First Time Sex Stories Collections

First Time Sex Stories Collections

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Benefit of A Friend

I was born and raised in Brooklyn. It was my the beginning of my freshman year in high school that i met and started dating Robin, my high school sweetheart. We dated for three years and were crazy about each other. However, my dad's job forced me to move away the summer before my senior year to Vermont. Robin and I decided not to pursue a long distance relationship and decided to stay very close friends.
Well, Robin and I stayed in contact, oftenly talking on the phone for hours at a time. Although the "relationship" was over, we still had undeniable feelings for each other. About two months after I moved away I drove back to my hometown for the weekend. My parents decided to rent an apartment for me to stay at during college when I returned to NYC for school. When i got into town I called Robin. She only had one question, "When could you come over and hang out with me?

About twenty minutes later I pulled into her driveway. She was waiting for me on the front porch of her parents' brownstone in Bed Stuy Brooklyn. Before I got a "hello" out of my mouth she sprinted over to my truck and leaped into my arms, nearly knocking me to the ground. She told me she missed me more than i could ever imagine. I told her, "Well can we at least go inside, I'm starving..." once inside she threw a frozen pizza in the oven and told me it would be about ten minutes.
Well, twenty minutes and an entire pizza later i told her,"Thanks, I'm stuffed." So we moved to the living room and she flipped on the TV and started flipping around. She handed me the remote and told me she was gonna go jump in the shower and change and I could just find something on to watch. Well about forty five minutes later, she walked back down the stairs from her room to the living room. She had changed into her short denim skirt (a personal favorite of mine) and a small white tank top.
She strutted over to the couch and sat on my lap. She told me once again how much she missed me. I told her I missed her just as much. She leaned over my shoulder and wispered in my ear, "Friends with benefits?" She snickered as she saw the grin creep across my face. She told me that her parents were home, so we needed to find another place to "hang out." Well she ran down the hall to her parents room and told them we were heading out to a movie and she was staying at her friend, Britney's house.
As I walked her out to my truck I walked around and opened her door and helped her in (an old habit from dating her so long). However i noticed something was different this time. As she climbed form the side step of my cab into the seat, I caught a glimpse of the bottom of her ass, up her skirt. As i cranked the truck she called her friend Brittany and told her to cover for her and make sure her parents thought she was staying with her.
As we pulled up to my apartment complex Robin pulled up the middle armrest in my truck, slid over and whispered in my ear, "I know you love this skirt...and oh yeah, I'm not wearing any underwear." She must have known how crazy this drove me because she giggled. I turned to face her as I turned off my truck. For the first time in months I kissed her. I thought to myself,"Man i missed her!"
AS we ran up the stairs to my apartment on the second floor i caught another glimpse up her skirt, and she wasn't lying. She was panty-free.
As we entered my apartment, i turned to lock the door and as i turned back around she pinned me against the door. She smoothly, passionately french kissed me. In a common move of mine i slid my hands down her back to her ass. I then proceeded to lift her up as she wrapped her legs around my torso, continuing to make out with me.
I carried her like this back to my bedroom. She pulled away from me mouth and kissed down my neck and back up and laid one final kiss on my cheek and looked me in the eyes and said, "I want you to make love to me." although we dated for three years, she was a still virgin. Over the three years we had fooled around, including me sucking her tits quite oftenly.
I laid her on her back on the bed and pulled my shirt over my head as she sat up and pulled hers off as well. She laid back as i eased down onto the bed next to her. I slid my hand down her shoulder over her bra and stomach and brought it to rest on her inner thigh. She placed hers on top of it and slid it up her skirt. I moved my hand around to the back and squeezed her bare ass. She slwoly unzipped her skirt and slid it down and threw it off the bed. I manuvered up her back and unhooked her bra, revealing her beautiful 34D tits. During our sessions of fooling around i had eaten her out before, but this time she obviously wanted more. She told me, "I'm already wet, i just want you so bad right now". She rolled on top of me and un buttoned and unzipped my pants. She rolled off just long enough for me to shed my jeans.
She slid down and took my 10 inch cock in her hand and slowly licked up and down the side of my shaft. She proceeded to work the head of my member. She began bobbing her head up and down along my cock faster and faster. As she worked my dick with her mouth and left hand she fondled my balls with her right.
About five or ten minutes later i asked her, "Do you want me inside you now?"
All she could do was grin as she moved to the edge of the bed, where i then slid between her legs and told her i loved her as she took my shaft in her hand and guided me into her tight, virgin pussy. I couldn't believe how amazing her tight warm pussy felt around me.
I slid my hand up her stomach to her breast and fondled her nipple as i began pumping slowly. She began rotating her hips in rhythm with my thrusts. A few minutes later, she told me, "Okay its all your's..." I looked into her eyes and all my fellings for her strongly resurfaced. I began speeding up my pumps. Her moans grew more and more intense. She bit her lip and squeezed her tits, playing with her nipples. She looked up and said, "My turn..." as she grabbed my hips and rolled over, putting herself on top. Although my thrusts paused momentarily she let out a deep, laud, sensual moan. She brushed her brown hair back around her shoulders, giving me a perfect view of her amzing chest.

