It all started when my girlfriend wanted more adventure in our sexual relationship. I must admit I was a little naive about sex when we meet and was more than willing to experiment with the joys of sex. I was sixteen when we had our first sexual encounter and for two years we had sex in just about every way known to man. We tried S&M, B&D roll playing, and even watched videos and did what they did. If she saw a picture she liked, we tried it. We gathered all kinds of toys and by the time I was eighteen I thought we had done everything possible between two people.
Let me tell you about us first. I was a sixteen, never been kissed, country boy who thought sex was watch'en the hens and rooster on Saturday night. I moved to a big city were I first saw Linda and was captured by her beauty. Linda was one of the most popular girls in school and I thought I would never get close to her. One day I got into a fight with the school's football QB and my shirt was ripped off my back. As a country boy doing all the chores I had not needed to work out it was provided through tough work. My six pack, sharply defined muscles, and pecs were exposed for everyone at school to see. She was there and I was embarrassed. I am 6' and weigh about 160 pounds, no fat. I have brownish-blond hair with greenish-gray eyes. She stood there looking at me with almost her tongue hanging out of her mouth in shock I supposed. As I was taken to the office and sent home I almost did not want to go back to school. Although I had won the fight and in some people's eye, I was a good guy now. I did not want her to see me again nor I see her. I knew she hung around with the QB although I was told they were not girlfriend/boyfriend. I just knew that I was never going to get to be with her now. Why would she want an average jerk like me?
Linda came by my house later that day, (I still do not know how she found out where I lived) in a short blue jeans skirt, a nice white and blue blouse. Her smile was as wide and pretty as I had ever seen it. Her blond her was shoulder length and feathered back, her eyes were blue and she had on hardly any make-up. She was a beauty queen in all rights. She told me that she just wanted to check on me and see how I was doing. She asked my dad if we could go for a walk and he told her yes even though I was now grounded for fighting in school.
We walked around the block several times. She began asking me about my body and my chest. I was really uncomfortable and I guess she noticed. She also guessed I was a virgin. She told me she was going to have to fix that and I said ok not really knowing what one was. A couple of weeks later she and I had our first sexual encounter. It started with kissing and ended with her blowing me.
For the next two years we developed a sexual relationship. We never fell in love with each other as a married couple do, but wanted just pure sex.
One night about a year after our first encounter, she decided to pop in a video and do as the couples on the screen did. As we were not old enough to get the videos, we relied upon one of her friends to get it for us. I knew she was probably fucking Larry too, but he was older and I never thought much about it as long as we continued to fuck also. In this video something happened that changed my life forever. It involved two guys and a girl. The two guys were doing everything to the girl. When they got into one fucking her missionary style she gave the other a blowjob. As she was blowing him, the other leaned over and engulfed his dick from her mouth. I was shocked and stopped fucking Linda. I was not upset, just surprised. I had heard of guys doing it with guys just never seen it before. As I watched Linda reminded me that we where to follow the scene. As there was not another guy present Linda suggested that I could suck on a dildo. I agreed without really thinking this through. I sucked on the dildo and kept fucking her. I must have been really getting into it as I was ready to cum in seconds. The screen switched positions and so would we. The guy that was getting blown was now lined up behind the guy fucking. It showed him inserting his cock into the guys ass. I have had a finger stuck up my ass from Linda a couple of times and it always hurt, I could not see how this guy was going to take a huge cock up his ass. But he did and Linda was really enjoying this now, teasing me about taking a cock up my ass. She greased the dildo and to my protest began inserting it into my asshole. She had gotten a vibrating one declaring it would feel more like the real thing. It hurt like hell. I wanted to screamed in pain, instead she began deep kissing me. After a few seconds or so I got back into fucking her and she turned on the vibrator. It felt great. All of the sudden the pain was gone and I was enjoying this vibrating dildo up my ass. It kept wanting to slid out so I put on a jockey strap backwards and used it to hold the dildo up inside me. I was now in heaven. I was trying to make it last forever. I forgot all about the film and shot about six heavy loads of cum deep inside her. It had to be the best orgasm of my life. I was so excited and exhausted that I collapsed right on top of Linda with the dildo still vibrating in my ass. She kissed my neck and ear mumbling about having another guy join us. At this moment I would agree to anything, I was so excited.
It was about a week later when we normally had our little encounters and I went over to her house still thinking about the great fuck we had last time.
Without wanting to sound to anxious, how was I going to tell her that I wanted her to stick that dildo up my ass again. We did not normally do the same thing week after week, switching each day to keep the excitement going along with experimenting with new ideas.
She told me that she wanted to do B&D tonight and that I was going to be tortured. She took me over to Larry's house (which is were we did most of our sexual games). Larry has a basement that is designed for sexually active and open minded people. I have been tied to a wheel in his basement several times so this was nothing new and I was looking forward to this. Larry has never been there when we have played our games or at least not to my knowledge he was never there. This time was no different he was nowhere to be seen. Linda lead me to the basement and had me strip. She gave me a dog collar and wrist and ankle bands. She then had me put on a pair of extra small bikini brief made of leather, as always if I got hard before I finished putting everything on, I got a swipe with a frock across the hardening cock. It hurts like hell and taught you to control yourself. After I got everything on she snapped me onto the wheel in the spread eagle position. She then told me that this time instead of her torturing me she has a friend who wants to give me pleasure. She then blind folds me and tells me to relax SHE will be gentle.
