Enter Jaden
When I turned 15, I went to high school as a freshman. The first day, I met a guy named Jaden, who was about 6' 4" tall with sandy brown hair and piercing blue eyes. I was 5'7" then and haven't grown since. Jaden was trying out for the basketball team and I immediately decided that the basketball team needed another trainer. The thought of wrapping those tall hunks with tape was a perfect job for me. My interest in girls was just as strong, but guys were easier to see naked in the shower (without getting arrested). I went to see the coach and he immediately agreed, since his previous trainer had graduated and he was looking for a replacement.
It was everything that I hoped it would be. Naked, athletic bodies everywhere. Guys needing their muscles rubbed and little old me there to oblige. I especially enjoyed it when Jaden got a pulled calf muscle and I had to rub it down while he lay on his stomach. I got hard just looking at him that way.
One Friday, after school, Jaden invited me to come over to his house for dinner and a late movie. I told him that Uncle Hal and I played golf on Saturday mornings. He said I could sleep over and his dad would take me home the next morning. I agreed (thank you God) and met his family that night. His father, Carson, was 39 and still in good shape. His mother Jane was a beautiful woman with big tits and a great ass. I got aroused watching her walk across the room.
That night was uneventful, although Jaden and I slept in the same bed and I spent half of the night trying to figure out a subtle way to suck his big dick. His cock was in proportion to his large frame. It was slightly larger than mine and very thick. I just couldn't work up the nerve. The next day, Hal didn't know what hit him. I was so horny, I fucked him senseless.
Friday nights at Jaden's became a regular thing. He invited me almost every Friday and I always accepted. By the fourth Friday, I was desperate to try something. I brought over some of my father's port wine in my overnight bag and talked Jaden into drinking some before bed. By the time we went to sleep, he was definitely intoxicated. We went to bed about 1 AM and an hour later I made my move. He had just turned over on his back and was sleeping soundly. I reached down and slipped my hand in his briefs and started stroking his cock.
Jaden started to writhe and moan but didn't open his eyes. I kept stroking and he got so hard. I decided it was now or never and I moved down and took his cock in my mouth. I didn't know what to expect and I was afraid he would punch me. Instead he held my head and started thrusting into my mouth. I really worked that cock over well. When I swallowed it all he began rubbing my hair and groaning. I knew he would not last long and I wanted it to be very special for him. I began bobbing and sucking, stroking and milking him. When the first spasm erupted in my mouth, he let out a very load groan. I was terrified that his family would hear him. He bucked his ass feeding me his cum as his cock pulsed in my mouth. When he finally finished, he whispered, "Thank you" and turned away to sleep. I was confused, not knowing how he felt.
The next morning he didn't say a word about it and his father drove me home. Hal and I had great sex that day, but I couldn't stop thinking about Jaden's reaction. At school that week, he acted as if nothing had happened and when Friday came, he invited me to stay over again. When I hesitated, he winked at me and said "Bring the wine again." My dick got hard just thinking about the night to come. As soon as we turned the lights out that night, he slipped out his huge slab of meat and offered it to me. I accepted it quickly and started working him over, rubbing his balls, squeezing his shaft with my soft lips, and squeezing his ass with my hand. After a few minutes, he pushed me away and asked if he could fuck me. I tried to contain my excitement, but quickly agreed. I got a rubber from my bag and slipped it over his thick shaft. I lubed my ass and his cock and told him to go easy. I had never had a cock this big and I was nervous.
He was gentle as he prepared to mount me. He wanted me on my back so he could watch my face and I was happy to oblige. He pressed his cockhead against my tight hole and penetrated me carefully. My cock grew harder as my ass stretched to accommodate his thick love log. He pushed slowly, rocking a little, until his balls rested against my ass. He was going too slowly for me and I hissed "Fuck my ass with that big dick, you stud." It was corny but it got him going. Before long he was moving in and out like a jackhammer and I was in heaven. My knees were pinned back against my chest and his balls made a slapping sound as they bounced off my ass.
When he was ready to cum, I told him I wanted to eat it, but he really wanted to shoot in my ass, so I let him have his way. When he shot his load, I could feel it pulsing in the rubber sheath that was buried in my ass. He let out a loud yell when he came and again I feared that everyone must have heard. He fell on my chest and, to my surprise, kissed me deeply, his tongue exploring my mouth.
