Sam 03

You should really read Sam part 2 before reading this.

After Sam's tale of betrayal and non-consensual drugged sex, I was more certain that I wanted to marry her. I asked her to marry me on Thanksgiving and we spent the Christmas break visiting each other's families. Our plan was to marry in June or July, and we had both agreed to a small wedding which made neither of our families happy. We ended up on a compromise with a small ceremony in a chapel and our parents could do what they wanted with the reception. Both our moms went to work like they were planning the D-day invasion.

Sam was always apologetic about not telling me earlier about the event at the frat house. I am not sure if there is a "best time" to tell your significant other about such a tragedy. The frat house event did not bother me, but some of Sam's other sexual adventures made me a little uneasy. To make matters more complicated, Sam decided that we should both me more open about our past sex lives to ensure there were no more secrets. My sex life took about 15 minutes. Although, I had about a dozen lovers, there was never anything kinky and none of those relationships lasted very long.

Sam's stories usually came after sex when we were high on pot. Maybe something triggered a memory during our lust. Those stories would frequently end up with the two of us fucking again. Since the stories were disjointed and we were high, I had trouble putting Sam's sex life in order. I'm not sure why it troubled me, maybe because I'm a mathematician and things need to flow, and they didn't.

I reviewed some basic facts:

First, Sam did not attempt to have sex until prom night a few months after she turned 18. Neither she nor her lover knew what they were doing, and the sex was horrible. Fearing that it was her fault, she was afraid to have sex again.

Second, based on advice from her mother, she began looking for someone older and began an affair with a record store owner, Jackson. He was at least ten years older than she was and the affair began in June and ended in August went she left for college.

Third, Sam had a normal sex life during her first semester at college. Normal for a girl away from home the first time. She dated several who she had sex with, most of which were one-night stands. She certainly had a lot more lovers than I did.

Fourth, she actually met Cheryl (her nemesis from the frat house incident) during the spring semester of her freshman year and not in her sophomore year as I had thought. They did not become roommates until her sophomore year, but they started a sexual relationship in their freshman year. Cheryl was not the only woman Sam had slept with. I sometimes fantasized about watching Sam with another woman.

At times, I worried that Sam was really a lesbian and would leave me for another woman. Other times I worried that she had probably been with better lovers than me and would eventually grow dissatisfied with my skills.

The missing piece in the flow was what happened between high school and college when she was having the affair with Jackson, the record store owner. The things she did with Jackson were hard to comprehend.

I am going to try and summarize what Sam told me about that summer into one coherent story. Tales of her relationship were told over many nights after smoking some pot. So, the best I can recollect, she told me the following:

"During high school, I was discovering music and the math in music. My friends and I would spend a lot of time in the local record store. I took notice of the guy who owned and ran the store, and I began spending some free time helping him out in the store. Jackson was about ten years older than me. I also noticed that a lot of other girls and women would come in and flirt with him and I would see them leave his apartment over the store the next morning. Jackson had many lovers; old and young, white and black. So, I decided to shed my baggy clothes and wore make-up for the first time. Jackson noticed right away."

"One night after closing up the store, Jackson invited me to come over to his place and listen to some music. Here was my chance to have sex with someone who knew what he was doing, and I froze. Then I started blabbering and then I was crying. I had this vision that this really cool guy was going to try to have sex with me, and it would be a disaster like last time. Jackson was dismayed, and kept saying it was okay, he'll just give me a ride home."

"In between sobs, I found the courage to tell him why I was crying. He listened with a polite smile on his face while handing me a box of Kleenex. Jackson took my hands and said, 'look, you never have to do anything with me that you don't want, but if you want to learn about sex, do what guys do and watch porn.' Jackson went into his office and came out with some DVDs and a couple of joints. He told me to smoke a joint first and then watch a DVD."

"That night I did what he suggested. I never smoked pot before and after only a few puffs I was very high. I put in the first DVD which put me off at first, but then I felt myself becoming aroused. The pot was definitely making me relaxed, and I could feel how wet I was getting. Soon my hand found its way into my panties, and I had my first orgasm."

"I went back to the record store a few days later to return the DVDs and hopefully get some more pot. Jackson gave some new DVDs and some joints. He also offered to give me a ride home after he closed the store that night. As soon as he started the car, he lit a joint and handed it to me. I had a skirt on and when Jackson wasn't smoking the joint, he was resting his hand on my leg. Some of the DVDs I watched had interracial sex and I never thought about it until I saw his black hand on my very white thigh. After every hit of the joint, he would put his hand back a little higher on my thigh, pushing my skirt higher and higher each time until my panties were on display. I spread my legs to give access to my panty covered pussy.'

