Transsexual Sex with Vinnie and Jam

Gayle and I were relaxing naked on her bed. She was having a drink and smoking a cigarette while I was just enjoying the buzz that I had from having consumed nearly two full glasses of Jack after having had anal sex for the first time.

The next thing that I know, the doorbell rang and Gayle scurried off the bed putting on her nightgown. In walks Vinnie with this good looking broad. Normally, I would have been embarrassed that I was naked in front of a woman, especially a good looking woman such as this, who I have never met before, but I was drunk.

"I'm not too late, am I?"

"I've already popped his cherry, Vinnie," said Gayle. "But you can have a turn with me, if you'd like," she said bending over, lifting up her nightgown, and wiggling her naked ass at Vinnie.

"No, thank you, Gayle, I'm good. Actually, I was hoping me and my friend can party here. My wife is having a Tupperware party at the house and my girlfriend is out with her husband."

"Yeah, sure, four makes for a better party than just the two of us. Besides, Freddie looks like he's about ready for a nap." With that, she whipped off her nightgown and jumped in bed beside me.

Upon closer inspection, the woman who Vinnied accompanied intrigued me.

"Psst, Vinnie, come here."

"What is it, Freddie," said Vinnie leaning down over me.

Meanwhile, I kept staring up at Vinnie's friend. I could have sworn she had an Adam's apple. There, she does have an Adam's apple.

"Did you know that your woman friend is a guy?"

"Yeah, I know," he said turning to look at James, smiling, and waving at him. "That's my friend, James, my cellmate from prison who I told you about." He nudged me with an elbow in the ribs. "We were close, you know, tight, if you know what I mean." He inserted his index finger in the hole he made with his thumb and index finger on his other hand.

"Oh, gees, Vinnie, that's another image that I could have done without."

"Say hello to my friend, James."

I covered my nakedness with a pillow.

"Hi, James," I said with an exaggerated wave, "how you doin'?"

"I'm doing well," said James. Gees, he had the voice down pat. He sounded just like a woman.

"I'm Freddie," I said sticking out my hand.

"Nice to meet you Freddie. Vinnie has told me a lot about you."

"So, why were you in prison?"

"Manslaughter. It was self-defense really. I was with a man who was very nice until he discovered that I was a he and not a she. He started beating me, so I shot him with my derringer."

"Do you still have the gun?"

"No, the police confiscated it.

"You're drunk, Freddie," said Vinnie laughing.

"Yeah, I had to get drunk to fuck Gayle up the ass. So, what are you doin' here?"

"I was hoping to see you in action, buddy on your first time having anal sex. No matter it's not all for nothing, James gets off having someone watch." Vinnie leaned down and whispered. "He still feels like he's in prison. We had no privacy in our cell."

"So, what are you going to fuck him up the ass, Vinnie?"

"Yeah, you know, for old time's sake. I'll probably have him blow me first. He's going back in the joint for a parole violation and I thought I'd give him a bang before he left."

"That's big of you, Vinnie." I had trouble trying to compose my thoughts. "You're not going to blow him are you?"

"Nah, I told you already. I'm not gay." Vinnie looked down at me. "Gees, Freddie, you really are shitfaced, aren't you?"

"Jack and I had a good time," I said slurring my words while drinking the last of my drink. "Let me know when you two are done. You can give me a ride home. In the meantime, I'm just going to close my eyes and take a nap.

Meanwhile, James was already topless.

"You have tits! Jesus Christ. I'm so sorry, Miss. Fuck. I thought you were a man," I said apologizing all over the place. Vinnie said you were James."

"I am a man," said James as he pulled down his pants and exposed his erection. "I am James."

"Holy shit. He's got a bigger cock than me," I said looking to Vinnie and back to him. "You're one of those, one of those..."

"Transsexuals."

"No, that's not it. You're a hermaphrodite."

"Freddie, you really are drunk. James is a pre-op transsexual."

"Can I feel your tits, James?" James walked closer to me and allowed me to feel his tits.

"Go ahead, you can suck my nipples."

"Nah, that's okay. Thanks anyway. That's kind of creepy." I closed my eyes to the sounds of Vinnie having sex with his transsexual friend.