World's Hottest T-Girl -- Part 3
The Plot Thickens
The following Friday, Jaden and I had lovely sex, with a new twist. Jaden had purloined some stockings, a bra, and crotchless panties from his mother's dresser. He asked me to wear them while we fucked and I agreed. I loved imagining his mother in them and fantasized about fucking her and sucking those big tits (Relax, you perverts, I never got to have sex with her.). The feel of the stockings was incredible and I was amazed at the way the bra made me wish I had big tits to fill those cups. I was a bit uncomfortable with the way these feminine feelings crept in. It seemed so natural.
That night, we finished with him in my ass. When he started to pull out, I stopped him. I positioned us in a spoon position with his cock still buried in my ass. I told him to leave it there and he did. I drifted off, but awoke a while later to the feel of his hard cock sliding in and out of my ass. He lifted my leg to get better penetration and really fucked me hard. I loved every minute of it. My favorite part of the night was when I fucked him, wearing his mother's lingerie. It was so erotic. I realized, eventually, that he had a real hardon for his mother, but couldn't admit it. This was the closest he could get to fucking her.
At breakfast, I kept staring at Jane and feeling guilty. I had fucked her son, sucked off her husband, worn her sexy panties, and lusted over her big tits. I just felt bad about it. Then Carson told Jane that he needed to take their motor home in to have something done on it. He told me he would drop me off on the way. Of course, even as naïve as I could be at that age, I knew something was up.
Their motor home was one of those really expensive types that cost more than most homes. As soon as we pulled out of the driveway, I knew what he had in mind. He finally worked up the nerve to ask if I would have sex with him and I eagerly agreed. He told me that he had listened outside Jaden's door while his son fucked me and had to fight to keep from breaking down the door. He said he had gone back to bed and buttfucked Jane all over the bed. I would have paid big money to see that. That's when the idea hit me. I told him I would only have sex with him, if he could somehow arrange for me to watch him fuck Jane's ass. He hesitated until I reached over and stroked his dick. As I expected he caved in quickly. We pulled behind the shopping center and climbed in the bed.
It was very hot with him because it brought out the lust he had kept bottled up for 17 years. We did it all -- blow jobs, ass licking, assfucking, 69, cum swallowing, etc. He couldn't get enough. His ass was not as tight as Jaden's because he used one of Jane's vibrating dildos on it when she was not around. Hal was out of town that day, so we had plenty of time. I let him fuck me twice and swallowed his cum both times.
When we finished, he drove me home. On the way, I masturbated him and we planned my voyeur party. We agreed that Wednesday would be the best time, because Jaden would be at his regular Key Club meeting and Carson could get me in position before Jane got home. I really believe that he was getting aroused by the idea. Their bedroom had his and hers closets and he could put me in his where I could have a good view of the bed with the door slightly open.
Everything worked beautifully. I had to wait a long time because she stopped at the grocery store on the way home, but when she got there, he was able to get her aroused very quickly. This was always a "sex night" for them because of Jaden's meeting schedule. Jaden couldn't miss because he was the vice-president. They got busy immediately and it was everything I dreamed it would be. Her body was exquisite and the sight of her sucking his cock and her tits bouncing when he fucked her was priceless. I groaned once, but she was moaning so loudly that she didn't hear me.
Finally he got her on her knees and slipped it up her sweet ass. Then she stuck a vibrating dildo in her pussy. After a couple of minutes of watching his big dick pound her ass, I shot a huge load all over the inside of the door. I kept stroking as he fucked her and eventually started to get hard again. When they finished, she went to take a shower. The sight of her getting up with cum running down her legs and shining on her face and tits was breathtaking and my dick got amazingly hard.
Carson opened the closet door and asked me what I thought. I told him that he could fuck me any time he wanted. He saw my hard cock and went down on me right there. I told him that I had to leave before she caught us. He said that she always stayed in for at least 15 minutes and we could hear the shower stop. I reluctantly let him continue, half-hoping that she would catch us. I shot a load down his throat and hurried out. Afterward, I felt very guilty about using Jane in that way. I decided I would never do anything like that again.
