Fucked By My Boyfriend's Family by somebastard69

My boyfriend Jim knew I was sexually innocent when we first started dating. We met as teens at our Catholic high school and spent a couple years dating and teasing each other before things started really heating up. In the beginning of our relationship, I was content with kissing, necking, and heavy petting– never letting him touch my privates or see me naked. Never before had I even touched myself! Jim, though, was a typical horny guy — confessing to me that he looked at his dad’s porno movies and magazines almost daily and he masturbated to the thought of having sex with me. Jim coaxed me into opening up sexually as time went on, telling me his fantasies and what he longed to do to me, saying he wanted to give us a family and be with me forever. One day after school, we were at his place on the couch when he started rubbing my crotch through my white cotton panties. His sudden touch surprised me at first, but began making my juices start flowing. We locked eyes in a heated gaze.

“What are you doing, Jim?” I asked.

“I’m rubbing your pussy, Elizabeth. Tryin’ to make you feel good…” he said to me, cupping my pubic mound in his hand. “This is your pussy, it belongs to me.”

“My vagina?” I said, giggling.

“Your cunt. Your pussy. Your fuckhole. Come on Elizabeth, we’re not at church right now… You should allow yourself to be pleasured. You should tell me everything you can think of that could possibly bring you pleasure, and I will see what I can do,” Jim said as he continued rubbing my “pussy” through my white cotton panties. I smiled at him. He was making my panties wet, for sure! I could feel the viscous fluid making my sparse pubic hair moisten against the fabric.

“That feels good, definitely,” I replied.

“I can do so much more, Lizzy… Why don’t you let me?”

“Well, I don’t know, I don’t think I’m ready to go too far…”

“What, you don’t trust me?” Jim asked, looking somewhat hurt. I looked back at him, smiled, and spread my legs open a little wider for him. He continued rubbing along my moistened slit through my panties. Suddenly I felt his finger slip inside my panties, making me jump a little. I was still wearing my uniform– plaid skirt, white knee high socks, white buttoned up shirt, and my navy blue tie. He began kissing me as he rubbed my pubic mound and up and down my slit, slipping his fingers in and out of my panties to feel my moistened sex. I kissed him back, feeling his manhood bulging in his pants, pressing against my belly. He still had his uniform on, too.

He took his other hand and began rubbing my small, budding breasts with it as he kissed me. His efforts did feel good, I can’t deny it! Then, to my surprise, he took one of my hands and placed it on the bulge in his pants! On his hard penis! It felt like steel in his trousers. He smiled at me, asking me if I’d keep touching it. I gulped and nodded reluctantly — I didn’t know how to properly stimulate a penis!

Jim guided my hand all over his throbbing bulge, kissing my neck passionately as he continued fingering me. It was hot! I didn’t want to go any further, so I stopped him soon after. He was very frustrated, to say the least. I watched, shocked, when he unzipped his pants and proceeded to take his cock out anyway, even though I told him I didn’t want to do anything else! My eyes were wide as he stared back at me, his hard meat in his hand. He began jerking himself off steadily while locking eyes with me. I have to admit, it was pretty hot seeing a cock for the first time. The tip of it was all red and dripping pre-cum, veins bulging throughout it. He had a pretty good sized cock for a 16 yr old!

“Come on, Liz, let me cum on you,” Jim said through gritted teeth.

“What? Where?” I exclaimed.

“Let me cum on your pussy,” he said, breathlessly pumping his meat next to me on the couch. I was hesitant, but eventually laid back and hiked my skirt up a little. Jim stepped up in between my legs and continued pulling hard on his dick. His eyes were gazing hard into mine. I jumped as I felt him pull my panties to the side and press the head of his cock against my wet lips.

“Jim, what are you doing?” I said, confused and a little nervous.

He grunted, continuing to pump his cock as his cockhead was pressed right up against my wet slit. I moaned involuntarily as he rubbed his meat all up and down my pussy, from clitoris almost to asshole. His balls hung low and jiggled with his dick-pumping efforts. Never before had a penis touched my vagina! His rod was slick and hard, veins coursing throughout. It looked to be about 7″ or so.

His face contorted and he groaned loudly, his cock touching my clit as he pumped it over me. Suddenly I felt streams of liquid coating my slit, all up and down my gash! He was cumming on me! Jim continued grunting breathlessly, pumping his meat a few more times, rubbing his semen into my cuntlips with his hard cock. His prick was still touching my wet slit as he bent down and kissed me hard. Jim then pulled my panties back over my pussy mound, keeping his cum sealed up in my panties.

