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My Biini Summer

My Biini Summer

by Libertine2317
20 min read
4.68 (13100 views)
analoral sexbdsmfirst timeanal sex
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It was the summer after high school graduation, life was about playing and the real world of college or a job was something we didn't worry about. It was 1976 in Los Angeles. I spent most of my time up at my friend's Tony's house, well, it was his parent's house but they travelled a lot in the summer so we had the place to ourselves. It was up in the hills over Hollywood and had a pool, the view from the backyard looked out over the city and the smog.

Tony was a muscular guy; he played football and was in good shape. His skin was dark and his hair was black and he was very handsome. I was slim and lightly tanned and my hair was bright blond, bleached by the sun. We spent high school partying and going to the beach and getting high and still managed to graduate with decent grades.

That summer I pretty much lived up at Tony's, sleeping on his couch and swimming every day. His parents had a video tape player, a VCR, and we watched movies at night. I used to watch him swim and lie out in the sun and felt conflicting urges; I didn't understand my own feelings then. I knew he was watching me too, I'd lay out on a towel and rub baby oil on my skin so I'd tan darker and his eyes roamed over my body.

One night he brought out a cardboard box full of video tapes and grinned at me.

"I found this in my father's closet."

He rummaged in the box and pulled out a cassette, it had a plain label with a hand written note that said just said 'by the pool'. I watched as he slid it into the VCR and pushed play. We sat on the couch and I saw the first porno in my life. It had terrible sound and terrible acting but I saw real hard core sex for the first time. I watched as the woman knelt in front of the man and took his cock into her mouth and sucked him until he came in her mouth and all over her face. I couldn't look away.

The couple on the screen fucked in more ways than I knew of. We watched that tape and others, glancing at each other from time to time, as men and woman writhed together and moaned in ecstasy. When it was late we shut off the TV and VCR and Tony went to his room. I sat there with a hardon and finally went to the bathroom and masturbated in front of the mirror, my hand slick with lotion, watching myself as I stroked my cock until I finally came into the sink. I didn't sleep much that night.

The next day we swam in the morning, finally taking a break and making lunch, then sat down to watch more of the porn tapes. Tony pulled out one that simply said 'two guys' on the label, written in pencil. We looked at each other and then I put the tape in the machine and pressed play.

We watched as two young men, older than we were by a few years, did things we'd never imagined. They lay together and sucked each other's cocks, 69 style. One of them spanked the other with a hair brush and then put Vaseline on the handle and slid it into the other's asshole. We were barely breathing. Finally one of them bent over the arm of a couch and the other one fucked him. It started with slow, languorous strokes as we watched that hard cock pump in and out of his ass, then the action became harder, faster, the one on top pounding his cock up the other's ass as deep as he could. At the end he pulled out and stroked his own shaft until his cum sprayed on the ass and back of the one on the bottom. The tape ended.

We didn't look at each other; we just stared out the window behind the TV. I took a drink from the can of beer on the table and tried to make up my mind. Finally I decided.

I slid off the couch and knelt between Tony's legs, looking into his dark brown eyes. I hooked my fingers in the waistband of his swimming trunks and pulled them down; he had to lift his ass off the couch so I could them off. He was hard, a pearl of precum already on the tip. I wrapped my hand around his rigid flesh and squeezed, making him moan softly, then I copied what I'd seen a girl on the tape do and licked the crown of his shaft, making him gasp.

I opened my mouth wide and filled my mouth with his cock. He sat there unmoving, watching me as I clamped my lips tight around his cock, sucking hard. I had watched the tapes yesterday and started bobbing my head up and down slowly. I'd never done this before but it seemed like the most natural thing to do. He moans and squirmed a bit and I wrapped my fingers around the base of his cock and started stroking, like I'd seen a woman do on a tape the day before. I sucked him harder, my tongue pressed up along the underside of his penis, squeezing and stroking him with my hand. He didn't last long, suddenly his hips moved and he was trying to push more of his length past my lips, then I tasted his cum for the first time as it flooded my mouth. I gulped and swallowed as much as I could while some ran from the corners of my mouth.

I realized that I loved having his cock in my mouth, in that one moment I discovered a truth about myself. I knelt in front of him and savored the aftertaste of his seed as he lay back and closed his eyes. We didn't speak; we didn't know what to say. Finally I got up and went outside and dove into the pool.