When he rose, I thought he was going to sleep. Instead, he began stroking my cock. Then, to my surprise, he took me in his mouth and started sucking my dick. I was stunned, but very pleasantly so. He was not bad for a rookie and he was able to take most of my cock without gagging. I was eagerly awaiting my orgasm, when he pulled off, leaving me hanging (Ok, standing straight up). Before I could protest, he leaned over and whispered, "Please fuck me David. I need to know how it feels." He was just full of surprises!
His big cock gave me an idea. I lay on my back with my head and shoulders raised by pillows. I slipped on a condom and instructed him to straddle me and place his sphincter against my cockhead. He pressed slowly against my cock until, finally, the head penetrated his ass. I then moved forward with my plan. By bending and pushing my shoulders forward I was able to get the head of his prick in my mouth and suck it while he impaled himself on my hot sausage. He was happily surprised and it took his mind off the painful stretching his ass was enduring as he lowered himself on my log,
Once he had settled all the way down, with his balls resting on my stomach, he began to buck forward, giving me more of his cock to suck. The feeling on my cock was unbelievable. Hal was tight, but this was my first cherry boy and the feeling was indescribable. The great cocksucking he was receiving encouraged him to ride my cock and he really got into it. After his sweet ass adjusted to my big anal invader, he really started to ride me. I had trouble keeping his cockhead in my mouth.
After a few minutes of this he began to moan loudly then, with a yell, he exploded in my mouth. His bucking pulled his cock from my lips and he sprayed my face with his sticky, hot cum. That really got me going and I shot a huge load in the condom that was lodged in his tight butt. He removed the condom and licked me clean, then flipped over and prepared to sleep. I curled up behind him, reaching around to fondle his big cock while he drifted off.
In the morning I went to the bathroom that was connected to his bedroom and climbed in the shower. A few minutes later, he climbed in behind me and began to rub soap all over me. His cock rose and grew hard as a rock. Without a word, I leaned forward and placed my hands against the tile. He rubbed his cock with soap and placed it at my entrance. Leaning forward, he penetrated my manpussy and began to ream me good. It was like a wonderful dream. He held my hips and steadily slid his thick, hot slab of cockmeat in and out of my steaming, tight ass. I began to push back to meet his thrusts, forcing him all the way in as his balls bounced off my backside. I began to talk dirty to him, telling him how big his cock felt in my ass and urging him to fuck my ass like he would a girl's pussy. He got very excited and told me that I was better than any girl he had been with. When he came, I swung around and swallowed every drop. His groaning was so loud that I was sure everyone in the neighborhood had heard.
After breakfast, his father and I headed out, but didn't go through the usual smalltalk ("How's school?", yadda yadda, etc.). He was very quiet and I got a strange, uneasy feeling. Finally he asked, "How long have you and Jaden been having sex?" I just froze. I didn't know how to respond. He finally said, "It's OK David, I'm not angry. I understand how it can be." I started to mutter an apology, but he interrupted and said "When I was in college, I had sex with men and women, but when I married Jaden's mother, I decided I would forget about men forever. I have not touched another woman or a man since, but when I heard the two of you going at it through the door, some old feelings came back. I got so aroused hearing the two of you that I went back to bed and fucked Jane like a madman. She didn't know what hit her." I was amazed at the things he was telling me and I didn't know how to respond. I just stared and waited for him to get to the point.
Finally he asked, "Is Jaden gay?" I told him that both Jaden and I were into girls too. That seemed to relieve him. Then he asked, "Was Jaden your first man?" I told him that I had been with others (OK, I exaggerated), but I wasn't about to tell him that I was on my way to fuck my uncle who had been fucking me for months. He then told me that, although he had never been with a man since he got married, he had always felt that something was missing. I told him that I understood that feeling. He then asked the $64,000 question, "Would you be interested in doing something with me?" It felt strange to admit it, but I told him I would love to suck his cock. He looked so happy, I almost felt sorry for him. I leaned over and unzipped his pants. He looked like a deer in the headlights. I reached in and pulled out his cock, which was six inches soft. I started to stroke it and he almost drove off the road.
He suggested that we pull behind a shopping center that was not open at 8:30 on a Saturday morning. After we parked, I immediately took him in my mouth and started working him over, sucking and licking while his cock grew to its full eight inches. He was even thicker than Jaden. He was so hot, despite having fucked his sexy wife just a few hours earlier. I knew he wouldn't last long and, sure enough, he started breathing faster and shot a string of cum straight down my throat. I kept sucking until there was nothing left to swallow. He kept rubbing my head and thanking me, then started the car and drove me home.