The following weekend, he could not use the motor home story again so I took him to my motel and fucked his brains out. Later that day, Hal made me tell him about it while he fucked me. I got this brainstorm that we should get together with Carson or Jaden, but Hal was reluctant. He was afraid that word would somehow get back to my parents and he would be in big trouble. I decided to let it go -- for a while.
I Get Caught and Make New Friends
On Moday, at school, this tall skinny kid named Bobby took me aside and said he had something important to ask me. I didn't know him well, so I was surprised when he asked "Are you a male prostitute?"
"Of course not." I said, half-stunned and half-angry, "Where did you get that idea?"
"My dad owns the P______ Motel and I work there on Saturdays. I've seen you there with different men and I checked the rooms when you left and found used condoms. I know you're fucking around with these guys."
I knew he had me, but I didn't know what to say. Finally I asked, "Have you told anyone about it?"
"No", he said, "I wanted to hear your side of it first."
"Well Bobby, I guess I don't have to tell you that I am bisexual and I have to go to a motel because my parents would not appreciate me doing this stuff at home. For what it's worth, I've had sex with a woman there too." I don't know why I felt that I needed to add that.
"I can understand David, but you're going to have to do something for me to keep me quiet."
How did I guess that was coming? When I asked him what it was, he said I had to go to a movie with him on Saturday night. This seemed rather innocent, so I agreed.
That week, I did not stay at Jaden's on Friday, because they were out of town. Hal showed up with a surprise. He had been very excited about my lingerie session with Jaden and he brought a really slutty whore outfit for me to wear while we fucked. It had black leather boots, black fishnet stockings, a leather waist harness that held my cock in place, and a black boustierre He even had makeup, which he helped me apply. I was stunned by the transformation and so was he. I actually looked kind of hot. He kept calling me his pretty whore while he fucked my ass.
That evening Bobby and I met at the local mall. Then we got in his car (he was 16) and he drove to an adult video store. I asked him what we were doing there since we were underage. He told me the night manager was a friend of his and he went inside alone. A couple of minutes later, he came back out and we drove around behind the building to the delivery door. The door opened and we went in. We went inside a small room and Bobby told me it was a private viewing room. There was a large screen, a chair, and a small padded bench in there. I was scared, but anxious to see what would happen next.
He told me to sit and he entered a code from a piece of paper. Suddenly an adult film came on with a guy fucking a girl in the ass. I couldn't help but think of Angie and wonder where she went. I had not seen her since that day at the motel. I would have asked Bobby, but I didn't want to get her in trouble.
I started to get hard watching the film and then a new character appeared. It was another guy and he slid in behind the first guy and slid his cock up the guy's ass while he was still fucking the girl in the ass. For some reason, I had never considered that position, but I found it incredibly erotic.
Suddenly Bobby got up and slipped his clothes off. I almost fainted when I saw his cock. This skinny kid had an enormous slab of beef hanging from his crotch. It was soft and it must have been almost eight inches long and three inches wide. It looked so out of place on that skinny body. He started to stroke it and it must have been almost ten inches when it got hard. It never got above parallel to the ground because it was so heavy and his balls looked like oranges.
I was starting to feel a little strange because he had not told me what he had in mind. That big dick was certainly worrying me, but it was intriguing at the same time. He said "Watch this." and turned toward the wall and stuck his finger through a hole that I had not noticed before. I had no clue what he was doing until I saw a 6-inch cock slide through from the next booth. Bobby immediately went down on it and started sucking it like a baby. It was so odd to think that some anonymous man was in the next booth getting his dick licked by an anonymous tongue in our booth. Bobby stopped briefly and handed me a condom and some lube. He motioned for me to fuck his ass and I was ready, willing, and able. I slipped in easily and started a steady rhythm while he continued to suck the other guy. Soon the mystery man exploded in his mouth and he shared some with me. It was sticky and not too salty.