I swam laps for a while and then got out, standing there looking out at the city thinking about what had happened. Then I stripped off my swimsuit and lay out on a towel under the sun. I heard the sliding door open but kept my eyes closed, enjoying the heat on my skin. I knew he was standing over me, looking at my bare body and trying to decide what to do.

After a long moment he sat down on the towel next to me and I heard the pop of the baby oil bottle open. He started to rub the oil into my skin, his strong hands kneading my muscles, coating my back until it was shiny, then he moved to my legs, stroking them as I relaxed under the hot sun. I think I fell asleep there for a moment, lost in the sensations, until I felt his hands on my ass.

His fingers dug into my ass, working the muscles and getting my skin all slippery with the oil. I moaned softly but didn't say anything. Then I felt him spread my cheeks apart to expose the cleft of my ass. I think he stared at my asshole for a long moment; then I felt his finger tip rubbing that right ring of muscle. I spread my legs more and lifted my hips up, encouraging him. I felt him press one slippery finger into my ass, it hurt a bit, he was clumsy. It felt odd, this unaccustomed intrusion, but it was exciting. He started fingering my ass, sliding in and pulling out. I got hard and soon was leaking onto the towel under me. Tony poured oil along the crack of my ass and worked more into me. It hurt still but also felt good, I was moaning softly, I didn't want him to stop. I knew what was about to happen and wanted it to happen.

Suddenly he slipped his finger out of me, and I heard him taking off his shorts. I licked my lips and shivered slightly, anticipating what was to come next. He straddled my thighs and I felt his hard cock rubbing along my slippery skin, then he set the tip to my asshole and started to push into me. I tried to relax, taking deep breaths, and he had to push harder, struggling to get into me. He stopped, changed his angle, and tried again. It started to hurt more, I could hear his breathing, his hands gripped my ass and spread it open wider; he pushed harder. Suddenly he popped through and had the head of his cock in my ass. I yelped and closed my eyes, the pain was intense for a moment; a burning sensation as the ring of muscle was forced to stretch open wider than it was used to.

Luckily Tony wasn't some huge stud, his 6 inch shaft started to slide into me as I bit down on a fold of the towel and whimpered. He kept moving, his hips shifting, as he worked his cock into me.

"Stop...wait...give me a minute," I whispered.

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"Sure, yeah, it's cool."

He waited, about two inches of his cock in my ass, as I tried to relax, taking deep breaths. He was patient, not moving, as I started to get used to this.

"OK, yeah, more."

He moved again, pushing more of his length up my ass, slowly, taking his time despite how good it must have felt with my tight flesh squeezing him. I squeaked and moaned and winced as his cock went into me, then I felt his hips against my ass. I had taken it all.

He lay out full length on me, his weight pressing me down, and started to roll his hips. I felt his cock sliding in and out of me and began to moan, it felt good even though it still hurt. He began to fuck me steadily now, grunting as his hip hit my ass and his cock speared deep up my ass. I was leaking precum as I was held down and used.

I was making noises; squeaks and whines and grunts as he fucked my virgin ass. I clawed at the towel under me and drooled down my chin as I felt his cock moving in me, helpless under his weight.

Tony fucked me faster, gasping, he pounded his cock into me frantically, this was so new to him that it was over quickly, he cried out as I felt a cock pulsing inside me for the first time. His orgasm was intense, I could tell, every muscle was tense as he groaned, shoving his cock into me again and again, then he lay still on top of me, keeping me pinned down and impaled. His breath was warm on my ear and then he kissed the back of my neck.

Eventually he rolled off me and got up to dive into the pool. I lay there discovering how I felt. My asshole was sore and I had a feeling that would last a while. My cock was still hard and I ached for release. I rolled over and poured some oil on my hand and masturbated under the sun, biting my lip, until I sprayed cum all over my belly in an intense rush of lust. Tony watched me intently.

We swam for a while, not saying anything. We didn't know what to say. What we'd done was forbidden, no one would understand.

That night I drove home and slept in my own bed. Before I drifted off to sleep I had an idea that left me smiling.

I was still sore in the morning and stood up at the counter in the kitchen to eat breakfast. I couldn't get the images of the day before out of my head and I masturbated in the bathroom until I came in the sink. After my mother left to go shopping I put my idea into action.

