I Get a Girlfriend (and more)
When I turned 16, my dad got me a car - a brand new Mustang Cobra and I had a lot more freedom. I also got a lot more attention from girls. I was at a school dance and a stunning girl came up to me and asked me to dance. Her name was Dannie (Danielle) and she lived a few blocks from me. I had met her a month earlier when her family moved into the neighborhood. They invited the neighbor kids to a pool party so Dannie could make friends quickly. I didn't think she even noticed me. I spoke to her father more than I did her. She was a beautiful redhead and had a great body. Her tits were D cup (at 16) and she had light blue eyes.
We danced a slow dance and she was really holding me close. I wasn't sure, but it felt like she was rubbing her breasts against me intentionally. We danced several times, all slow dances, and she asked me to take her home. I quickly agreed and when we got to her house, she invited me in for a swim. I told her I didn't have a suit and she said I could borrow one from her dad. I agreed and her dad was very nice about loaning me the suit. We went for a long swim and she turned the lights out on the patio. She kissed me and we necked for a while. I wanted to go further, but this was new territory for me. I had never had to do the romance thing before. Jaden always said I gave off a strong sex vibe and Hal agreed when I told him. They both said I had a real feminine side. That night with Dannie, I was a different person.
We began dating and my Friday nights changed dramatically. I was always out with Dannie on Fridays, so Jaden and Carson were cut off. After a few dates, I made my move with Dannie and she responded eagerly to my advances. We had sex in her pool the first time. It was very erotic knowing that her parents were only 50 feet away while she sucked my cock and I ate her hot cunt. I fucked her once that night and was amazed to find that she was a virgin. Despite that, she was a fast learner. We worked hard to find times and places for sex and eventually she let me fuck her in the ass. After that, she couldn't get enough. She also learned to swallow cum and deep throat. When I taught her to do it, I told her that I learned from watching a previous girlfriend. We managed to have sex about twice a week.
Jaden was getting more than a little testy about getting cut off, but he understood. We managed to fuck occasionally on weekends when his parents were out of town. I always wore makeup and lingerie when we had sex and he loved calling me bitch, cunt, slut, and whore while he pounded my ass or filled my mouth with his hot cum. One Saturday, I forgot I was supposed to pick up Dannie early and Jaden had just fucked me and cum in my mouth when I remembered. I barely had time to change and rush over to her house. When Dannie's father answered the door, he looked at me strangely as he invited me in. I didn't think twice about until I went to the powder room and looked in the mirror. There on my cheek was a bit of cum and I still had lipstick and mascara on. I was sure he didn't see the cum or didn't know what it was. The lipstick and mascara were hard not to notice.
I washed up and came back out, wondering what he might say. He wasn't around though and Dannie came down and we left. We had to go to a motel that night to fuck after the movie. I was fucking her ass when she started to laugh. I asked her what was so funny and she told me that she had caught her father fucking her mother's ass a couple of days before. She said they were very cool about it because they were always so open and accepting about sex. I told her that they might not feel that way if they caught me fucking her in the ass. She laughed and said that they knew we were having sex. I laughed, but then realized that she was serious. Then I panicked. I thought I was a dead man, but she said that they were cool about it. I had trouble believing it, but she assured me that it was OK. She told me that they belonged to a swingers' group and had even hosted a party once while she was at her grandmothers' house for a visit. Her parents had not told her about the swingers' group, but their housekeeper spilled the beans. Her father is a well-known surgeon and I was surprised that he would risk his reputation like that. It's amazing to me the risks people will take to satisfy their desires, me included.
The next day, I stopped by to return the swimsuit that I had worn home that first time and had promptly forgotten about. No one answered so I walked around to the pool and saw her father tanning. I said hello and he shook my hand. I handed him the suit and he told me to put it on and join him. I asked where Dannie was and he told me that she had gone shopping with her mother and wouldn't be home for a while. I decided I should be diplomatic, so I put on the suit and joined him by the pool. He handed me a gin and tonic and I took it, a little surprised, considering my age.