"Jackson pulled into my driveway and after parking the car, he leaned in and started kissing me. Soon his hand found my breast and he began playing with my nipple. I let out a moan and he asked me if I liked that. I told him I did and asked him not to stop. Jackson sat back in his seat and said, 'show me.'"

"I didn't know what he meant and then he said, 'Take off your panties.' I readily took them off. Jackson told me to spread my legs and play with my cunt. I told him I was too embarrassed to play with my pussy in front of someone."

"Jackson said, 'we both know you have spent the last few days masturbating like a mad woman. Why hide it, be comfortable with who you are. And it is a cunt not a pussy, a pussy is a cat. Now start rubbing your clit.' I did as I was told slowly at first, but the mixture of the pot and the exhibitionism were having an effect on me. Soon, I had two fingers working in and out of my cunt."

I didn't know Sam had a thing for exhibitionism. It never came up before in our sex life. I like watching women masturbate so, with a little prodding, Sam masturbating for me became part of our sex life.

"While I played with myself, Jackson unbuttoned my blouse and pulled it open. His black hands began to caress my bra covered breasts. I closed my eyes and leaned back moaning enjoying the sensation. He asked, 'do you like watching my black hands playing with your tits?' I moaned yes and he said, 'then open your eyes and watch.' I did as I was told. I watched him unclasp my bra and begin playing with my naked breasts. I was about to come, when he pulled my fingers out of my cunt and told me to taste myself. At any other time, I think I would have been mortified by the idea, but I began to lick my juices off my fingers. As I was enjoying my taste, I felt his finger start to work into my cunt. Jackson kept saying how tight I was. He also started to rub my clit with his thumb. I had the most powerful orgasm of my young life."

"After I calmed down, Jackson pushed his middle finger into my mouth and told me to suck it clean. I did as I was told. The he told me to pretend it was a big black cock I was sucking. Again, I did as I was told but I did not really know how to suck a cock. I had seen women sucking cock in movies, but I never focused on what they were doing. After a few minutes of stumbling around, I pulled his hand from my mouth and told him I did not know what I was doing. He told me to see him in the morning and said good night."

"I went into my room and lit up a joint. One of the movies he gave me featured interracial sex. I think I came five times watching the movie. I tried to imitate the blowjobs using the handle of my hairbrush."

"When I went to see him the next morning, he handed me a small tote bag. Inside were a couple of dildoes, a but plug and an instructional video on how to suck cock. He told me to send him pictures of me fucking the dildoes and other toys. He also offered me a job starting the following Monday."

"I went home, lit a joint, and did as I was told. The dildoes were much bigger than my old boyfriend, but with the pot and the porno, I was eventually able to work it all the way in. Taking a picture with my phone was difficult but I managed to do it. I sent him the picture and he called back right away using Facetime. He wanted to watch me fuck myself with the dildo. I did as I was told and soon had a mind-blowing orgasm."

Somewhere in here I started asking Sam questions about what she was thinking. Trying to explore sex was understandable but sending Jackson pictures was very risky. Sam said she had an eight-week window between the night in her driveway with Jackson and when she had to leave for college. She said she wanted to make the most of it since it would be horrifying the have a repeat of her prom night with a college student. She was not thinking about risks but whether she would ever have intercourse with Jackson since he seemed more interested in watching her masturbate. Sam said she certainly learned to enjoy masturbating, especially when someone was watching her. Sam continued:

"Jackson called me the following morning and asked if I liked the butt plug. I had to admit that I could not get it in, so he told me to come into the store right away. He locked the door to the store after I walked in and led me upstairs to his apartment. I had on a skirt and some regular panties. Jackson told me to lean over the back of his couch and pulled down my panties. I never felt so exposed in my life. Jackson was trying to work the plug in with some Vaseline, but I could feel my butt clench every time he tried to push it in. I was stunned by three sharp slaps on my ass and then the plug slipped in. He worked it in and out a few times while he reached around and grabbed my clit, and I came."

"I continued to masturbate for him which now included slipping a dildo into my ass while watching DVDs featuring anal sex. The next time he touched me was after my first day of work when he invited me up to his apartment. I thought he was finally going to fuck me, but he had different plans. He recorded a masturbation session with a small handheld camera, directing it like a movie, telling me to insert different dildoes into my cunt and then licking them. Throughout the session, he was calling me his little slut and I was calling him daddy."