I went to my sister's room and closed the door. She was away for the summer and I was free to search for what I wanted. Jeanie was older and curvy and I found some bikini bottoms that fit me more or less. I rummaged around her makeup table and looked at one of her fashion magazines and put on makeup for the first time in my life. It didn't go well. I washed it off and tried again. And again.

I managed to get it right finally. Some blush on my cheeks and a bit of lipstick. I wasn't going to try eye makeup yet. As I looked in the mirror I was glad I didn't have to shave yet, my cheeks were smooth. I looked girly.

No one was home so I wandered around wearing bright orange bikini bottoms and makeup. I didn't like how my pubic hair stuck out of the edges of the bikini so I took a shower and then shaved my crotch smooth. I liked how it felt and how it looked as I gazed at myself in a full length mirror. After looking at myself for a while I went and shaved off the little hair that grew on my legs and then rubbed lotion on my skin.

I packed a bag and looked at the bikini bottoms for a while, I couldn't wear the top, Jeanie had big enough boobs that it wouldn't fit, so I found an old faded red t-shirt and cut off the body to just below my ribs, leaving my midriff bare. I took another t-shirt, purple this time, and cut it short as well as cutting off the sleeves. My makeup supplies went in next.

I was nervous as I drove up the hill to Tony's place. I almost turned around and went home. Eventually, though, I was at his door. It was late afternoon and he was doing laps in the pool so I used my key and let myself in quietly and went to the bathroom to change and put on makeup. When I was done I looked at myself in the mirror and smiled. I didn't look like a girl, but I didn't look like a boy either. The orange bikini bottoms fit me well enough and the cut off t-shirt was cute. My lips glistened and my cheeks were lightly pink. I'd put my hair into loose pigtails that hung down below my shoulders. I was ready.

Tony was laying on a chaise lounge by the pool when I walked out and said hello. He was used to me turning up at odd times and wasn't surprised: then he did a double take when he actually saw me. I waved and went to the railing to look out over the city, bending forward to show off my ass a bit, then turned around and smiled at him. He stared at me.

"Hi, Tony."

"Hey...ummmm..."

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I sat on the edge of the lounge and put my hand on his thigh, smiling at him, and then bent over to kiss him on the lips lightly.

"I know this is weird, Tony, so let's not talk about it. Just let it happen."

I bent down to kiss him harder this time, my tongue slipping past his lips. He didn't respond for a moment and my heart almost stopped, then he wrapped his arms around me and kissed me passionately. We rolled off the chaise lounge and made out like the frenzied teenagers we were. He licked and kissed my neck and groped my ass as I whispered to him.

"Call me Cassie. I want to be your girlfriend."

We caressed and touched each other until I managed to get his trunks off, then I slithered down between his legs and licked his hard cock from root to crown, slow laps of my tongue pressed flat to his hard flesh. He had one hand on my head as his hips rose, offering me his sex. I took it into my mouth and sucked him hungrily, slurping as my lips slid up and down his shaft, sucking hard and moaning with my mouth full.

He moaned loudly as I sucked his cock, his hips moving, then his hand pushed my face down as he thrust his cock past my lips, fucking my mouth, using me instinctively, I sucked and gagged and drooled as he pumped that hard shaft into my mouth, my lips clamped tight around his flesh. He didn't last long.

He grunted and I got my reward, a mouthful of cum. I kept sucking him as he filled my mouth, then he grabbed my hair and yanked my head up so his cum sprayed across my face like that girl in the movie. After his release he lay back and sighed and I did the most natural thing in the world, as far as I was concerned, and licked his cock clean.

He sat there smoking a joint and looking at me with a lazy smile. I pulled my bikini bottoms off, took a jar of Vaseline out of my bag and smeared some on my fingers, then knelt facing away from him so he could watch my greasy fingers sliding into my ass, stretching and lubing myself. I used one finger at first, then two, looking back over my shoulder to see his reaction as I got ready for him. Once I was loose and lubed I turned to him and griped his cock, squeezing and stroking him as he began to harden. Soon he was ready, his shaft standing up straight and all slippery with the lube; then I got on my hands and knees and wiggled my ass. I felt his hands grip my hips and the crown of his cock pressing against my asshole; then he was in me and moving. I had just sucked him off and he lasted a long time, fucking me by the side of the pool with the sun beating down on us as I moaned and whimpered and pushed back to meet his hard thrusts so he went as deep up my ass as possible with every thrust. He came in me for the second time and then watched me stroke my cock again and cum all over my belly as I lay there next to him.