I felt the hands beginning to rub all over my body. As they got to a nipple, the nipple were tweaked and pulled. Then sucked and licked. My cock was straining to break free from the leather briefs. I had to always tuck my cock in so that the head was pointing toward my ass as it got hard as not to receive to many swipes from my master torture. After licking and sucking on my nipples, the tongue was replaced with a clamp. A small weight was usually added and I waited, but no weight. It seemed like a long time had gone by and nothing was happening. I could not hear anything. Then I felt something sharp poke me in the side. It was like a knife. Then my leather briefs were cut away from me. My cock had gone soft from the lack of attention but was now on its way to full glory. Then the sound of a vibrator. I knew my ass was now going to be invaded again and I was excited. My cock was as hard as ever and I could not stop it. But how where they going to get to my ass from this position. They would have to untie me, which was alright with me, my arms were tired. However, it was not a vibrator but hair trimmers. I felt it glide across my patch of pubic hair and soon it would all be gone. I was shaved. All the hair from my balls and on up to my belly button was removed. I was then untied and moved to the table, I was bent over and then my ass was shaved. My hands were clamped to the legs of the table in front of me and my legs to the other legs of the table. I was spread eagle across the table with my back high in the air. At least this gave my arms a rest. After I was cleaned upped from the shave, some lube was applied to my asshole. I again was thinking my ass was going to be invaded. But it was not invaded by a dildo this time either. It was an enema I was to be given this time. A small tube was stuck up my ass and liquid began to flow in. As it was entering me a quick belt of pain came across my ass check. I was then told by Linda that if one drop came out before she said it could I would receive ten more just as hard. Linda was standing in front of me by her voice, so I wonder who hit me. I was sure it was Larry, but it could be anyone of her sexual friends, of whom a lot are female. I was hoping it was Larry, but at the same time was also hoping not. I had never meet him, just heard about him.
Again the room went silent. I know it was at least a half hour before they came back in. I had to go take a shit really bad. All that liquid up my asshole was very hard to keep in. If just I relaxed a little I knew it would all come out. My nipples hurt from the clamps that had been put on me some two hours ago I guessed. My chest and stomach hurt from lying on the table. I was in misery and just wanted to go home. Linda had tortured me before but it was constant attention which did not allow time to think of pain of misery.
I was released from the table and then the tube was removed from my ass. I was taken to the toilet and told I could go. I started going even before I was completely seated. I sat on some of the ass juices that hit the seat, but I really could not have cared at this point. I was cleaned and taken up stairs. My ankle and wrist bands would be removed as long as I agreed to be a good boy. I agreed and they were removed. I was laid down on the bed with the blind fold still on. The clamps were removed from my nipple and Linda apologized for them she had forgotten they were on. I was no longer in pain but not really excited either. Linda then laid on top of me and I put my arms around her. She told me that I could go and suffer some more or I could go home or I could get ready for the time of my life.
I agreed to stay out of curiosity mostly. I asked who her friend was and she told me I would have to wait. She then began kissing me. Moving her lips all over mine. Licking my lips and ears. She then gave me one of the longest most passionate kisses of our relationship. After we finally broke the lip-lock she move down to my chest, she teased my very sore nipples with her teeth and tongue. Then there was another mouth on my nipples, Linda was on one and another mouth on the other. I just knew it had to be a male. My cock was now rock hard again. I could feel the roughness of a five o'clock shadow. I was sure that it was a male and that I was going to be fucked up the ass by him. They slowly teased my nipples and played with my balls and cock. Linda stayed on my nipples and the other moved down to my cock. I was licked up and down the shaft, my balls were licked and sucked. My newly shaved ass was then licked. My legs were moved up to give my asslicker more access to my hole. Linda asked if I was enjoying all the attention, when I said yes, she told me that the best part was just about to begin. She then mounted me so that her cunt was right over my mouth. Without a word I began to suck and lick her juices. My legs were spread apart and lifted more toward my chest. Each leg was then placed under Linda's arms. My asslicker then move up behind me and I felt his cock for the very first time as it was placed at my hole. I could not speak because my mouth was full of cunt. I felt his cock begin to spread my hole open and move inside me. What pleasure. No pain this time. It slid in a little at a time going deeper each time he pulled back and move in again. I soon felt his balls against my ass. Yet he was still going in deeper with each plunge. It felt great. Soon he was moving in and out of my ass with ease. I was begging for him to fuck me and fuck me harder. As I sucked every juice out of Linda, I felt her cum. Almost as soon as she came I came without even touching my cock. My male fucker was still going strong on my ass when Linda got off of me and removed the blind fold. I was very shocked. It was Kevin. He is the QB for our football team and the one's ass I kick the day Linda came over. I found out that Linda arrange the fight that day telling Kevin that I was fucking her up the ass, something the he had always wanted to do but she would not let him because of the size of his cock. I watched as his cock slid in and out of my ass. It was huge, how did he ever get that thing in there without it hurting. I reached my arms up to him pulling him close to me and asked if he liked my ass better than Linda's, he just smiled and as I kissed him with a deep kiss he came in my ass. It was great, the feel of his hot spew in my ass as I kissed him.
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