To begin with, this occurred during a sleepover with someone close to me. We often baby sat for his parents. We did everything together and were rarely apart. So when he would get stuck with the baby, we would just spend the night at his parents. The evening proceeded as usual. We played with his infant sister and watched a few movies. We cooked popcorn and had eaten dinner earlier.
Finally, his sister went to bed and the house became quiet. We lay on the couch watching another movie. I guess I fell asleep in the middle of it.
I awoke, slowly, with this pleasurable feeling. I was rock hard and I was starting to breath hard. I realized, someone was fondling my dick and balls. It felt really great and whoever it was, knew how to handle things. The hand was slowly and gently stroking my cock and alternately juggling my balls. I could tell, they were trying not to wake me. They were caressing everything very gently.
I lay there pretending to be asleep. It was dark, the television was off and only a dim light from the kitchen was on. I could not make out exactly what was happening to me. I wanted to find out, but it felt so good, I did not want them to stop.
I was lying on my side and they were behind me. They seemed to be having difficulty grasping everything. I decided, while still pretending to be asleep, to turn over on my back. I let out a low moan and slowly rolled over. They jerked their hands away quickly. I just lay their still pretending sleep. Nothing happened for several minutes. I think they were watching to see if I was still asleep.
Finally, I felt the hand reach under my underwear again, very slowly, and grasp my cock again. I could tell they were straining at the rim of my underwear. The hand slid out and I felt the fingers slowly pulling at the top of my underwear. My underwear started sliding down. Very expertly, I felt them totally removed in a flash. I did not move. I guess they were waiting again to see if I would wake up. For several minutes, nothing.
Now the person was kneeling beside the couch and began fondling me again. I could feel their breath on me and I could tell, they were very aroused. This excited me even more. I was now rock hard and I could feel pre-cum oozing out of my cock.
They tried for awhile to be gentle, but, I could tell, while they were jerking me off, they were also pleasing themselves. As they approached climax, the fondling was no longer gentle and they spoke, saying, "I know you are awake, please let me finish, I will make sure you cum, I promise!"
I recognized the voice, it was my friend. I thought a minute and finally said, "go for it, there is no turning back now!"
With this, he slid his hand down and cupped my balls, took my cock in his mouth and started sucking me off. I was in heaven! He gave great head, the best I had up to that point! His mouth felt so warm and good. I began hunching out of control at his mouth. He rode my cock like a pro.
After just a few minutes of this, I came! I spewed out in waves! He held on, apparently gulping every drop down. I finally stopped cumming and collapsed back. He held my cock in his mouth and a few seconds later, he started cuming, screaming, "I am cuming!!"
I was spent. Even though I was a little confused, I just lay there, unable to speak. I felt him stand up and I could hear him walk across the living room towards the kitchen.
He turned on the kitchen light. There he stood, all dressed up in female attire. He was gorgeous!! He was wearing a black bra, black garter, black panties, black high heels, and black hose. He had on a blond wig and what looked like perfect makeup.
He just stood there, posing very seductively. His cock and balls were sticking out of the front of his panties and you could see the remnants of sperm all over the front of him. He wiped it off with a dish towel.
He had been staring at me the whole time. I could tell he was expecting some sort of response, but I simply did not know what to say. Before this, we were just coworkers and close friends. Now what?
Finally, he reentered the living room and stood a few feet away from me. He said, "Well, do you like, or not?" He motioned his hands up and down, indicating his attire. He had repacked his gear and he was really attractive. He had a great ass and legs. I could see, he was totally smooth shaven. As I looked, I realized, I was hard again.
I did not know what to say, so I just motioned with my hands at my hard cock.
He smiled, got down on his knees and grabbed my cock. He took his panties off and again exposed his now hard cock. We stood up and started kissing. Our cocks were rubbing against each other and it felt great. He had on perfume and he smelled wonderful. He began slipping his tongue in and out of my mouth.
We were really going at it. We rolled down onto the floor and wrapped our legs around each other. We worked our mouths up and down each other, finally ending up in a sixty nine position. This was totally new to me. But, as I tried it, it felt really good having a cock in my mouth. I kind of felt, in control. His cock told me of the pleasure I was giving him.
After a few minutes of 69ing each other. He stopped, saying, "Not yet, will you fuck me, please? I have wanted it from you for so long." While telling me this, he had rolled over onto all fours. He was putting some sort of lotion on his rectum and motioned me over behind him.
I positioned myself between his legs and mounted him. I placed my cock against his anus and slowly pushed. With the lubricant, I slid right in. He gasped as if in pain. I started to withdraw, but he stopped me, holding my ass with one of his hands. He said, "No, don't stop, it is okay."
I slowly started stroking in and out. God he was tight and so very warm. He began moaning and hunching back at me. I started fucking harder and harder. I could not control myself any longer and I fucked the shit out of him. He was screaming with pleasure as I climaxed, rammed completely inside of him. What a climax that was!
I rolled over on my back, fully spent and totally exhausted. I watched him still there on all fours. I could see my cum pouring out of his ass as he was still jerking himself off.
I do not know why, but a sudden urge came over me. I leaned over and pulled myself underneath him. I pushed his hand away and took his cock in my mouth. I barely got it in my mouth and he started cumming. I did not know how, so most of it ran out of my mouth. It actually tasted strangely, good.
That was the first time, there were many more afterwards. I finally knew, I was bisexual. We had an affair that lasted for several years.
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