"After I came, he stood over me and told me to suck him off. I had been watching the instructional video he gave me and practicing on the dildoes, so I was confident I knew what I was doing. At one point he grabbed my hair and began working his cock into my throat. I had also practiced this with the dildoes, but I had more control then. After he had my nose pressed against his belly, he began fucking my face while filming it with the camera on a tripod. It was not long before he was coming down my throat. I pushed him away because I wanted to taste a man's come and I felt and tasted his come on my tongue and then he pulled out completely and sprayed my face. With the camera focused on my face, he directed me to 'gather daddy's come with my fingers and lick them clean.' Of course, I did as I was told."

This part of her story led to an intense night of sex between us. There was an eight-hour ride between her parents and mine and on one of those trips, we stopped at an adult store and Sam purchased several dildos and but plugs. We had a lot of fun with the toys, and I loved shoving my cock into her mouth while she worked a dildo in and out of ass or pussy.

We also discussed how much she enjoyed being on camera and the role play of calling Jackson "daddy." Sam said all of this was so new and exciting that it was hard to tell what really turned her on. She had seen the 'daddy" bit in a number of the porno films she had watched so it just seemed natural to fall into that role.

"Jackson wanted me to dress sexier in the store because he thought it would be good for business. He had a "friend" taker me shopping to pick out some short skirts and crop tops. Jackson didn't want me to wear a bra or panties either, so my nipples were always on display. I found the revealing outfits very exciting. In high school, I hated the way men stared at her, now I loved the idea that they might go home and jerk off thinking about my short skirt."

"The short skirts gave Jackson easy access to my pussy and ass, and he would frequently slide a finger up my slit when I was working. Jackson's friends noticed his behavior and soon they were also feeling me up in the store. They also liked to lift my skirt and take a look and my naked ass or cunt."

"My next few nights with Jackson were more of the same with different dildoes including a double one I was able to work into my ass and cunt at the same time. Each of those sessions were recorded and ended with him coming in my mouth. I told him I wanted to fuck, I wanted to feel his cock inside me. Jackson said I was not ready yet and handed me a larger dildo with a suction cup on the bottom. He told me I was to stick it on the floor and practice going up and down on it."

"I did that a few nights with Jackson watching me, on facetime or in his apartment. If we were in his apartment, he had his camera out recording the session. Jackson showed me that I could also stick it on a wall and either back my cunt onto it or suck on it while on my hands and knees. Finally, Jackson told me I was ready."

"After work, Jackson led me up to his apartment. He had two cameras set up on tripods and a handheld camera. After sharing a joint, he told me to strip slowly and to lay back on the bed with my ass on the edge. Jackson brought the camera up for a closeup of my pussy which I had been shaving since I met him. I knew I was dripping wet. Jackson told me to grab my knees and spread my legs.

"Jackson asked if I was his little slut while the camera was focused on my face. I told him I was his slut and I wanted him to fuck my tight white pussy with his big black cock. I watched him begin to slide his cock into me, watching each inch disappear, telling him how much I loved daddy's cock inside my cunt. Soon he was all the way in, and he began to really fuck me. This is what I wanted, especially after watching all the porn movies I had seen. We switched positions a few times and then I felt him coming and I had a powerful orgasm too. Finally, I felt a man come inside me."

"Unfortunately, we only had a few more opportunities to have sex before I left for school. On one of those occasions, Jackson fucked my ass. I was surprised at how much I enjoyed it. I do not know why, but I was always horny and wanted more. Jackson was always busy with his other lady friends. He told me that his lady friends actually paid the rent, and the store would not survive without them. So, he told me to fuck his friends. Most of them had already had their hands under my skirt. Jackson set up a night where one of his friends helped us close. I had my first three way that night. Jackson recorded some of those sessions too."

"Jackson gave me a gift-wrapped box on my last day and told me to wait until I got home to open it. I unwrapped it as soon as I entered my room. It was a nice wooden box that opened with a key which I found after sorting through the wrapping paper littering the floor. Inside the box were DVD's containing all our sessions together. There was a note that said they were the only copies and he hoped I enjoyed them if I got lonely at school."

Of course, I asked her where the box was. Sam said it was hidden in her bedroom at her parents' house. Sam grabbed my cock and whispered in my ear if I wanted to watch his future wife masturbate and fuck other men. It did not take long for me to come all over her hand which answered her question.

But I did not want to watch Sam fuck other men, ever. The stories were erotic and stimulating but the possibility of seeing it troubled me. I was also troubled by Sam's behaviors. Certainly, she could not be held accountable for what happened at the frat house, but she told me she had sex with multiple partners while she was with Jackson. Or was I just being a prude because I would not have said no to having sex with two women at the same time.