After a bit of small talk, Howard said "My daughter tells me you are great in the sack." I dropped my jaw and my drink at the same time. When I reached to pick up the pieces, I cut my hand. He told me to follow him inside so he could put a bandage on it. I tried to apologize about Dannie while he put the bandage on but he said "David, Dannie is very much like her mother, a very sexual young woman. It's perfectly natural. Her mother and I are very open sexually. In fact, we have sex with other couples. Does that surprise you?" "Yes it does," I lied. I decided to be bold and asked "Does Dannie's mother have sex with other women or just men?" "This intrigues you doesn't it David?" he asked knowingly. "Yes she does, it's very erotic. I love to watch her with other women or have sex with another woman while she joins in." I decided to really push my luck and asked "Do you have sex with other men too?" He looked serious for a moment and said "No David, I never have, although I am interested. Carol doesn't want me to. I know that sounds odd, since she has sex with women, but she said it would really bother her. Some of the guys in the group do have sex together and she doesn't like it. She won't do a threeway with two men if they are doing things with each other." The conversation had definitely gone way beyond anything I would have expected.
"David, how long have you been having sex with men?" he asked. My jaw dropped again and I said "Where did you get that idea?" He told me that he had noticed the makeup the other day. I tried to make something up quickly, but he stopped me and said "David, don't worry about it. I won't tell Dannie. I don't think she would be any more open to it than her mother." I decided to come clean and I told him that I did enjoy sex with men occasionally. He laughed and said that I should be more careful about the makeup and that he was probably the one father that would have let me in the house. I laughed, thinking about Carson, but didn't say anything.
We went back to the pool and he asked me to put some suntan oil on him. It seemed like an odd request, but I decided to do it since he had been so understanding. I put it on almost everywhere, admiring his great tan and decent physique. He was in pretty good shape for 42. He looked younger than his wife and she was 38. I began to get suspicious when he slipped off his suit and lay on his back. He said that he wanted to get a full body tan. He encouraged me to do the same. I told him that Dannie and Carol might come home and see us. He assured me that they would be gone for hours so I reluctantly went along with it.
I lay on a lounge chair and he got up to fix us another drink. As he walked over and back, I fixated on his nice ass and his luscious cock. It was one of those big veiny ones and his pubic hair was shaved, making it look even bigger. I started to get hard and I covered myself with a towel. I was very embarrassed. He sat next to me on my chair and handed me my drink. As I took a sip, he lifted the towel and saw my big, hard cock. He rubbed it and said "I see why Dannie likes you so much. This thing must really do a number on her." I was perplexed by his attitude toward his daughter, but I was so excited I quickly forgot about it. He started stroking me and I moaned anxiously. He leaned down and kissed me deeply while continuing to stroke my big cock. I was so hot I would have done anything for him.
"David, I want you to suck my cock and let me fuck you," he said "Will you do it?" I didn't respond. I just reached out and grabbed his big dick. He smiled and helped me up. He walked to the edge of the pool and sat with his legs dangling in the water. I dove in and stood between his legs. I licked his asshole while I stroked his cock - then finally took the head in my mouth. I gave him an incredible blowjob with lots of deep throat action while I fingered his asshole. He kept rubbing my head and calling me his "sweet little cocksucker" and his "oral angel". I thought it was strange the way he treated me like a girl, but I actually liked it.
When he finally came, I swallowed some and let the rest run down my chin. He leaned over and licked it off, tasting his own cum. He said it was his first taste. We swam for a while and he picked me up and carried me around in the pool. He kept kissing me and calling me "sugar" and "honey". It was exciting. When he got hard again, we went inside to his bedroom and he put some of Carol's sexy lingerie on me from their swinger parties. She had all of the usual "whore" clothes. He also helped me put on makeup, a necklace, and earrings, then kissed me and carried me to bed. He laid me on my back and prepared to mount me in the missionary position. He put a condom on and lubed me good with his fingers. Then he slowly pushed his way inside my ass, being careful not to hurt me. He rested on his elbows as his hips bucked up and down, burying his big cock deep in my ass. He leaned over and wrapped his tongue around mine and kissed me deeply. He never broke his rhythm as his balls slapped my ass and his cock explored my inner warmth. He kept telling me how wonderful my tight cunt was and how much he loved fucking it.