When we got there, he thanked me again and I went inside. When Hal arrived, we drove off and he leaned over and gave me a big kiss. He pulled back and looked at me with a shocked look. I realized that he could taste the cum that Carson had just shot in my mouth and I was very concerned about his reaction. He just grinned and asked me whose cock I had just sucked. I decided to come clean and told him the whole story. He got so hot that he made me blow him right there in the car on the way to the motel. He kept kissing me to get another taste of Carson's cum. The sex that day was hotter than ever.
After we had been at it for an hour, I was sucking Hal's cock and suddenly I realized that a maid was standing across the room, staring at us. We had not heard her knock and come in. She started yelling in Spanish and Hal freaked. I could understand enough to know that she was going to tell the manager. I jumped up and, in broken Spanish, asked her not to do it. She calmed down and told me that she had never seen anything like this. I noticed that she had a great body and started to get aroused again. When she saw my cock harden, she started to laugh. I asked her if she would like to stay and watch. At first she said no, but I talked her into it. I think she was amused and intrigued at this point.
Hal had lost his erection so he started sucking my dick. The maid, whose name I later discovered was Angie, sat in a chair and started to rub her crotch. Before long, her hand was inside her panties, then the panties came off. Remember that I had never been with a woman before and the sight of her pussy lips made me so hot. I tossed her one of Hal's dildos and she started fucking herself with it. Finally I couldn't stand it and I jumped off the bed and knelt between her knees. She was so hot, she didn't even attempt to stop me. I began licking her pussy and tonguing her and she grabbed my head, pulling me closer. The pungent aroma of her cunt was intoxicating and cuntjuice poured over my face. I motioned for her to show me her tits and she obliged, taking off her remaining clothing. Her tits were very large, at least a D cup. She kept yelling "Coma mi concha (eat my cunt)"
Hal was tired of being left out and joined us, inserting his cock in my ass and starting a slow pumping rhythm while I tongued and fingered her cunt. I knew enough to know where her clitoris was and when I started working it over with my tongue, she went wild. When she came, she covered my face with pussy juice. Afterward, I asked if I could fuck her. She agreed and slipped a condom over my cock. She knelt and started sucking me while Hal continued to fuck my ass.
We finally moved back to the bed and she lay on her back and let me slide my cock in her tight cunt. She was no virgin, but she was my first woman and it was heavenly. There is something so soft and inviting about a woman's love box. I fucked her in several positions, watching her cum twice. Then we moved into a 69 with her on top.
Suddenly, Hal's cock appeared and slid into her pussy. I continued my tongue work, licking her cunt and Hal's cock at the same time. I think they both found this incredibly erotic. She really went to work on my cock and I signaled her that I was about to cum. She pulled my dick out and aimed it at her tits. I squirted a big load of juice all over her tits. She then licked me clean and turned to straddle Hal. She leaned forward and rubbed her tits in his face as he licked off my cum.
As she fucked Hal she kept trying to tell me something. She motioned at her ass and said "Tome mi culo" over and over. I finally understood that she wanted me to fuck her ass while she rode Hal's cock. For some reason, I hesitated and she yelled "TOME MI ASNO." I decided that I had better do it to shut her up. I lubed my cock and positioned it while Hal stopped fucking. She was really tight, but not an anal virgin. It felt really great with Hal's cock applying pressure through the walls of her hot, juicy snatch. We managed to get a good rhythm going and the vision of her taking us both and loving it was so stimulating. When I was ready to cum, she motioned me to bring my dick to her mouth. She and Hal were both licking me and when I erupted, they shared my cum. I fell back exhausted, then started fingering her asshole, while she came. Hal followed quickly and Angie and I shared his cum. We rested a few minute, then she had to get back to work.
It was an amazing day. I've been involved in much more kinky sex in much more bizarre circumstances, but this day was full of firsts - my first fuck with Jaden, my first encounter with his father, my first time with a woman including oral and anal, and my first male/female threesome. I loved licking the two of them while he fucked her and I loved eating out her cunt and sucking her tits. I was in a daze for a week. I thought that sex was supposed to be like this and it changed my perspective on relationships. I have never been in a monogamous relationship and probably never will.
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).