Bobby then had me stick my cock through the hole. I did so reluctantly, a little afraid of what might happen. I expected a hand or mouth to greet me, but instead I felt the unmistakable feel of a woman's pussy enveloping my cock. Bobby got down behind me and started licking my asshole while this woman squeezed my cock with her pussy muscles. Then I felt a tongue on my cock, licking me and the woman's cunt at the same time. It was fabulous. I was feeling sensations everywhere and then Bobby really surprised me. He stood and placed his cockhead against my sphincter and pressed forward. I felt intense pressure but it wouldn't penetrate. He tried a couple of times, then started inserting fingers up my ass. I moaned loudly as he inserted the fourth finger.
Then he pressed his cockhead forward again and penetrated with his huge mushroom. I grunted, feeling like I had sat on a telephone pole. He let me rest briefly, then pushed a few more inches in. Thank God he had put a lot of lube on the condom. He stretched me to record widths and took my breath away as he plunged in further. When he finally bottomed out, I thought his cock was in the back of my throat. It was so intense that I almost forgot about the cunt that was massaging my cock and the tongue that was bathing it.
Suddenly the pussy and tongue were gone and my dick stood harder and higher than ever. I then felt a new tighter grip on my cock as someone was inserting it in an asshole. I reached through the glory hole with my finger to rub her pussy and touched balls instead. It was a man's ass and the woman started licking my cock as he fucked himself on my stiff shaft. Bobby started moving his cock in and out of my ass slowly, pushing me deeper in the man's ass. I heard moaning from the other booth and the woman stopped licking my cock. I could feel a pulsing around my cock and heard sucking sounds. I realized that he was coming and she must have been swallowing his jism. This was so kinky not seeing the other couple.
Bobby was moving faster now and I was starting to feel a buzz in my balls. The feeling was still intense, but very exciting. Bobby called me his bitch and, for some reason, it excited me. The mystery man started fucking himself even harder on my cock as Bobby picked up his pace. Being the meat in this sandwich was fantastic. I finally couldn't take anymore and started humping faster. The mystery guy, pulled off and the woman swallowed my cock. The man then started licking the shaft while she sucked the head. I exploded in her mouth and then they switched so he could finish swallowing my cum. It was an incredible orgasm. I must have pumped a gallon of cum. Then Bobby started short-stroking and blasted his load up my ass. I could feel the heat of his semen as it filled the tip of the condom. He kept stroking for a while then slumped on the bench. I turned around, my ass feeling so wide open from the huge cock that had bitch-fucked me. I carefully removed the condom and emptied it into my mouth. Then I leaned forward and kissed Bobby, sharing his cum with him.
There was a knock on the booth door and I was frightened. I pictured the vice squad at the door. Bobby laughed and opened the door and in walked two gorgeous women, both in short skirts. I was very excited, but did not understand what was happening. Bobby noticed my confusion and laughed loudly. He finally told me that they had been in the next booth. I was relieved but wondered, out loud, where the man had gone. One of the women laughed and lifted the skirt of the other woman, revealing a 6-inch cock. I was astounded and aroused at the same time. I had heard of shemales, but had never seen one, even in pictures. She (he?) was very attractive and had big tits. It was fascinating and I studied her carefully. She introduced herself as Shelly and introduced her friend as Sapphire a stripper at the club next door. I stupidly lifted her friend's skirt just to be sure. They both laughed.
Shelly said she could just eat me up and proceeded to prove it by going down on me. Bobby rubbered up and planted his cock in Sapphire's cunt. They shifted with him laying on the bench while she rode him "cowgirl". I lay on the floor and Shelly moved into a 69 position so I could taste her big clitstick. We really went at it and eventually we both got a mouthful. I sat back and rested, watching Bobby and Sapphire go at it. Shelly moved me to my hands and knees and slipped on a condom. Her cock was already hard again. She called me "pussy boy" and slipped her cock up my ass. After Bobby's big log, I wasn't sure that I would feel it, but my ass had closed a bit by that time and Shelly's cock felt wonderful.
