sadly it had to come to an end. His aging parents needed his attention and I couldn't leave my career.
He moved to the east coast and long distance romance is hard to maintain. We drifted apart over the next two years.
Last week, totally to my surprise, the phone rang. It was Bob. All I got to say was Hello before he, in one long sentence said: "I'm coming to see you, I'll be there on Friday, meet me at the airport, It's been to long, I've got to see you, I've missed you so much I can't stand it."
Then there was a pause as I took in all he had just said. Before I could answer he asked; "Is it OK?"
I answered, "Oh Bob, Yes it's OK. I'll welcome you with open arms. I've missed you to. Please come as fast as you can."
So here I am killing time waiting until it's time to leave and meet him at the airport. To hell with the world. Although I don't pass in public very well I'm wearing a new summer dress. All new lingerie. New everything. I'm all ready for my man to come home.
"It's time to go, Bye-bye. Susan