NAKED SUPPORT GROUP II
Having finally been convinced I am gay and being chronically horny I kept thinking of other sex I should explore. Particularly what it would feel like to be cornholed. I kept coming back to thinking Tim, the kid who initiated me into the world of gay sex, would be the logical one to do the job with his little weenie. When we parted we exchanged phone numbers and I gave him a call. It was a rainy Saturday noon and he was free by three. I spied an empty wine bottle ready to throw out and it was the typical shape: gradually widening from the opening to reach full circumference halfway down the bottle. Looking at it, I wondered how much I could get up my pooper before it hurt. I got some Vaseline, greased it up and tentatively worked it in. The blunt bottle opening not easy and I really had to concentrate on relaxing my hole but once in I could get it in far enough to reassure myself that Tim would be no problem.
Three on the dot I knocked on the door and he opened it naked. He wasn't hard and his weenie was really weenie. By the time I got undressed he was erect. He was a cute kid, especially with a wide smile. "So what do you want to do today," Tim asked. When I told him he looked very pleased. "This'll be a first for me," he said, and went to his desk drawer for a rubber. I had wondered how he was going to keep a condom on that little dick but he had ordered a pack of junior size rubbers from a mail order porn site. He even had a tube of lube. I got on my back, pulled my knees up and he proceeded to enter me. It went in a damn sight easier than the wine bottle and matter of fact it felt good. He was an energetic little fucker and when I felt his organ pulse in my rectum it was somehow pretty exciting. He stayed in for a minute and then his softening dickie popped out on its own.
I had hoped I could fuck him but he said he had just started to use the second size butt plug. "It's pretty uncomfortable and it's not as big as that lovely cock of yours," he said. "So let me suck it and I'll give you a call when I'm ready because I'm really looking forward to having a real cock up there."
My second time being sucked was every bit as good as the first, maybe because I wasn't nervous about trusting my precious cock into a strange mouth full of teeth. That and the fact that I lasted a little longer than my maiden voyage. That gorgeous escalation of sensation that is the precursor of ejaculation was a little longer this time. When I asked Tim to slow down he did, and his sucking stopped, replaced by just his tongue lavaging my glans. Such a disparity of feelings: I desperately wanted to cum, needed to cum, but I didn't want this intense feeling to quit either. Then Tim put his finger up my greasy pucker and that did it. "I'm gonna cum, oh God I'm gonna CUM!" I said. Tim lifted his head off to watch but kept his finger busy in my rosebud.
POW! The first jet raced through my straining cock with such intensity it felt more like a hot solid than liquid. It arced about a foot in the air and we both watched my penis dance and spurt. My belly was covered in dripping cum but I was indeed a happy camper.
I asked Tim to loan me his smallest butt plug and he did, promising to let me know when his asshole was ready for my cock.
The support group was in session, the new members had been introduced. He had started his opening talk on the legal status of gay marriage in the various states and courts when a very pretty woman about my age walked in, went to the adjoining room to undress and walked out to take her seat. Whoa! The lady was swinging a very nice dick! Strawberry blonde with a little patch of matching curly hair over an otherwise shaved pubis. Gorgeous. I couldn't take my eyes away.
After his talk the moderator saw me and said, "At the last meeting you told us you hadn't decided you were gay or not. Have you made up your mind yet?" I answered in the affirmative. "Well, since you came back to join us I assume you have concluded that you are in fact gay," he said. I nodded with a broad smile.
The meeting over and it was coffee hour. Two guys were talking to the luscious blonde and I joined them, put out my hand and said, "Hi. Dan Petersen."
"Dani Olsen. How about that, names match and ancestors both from Scandinavia." Her handshake was firm, the smile was hypnotic and I was in love. The other two guys peeled off and I offered to buy her a drink on the way home. "Fine, but just a quickie, I've got homework to do. I know a nice little place on the way home so why don't you follow me there?" She said. It was a nice old fashioned tavern, pretty quiet with an old guy playing old favorites on the piano in the corner. She had a Coke, I had a draft beer and we talked. She was on the finishing touches of an MBA and learning a new job. Her voice was low pitched for a girl and sexy as hell. I told her I was a newcomer to the gay scene just having accepted being "one of the family" and asked when she had made her transition.
"From as far back as I can remember I felt like I was a girl in a boy's body. My mother was very understanding but Dad took longer to accept it. He was a jock in school and had hopes of raising me into the world of athletics but he finally came around to reality. When I reached puberty they enrolled me in a private school in a neighboring town and I entered as a girl." I wanted to know when she began the hormone replacement thing and she said, "That,was a little more complicated, but I really need to hit the books tonight so I need to get home."
I had checked the menu as we talked and it looked pretty good so I asked her to come back Saturday night for dinner and she agreed to meet me here at 7 PM.
Tonight she was dressed up a bit more than at the meeting. A light green sheath dress that complimented her slim shape and heads turned when she walked in. Same piano player and a little more lively. A few people were dancing and after we ordered, while we were waiting for our dinner we joined them. She danced as nicely as she looked. Not close, but not distant either. The meal was good, her choice of wine was the same as mine and it was chit chat as we ate. When we finished, she said, "I'm curious. In the meeting you indicated you had decided you were in fact gay. What made your mind up?"
I told her the meeting helped, because I'd never been around a collection of gay folk before and I felt comfortable and part of the group. And I added that I had met a guy there and we had gotten together. "And?" She said.
"And we had sex," I said. She wanted to know what kind and I hesitated, then said, "Give and take oral. It blew my mind, no pun intended." She giggled at that and said, "Understood. I'll never forget my first time either." I wanted to ask her what that included but she didn't volunteer and I let it pass.
"I'm curious. You have developed a lovely pair of breasts and definite female curves so you must have been taking female hormones. But I know two guys in my workout group who have been on estrogens since developing prostate cancer and both now have penises that have shrunk to mere nubbins. But you have a very generous one so I don't get it."
"I didn't begin hormone therapy until well into puberty and by then I'd figured out how to have orgasms. I wasn't about to give those up so I opted for combination male and female hormones." I asked if that meant her penis was functional. "Yep, my clitoris is fully functional, thank God," she said. "But I haven't had much, er, other people sex."
"Typical girl, you have to be excited between the ears before anything good happens," I said.
"Dani laughed," and said, "Maybe you're right, let's dance." This time we danced close and soon he felt a firmness poking his pelvis. Was it wish fulfillment or a boner, he wondered. It was closing time and as they left the dance floor there was a distinct bulge in her dress. As they left he started toward the parking lot but she said, "I didn't drive, I walked. My apartment's two blocks away." So they walked there holding hands like teenagers. When they got to her door she said, "Thank you, that was a lot of fun." I said it was fun for me too and asked if we could get together the next night, Sunday. "Call me tomorrow afternoon and if I can get my homework done, it's a date."
I turned to leave and quietly, she said, "Aren't you going to kiss me good night?"
TO BE CONTINUED