This began our summer together. I stayed with him most of each week as Cassie, his girlfriend. I wore my bikini bottoms and crop top t-shirt or a scarf tied around my chest all the time. I learned to curl my long hair using things I found in Tony's mother's bathroom. I learned more about makeup, too, making myself prettier for him, and soon I was wearing eye makeup every day.

We never spoke much about what was happening; there were no introspective talks, but we did learn each other's bodies. He learned how to prepare my ass for his cock, slowly working me open with two and then three fingers coated with Vaseline. I learned how to tense up my inner muscles and squeeze his cock while he fucked me.

He called me Cassie and made me smile.

There were limits. He didn't want to touch my cock; I had to stroke myself to get off after he fucked me. He wouldn't let me play with his ass. Still, we were happy.

I found a baby doll nightie in my sisters drawers, buried under mundane underwear, during one of my visits home, and took it with me. It came down to just below my hips. I wore it all the time for weeks and he would push me down on the couch and fuck me hard. I was still a little sore after he plowed my ass but it was worth it every time.

We slept together in his parent's king sized bed like a couple and fucked like bunnies.

We were halfway through the summer when we turned a corner in our relationship. He was watching a baseball game while I knelt in front of him and licked his balls and cock, mostly teasing him. I never let him cum, taking him up slowly and then letting him back down. He grinned as he watched me serve him.

When the game was over he started the VCR. This was a tape I hadn't seen before, but it seems Tony had. I watched as a man used straps to bind a woman to a bench, then he began to spank her. He turned her ass bright red as she moaned and writhed. He pulled her hair and fucked her mouth as she was held helpless on the bench. He took a belt and whipped her thighs as she cried and moaned. My mouth was dry and my heart was racing. Somehow I knew what was about to happen next.

Tony stood up and took my hand, leading me out by the pool. There was a picnic table there with benches just like in the movie. He kissed me and hugged me and undressed me, then led me to the bench and pressed me down on it, laying me on my stomach. He bound me with scarves he'd found in his mother's closet and picked up a wide belt. I was trembling and almost unable to take a breath.

The first kiss of the belt was across my ass; I jerked against my bonds but made no noise. The second and third followed and my ass was on fire, the stinging sensation spreading across my flesh. The fourth kiss of the belt was across the back of my thighs and I cried out. My cock was as hard as a bar of iron. He whipped me 5 more times as I cried and finally yelled and then he set down the belt. I was sobbing and gasping and so turned on.

After pouring a bit of oil on his cock he mounted me as I lay there tied to the bench. I moaned as I felt the crown of his cock spreading me open more and more until he was inside me. He hadn't prepared me at all and it hurt, but I was his girl and he could use me as he wished. I whimpered as his cock sawed in and out of my ass, stretching me and filling me. He was taking his time, fucking me slowly; he wasn't going to cum fast this time. He thrust into me deep and then pulled back all the way out, leaving me empty and mewling with disappointment, then thrust back through my loosened asshole until he was balls deep in me, only to pull all the way out and do it again.

He was relentless, fucking me like a whore, using me, and the pain and pleasure wove together in me as sensations I didn't understand filled me. My whole world narrowed down to his cock in my ass, pumping into me like a piston, never stopping, my head was spinning, my ass started to tighten. His pace increased, he was getting close now, I could tell, he was driving into my ass harder, faster. Suddenly I squealed, a thin and high pitched noise, as I came from just his cock in my ass. He had fucked me to an orgasm without me touching my cock. I squirmed and moaned as my asshole clenched down hard around his cock, then relaxed, then clenched again, my climax surging through me as I squirted on the towel he'd put over the bench. Each thrust of his cock up my ass made me squirt again as I moaned and whimpered.

He lost control then and reamed my ass hard, spanking me as he fucked me. I cried and howled and moaned as he hammered his cock up my ass frantically, the pressure in his balls driving him over the edge until he exploded in me, filling me with his seed, breeding me like the bitch I now was.

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