Sapphire then had an inspired idea. While she sat on Bobby's schlong, she had me straddle the bench and buttfuck her while Shelly slid behind me and mounted me. It took a while to get everyone positioned well, but it was very erotic and worked fairly well. When Shelly got close, she moved around and exploded in Bobby's mouth and on his face. Sapphire leaned forward and licked his face clean. Then Shelly moved in and started licking both of the cocks that were buried in Sapphire. That caused us to cum much sooner and I ripped off the condom and shot my load on Sapphire's ass and pussy, covering Bobby's cock in the process. Then I moved down and licked it all up. Bobby pulled out and I removed his condom and slipped that huge member in my mouth. I worked up and down the shaft with my tongue and lips. When I deep throated him and took the whole thing he blasted me with his load. He was so deep that most of it went down my throat immediately. I pulled off halfway and tasted the rest.
Bobby told me that no one had ever taken even close to that much of his cock. He was amazed and very pleased. By now it was getting late and we said goodbye to the ladies and left. When we came around to the front of the place, the evening manager was waiting for us. Bobby pulled up and let him in the backseat. He introduced himself as Jim and told me that he had watched most of the action through a peephole. I was a bit irritated until Bobby said that it was part of the deal to get us in. I asked him what the rest of the deal was. He pointed to the backseat where Jim's cock was waving in the breeze. He told me that I could do the honors or drive while he did. I told him that I couldn't drive yet and he said that it would have to be me. I would have been really angry, but Jim was very attractive and had an uncut cock, which I had never had before. I climbed over the seat and started to kiss him, but he pulled away. "I don't go for that stuff," he said, "I'm not a fag." I was stunned and didn't know what to do. "I just let queers suck my cock and I fuck them." Talk about major denial. I really didn't mind, but his attitude pissed me off and I decided to do something about it. I told him to take off his pants and underwear so I could do it right. He reluctantly did so and I started sucking his cock. It was strange the way his foreskin moved back and forth but he really got into it, grabbing my head and facefucking me hard with his 6-inch cock. I moved my hand to his balls and rubbed them as he moaned deeply. Then I snuck a finger to his asshole and pushed. I managed to get an inch up his ass and he came unglued.
"What the fuck do you think you're doing bitch?" he screamed. "I'm not into that shit." Then I said, "You are if you want me to finish." He was pissed. "Bobby, get back here and suck my cock. This queer wants to make me into a faggot too and I ain't goin' there." Bobby laughed and said, "Jim, it's time you faced the fact that when you have sex with men, you are at least bisexual." Jim looked as if Bobby had just cum in his mouth. He couldn't speak.
Finally he started to cry and said "My father always said I would turn out to be queer. Then I came home early from school one day and found him getting fucked in the ass by a queer that lived down the street. That bastard made me this way. I can't help myself." This whole evening was just full of surprises. I told him to calm down and I hugged him while he sobbed. This had obviously been building for a long time. We drove him back to get his car and we never finished the sex. He kept apologizing and told Bobby he was still welcome in the booth any time. When Bobby dropped me at home, he told me that I was welcome to join him anytime and he would love to join us for a threesome at the motel sometime. I told him I would think about it and kissed him goodnight.
I finally did introduce Bobby to both Hal and Carson. They both agreed since he already knew their names from their credit card receipts and hadn't told anyone. Neither of them let Bobby fuck them with that monster cock, but he fucked me several times. Then Bobby's father sold the motel and moved to Birmingham, Alabama and Hal was transferred to Atlanta. Bobby eventually moved to San Francisco because the scene in Birmingham was not conducive to people with his proclivities.
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).