Eventually I let him go down on me, and he eagerly ate my pussy out while fingering me hard. I had never had an orgasm before, and Jim was determined to give me one. He started going down on me every night after school, making me crave his oral attentions throughout the whole school day. He finally succeeded in making me cum one evening while I was spread out on my bed, my parents in the other room. I had to put a pillow over my face to muffle my moans as he made my body writhe before him.

I decided to return the favor, and he taught me to give him head and praised me as an “excellent cocksucker” and “a natural, with perfect dick sucking lips!” We would sixty-nine each other, but I didn’t want to go any further than oral sex. Jim wanted to teach me the pleasures of sex, going on about the joys of vaginal and even anal sex! Apparently he had tried it a few times with another girl (that he was actually screwing the whole time we’d been dating, I later found out).

Jim was constantly trying to persuade me to have sex with him. He wanted my virginity, badly. I had wanted to save myself for marriage, but shortly before graduation I eventually gave in to Jim’s incessant begging for my cherry. It took place in his bedroom, with me laying quietly on my back as he rutted away on top of me, taking my innocence. I wasn’t on birth control, so he had to pull out and cum on my belly. The first few times weren’t very pleasurable– Jim didn’t last very long. He eventually got better the more we had sex, and I grew to enjoy it more, too!

I told him I didn’t want to have anal sex, and made myself very clear about it. A year or so after graduation, we were at his place drinking some of his dad’s alcohol and having a pretty good time when I guess I fell asleep. I must have been pretty tired that night, as I had only had a couple drinks. The last thing I remember is talking to Jim out on the couch as we drank.

When I awoke at some point later, I was in the bedroom, on my back on his bed! My eyes opened blearily, widening with surprise as I realized I was naked. Jim was on top of me, I suddenly realized, and his penis was inside me! It wasn’t in my pussy, either! He was fucking my ass!

I felt so groggy, so heavy, I couldn’t even move my limbs or speak. My eyes were teary, and they stared up at Jim’s, pleading for him to stop. He smiled down at me. After a few minutes I was able to squirm around on the bed, but Jim was stronger than me and kept pounding my ass as I lay folded up beneath him. The pain in my ass was like a searing iron surging into my guts. I began whimpering and moaning as I lay prone, weak and tired.

Jim gasped and I felt his cock pulsing in my chute, suddenly unloading his semen deep within my bowels. He was grunting as his cock pulsated within me. I stared up at him, shocked. After a few moments, his breathing getting calmer, he began pulling his cock from my ass. It felt like he was ripping my insides! I squealed while he pulled his member from my bowels, cum dripping from the head of his dick. He slapped my ass cheek with his prick after he pulled it out of me, leaving a trail of cum on my butt.

Later, after I had regained full consciousness, Jim and I had a long talk about him fucking my ass. He convinced me that I told him I wanted him to fuck me up the ass while we were drunk, and he was simply obliging with my wishes. It was dubious, but then again, I had been pretty intoxicated that night. So I forgave him — but I told him I didn’t want him fucking my ass again!

We had a pretty happy relationship, having sex fairly regularly through our college years together — I’d say at least 5 times a week. He got me to confess to some fantasies (like sex in the lecture hall at school), and told me some of his own — like his fantasy of me in a nurse uniform. Then he asked me if I’d ever thought about being tied up…

I was surprised. No, I’d never really considered it. Jim told me I should succumb to him, and let him have complete control over my pleasure. That I should trust him… I was hesitant, though I did love him and had never been with anyone else. The thought of me being bound to a big bed with silken ties while he had his way with me was kind of sexy…

One night we were drinking some of Jim’s dad’s cheap liquor back in Jim’s old bedroom, sitting on his four-poster bed as we talked and kissed. After we got pretty buzzed, he brought up the idea again of tying me up. Since my inhibitions were lowered and I was feeling frisky, I relented. Jim was thrilled. He went to his dresser and got two pairs of handcuffs and a velvet blindfold. My heart started beating fast — I’d never been restrained before while making love.

Jim stepped over to me and began kissing me all over as he laid me down. I was wearing a floral dress, a white lace bra and white matching panties, and nude pantyhose. He took the dress and bra off and kept my pantyhose and white panties on. He kissed my arms and small freckled B cup breasts, holding the handcuffs. With my arms stretched behind me, he began affixing me to the bed posts. I could feel the bulge in his pants rubbing against my thigh.