Then suddenly he got up and went to a dresser and came back with a long, thick double-headed dildo. He lubed it and stuck it up my manpussy. He said he wanted to see how far it would go in. It felt great, but started to hurt as it went deeper. I had no idea how far it could go. When he hit a certain point I yelped and he stopped. When he measured it, it was almost 14 inches in. I asked him not to go that deep again and he promised he wouldn't. Then he did something more unexpected. He stuck one end of the dildo in his own ass. He said he had done it before. We scissored each other and pushed it up both our asses. I had about ten inches up me and he had about eight and our balls were rubbing each others. We then started bucking against each other. It was so sexy.
We then got on our knees and reinserted the double cock. We faced in opposite directions and fucked each other with the dildo. It was impressive how much he took considering he had never been fucked by a man. He then removed the dildo and asked me to lie back again, which I did. Instead of fucking me more, he straddled me and sat on my big dick. He started bucking on me, really riding my cock. For an anal virgin, he could really take it. He must have used those dildos a lot. Suddenly, his cock erupted, spewing cum all over my face and chest. For a second orgasm, this was a lot of cum. I licked some off my face as he slowed his pace on my cock. He swung around, removed my condom and took my cock in his mouth. I moved him over me so I could clean his cock while he blew me. A minute later I nearly blew the back of his head off with my orgasm. He gagged on it but kept sucking till he swallowed it all. Meanwhile I finished my cock lunch.
We went back to the pool to wash off. He slipped on a condom and picked me up, face-to-face as I wrapped my legs and arms around me. We were almost chest-deep in the pool so there was not much weight on his arms. I leaned back to give him enough angle and he sat me on his cock and proceeded to impale me all the way. Then he bounced my butt all over the pool, calling me his "anal princess" and "sweet cunt girl" -- names that sound sexier in the heat of the moment. He came up my ass then removed the rubber and swallowed his own cum. I asked him to share and he kissed me, giving me a good load of my own.
We got cleaned up and had another drink. By the time the ladies arrived, it all seemed like a wonderful dream. I got dressed and Howard said he wanted to treat Dannie and I to dinner. He handed me $500 and whispered, "Take her to a nicer hotel and get room service." That night we had lobster and great sex at the Albion in South Beach. Her mother was pissed when we got home at 1:00 AM but Howard calmed her down and said he would have a chat with me. When I left, Howard walked me out and got in the car with me. "Carol thinks I'm scolding you, so look penitent." he said as he pulled out my cock and stroked it. "I want to see you again if it's OK." I agreed and asked if he would be interested in meeting the guy who fucked me the day I showed up in makeup. He said he would love that.
The next Saturday afternoon, Dannie and Carol went shopping again and Jaden and I came over for some fun with Howard. Howard and Jaden really hit it off and we had a great time. They put me in one of Dannie's short skirts and halters and took turns fucking my ass against a wall with the skirt flipped up. They kept switching off like a tag team wrestling match. We fucked in every possible combination. My favorite was when I fucked Howard while Jaden reamed me out good. I must have swallowed six loads that day and I came three times, once in Jaden's mouth and twice in Howard's. That night, thanks to Howard, Dannie and I went out in style again and I fucked her ass just like I fucked her Dad's. It was surreal. What was it about me that brought out this hidden side of men -- men who were happily married for years? Howard said I should have been born a woman because I made him feel the way he felt toward women. Based on my experience, about 10% of the population is gay and another 40% is bisexual under the right circumstances. I am constantly astounded by the seemingly straight guys that end up in bed with me, with their cock buried in my butt.
For the next few months, my dance card was pretty full. I continued to have sex with Dannie, Jaden, and Howard as often as possible. Bobby came for a visit and we ended up having sex with Jim at the video store. He had finally admitted his bisexuality and was making up for lost time. He even let me fuck him once. After that I stopped by the store occasionally for a quick fuck or a blowjob. Even Uncle Hal came to town every couple of months and reamed me out for old time's sake.
If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it. I am very interested to compare your account with her journal entries.
Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser, and Olympiad), and my own true story (Shocking Encounter).