She began lifting herself up and down, pumping my cock in and out of her tight twat. Just then she stopped lifting and just grinded her hips back and forth. Well i felt climax draw near, so i told Robin, "I about to cum, where do you want it. She rolled off of me and said, "All over my tits..." i stradled her torso and she reached up and began pumping my cock with both hands. Moments later i felt my head swell in her hand and i unleashed my load all over her beautiful tits. As i finished cumming she leaned up and slowly licked the remaining cum from the head of my member and wiped the cum off of her chest and licked it off her fingers.
As she walked out of the room she hollered, "I'm gonna jump in the shower."
I threw on a pair of gym shorts as i heard the shower come to life. I brought her a clean towel from my laundry room and she giggled as she noticed me staring at her bare ass as she bathed. She looked over her shoulder and said sensually, "I have a surprise for you." I walked out into the living room and plopped onto the couch. She came waltzing down the hall in her towel. She was carrying her purse though. I could tell she had planned on this being a special night as she pulled some lube out and tossed it onto the couch next to me and said, "so you like my ass huh?"
She dropped the towel and walked around in front of me and said, "Bend me over big boy." I stood up as my erection reemerged. She opened the lube and applied it to my throbbing dick. She walked over to the recliner and said,"I'm ready," as she bent over.
I walked over and grabbed two handfuls of her amazing behind. Then i spread her cheeks and slowly drove my cock into her ass. She moaned in pleasure. I pumped slowly in and out of her tight ass. She moaned faster and faster. She told me i could go harder. I thrusted harder and harder and she kept moaning. I leaned forward as i pumped and cupped her breasts and said,"You want me to fuck you as hard as I can?" She moaned deeply, "Oh yes, oh yes..."
I kissed her on the shoulder and went to work. I pounded her hot ass as hard and as fast as i could, as she fingered her pussy. Her moaning grew very intense. She climaxed and her body shuddered. She looked over her shoulder and told me, "I'll finish you off baby."
She turned around and got to her knees. Again she gave me head, this time with more intensity. She bobbed her head up and down my dick furiously. This time she began deepthroating me. She took only 8 inches down and loved every second of it. I felt another climax approaching, and i informed her. She responded with a simple, "MMM-Hmm" with my dick in her mouth. I felt my member swell again and Robin deep throated me again. I released my load down her throat. She didn't even gag. "What an amazing girl..." i thought to myself.
Shw swallowed all of my cum and stood up with her smile beaming. I reached around her and picked her up by the ass again. I carried her down the hall and we fell onto the bed in one another's arms.
I awoke with her still in my arms. She woke shortly after i did. She leaned closer and i kissed her long and passionately. She smiled and said once again,
"Friends with benefits..."

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Loosing my Virginity

I was 18 when I had my first sexual intercourse with someone. Though I knew about sex from my friends, I had never got a chance to do it. I was all excited about doing it, but I never had a chance. And then my friend Lucy came to me one day. Lucy was from an ordinary middle class family, who used to study in my class. We became friends a year before. She always had enough money with her. I never asked her where she gets all those money from, but she

used to spend on things like crazy. My family never used to give me money like that. When I used to go with her for shopping, I always used to wonder where she is getting all these money from. She used to wear all sexy dresses and it matched her body structure. Though she was 16; she looked 18 and was huge. When we used to walk on the road, even college guys used to look at her. She was a charming beauty. Her boobs always bulged out of her tight dress. She used to discuss sex with me. I got amazed to know that she does sex with people. I never believed her until that day when she came to me with a proposal.
She told me about someone who pays her well for doing some small things that he wanted her to do. She asked me whether I am interested to join them. She said that I could make a lot of money simply doing simple things. I wanted to know more about the deal. She said that it was modeling that she is talking about in which I had to pose for some pictures. I really got excited with her talks. But I knew I was not busty like my friend, but I was cuter than Lucy. I had a ‘just above average’ frame compared to my friend. But Lucy told me that it won’t be a problem as long as my beauty is concerned.
So, one day I went to meet Mr. Steve who according to Lucy was the coordinator of the modeling program. Steve was a nice, cool chap, about 26 years old. He was a very charming guy and any girl would love him at first sight. He was clean shaved with a good physique and was wearing a t-shirt, jeans and a cap. He looked stunning. Lucy told him that I am interested in modeling. He called me inside another room. I sat there with him alone. He asked me some general questions. He seemed interested in me. When he said that I am beautiful, I couldn’t stop blushing.
The next day Lucy said that he is interested and he has called me in for a shooting session. I went the next day evening after my classes with Lucy to his studio. Lucy went inside the dressing room to get ready. In the mean time, Steve talked to me. But I got really shocked when I saw Lucy coming out totally nude. I could speak nothing. I stood there blunt. She said she was ready for the shooting. Steve called his camera man from another room. They took a lot of her nude pictures. To my further astonishment, Steve also got undressed. OOOhhh… he had a huge cock. They posed for many pics. They clicked some pics of them having sexual intercourse also. I didn’t know how she could do that. I felt so ashamed and I went out of the room and sat there.
When the shooting session was over, Steve gave Lucy a bundle of $100. I was shocked to see that much money together. I thought about the deal again and again that night. But the money was such a motivating factor, I agreed to do it. That was a turning point in my life.
The next week I was called in for a shooting session. Steve took care in taking my dress off. I felt embarrassed. He took my clothes so delicately, as if it may hurt me if he is rough. They clicked my pictures in bikinis, under wears, topless and totally nude. This was getting exciting. I loved this. That day we clicked about a 100 pictures. All solo pictures. He didn’t even touch me. I was given a bundle of $100 bills. I counted it and it was $1000. I was really shocked.
The next week when I got his call, I was totally excited. After the class, I ran to his studio. Again he undressed me and this time he also got undressed. Though I felt a bit awkward, I got in swing in no time. We started the photo session. We took pictures of me holding Steve’s huge cock, kissing it and putting it in my mouth. I was getting more and more excited. The shooting went good. But by the time it was over, I was so horny and wet. Steve realized what I wanted and called the cameraman again. He setup his cameras again. Lights were on. He kissed me on my lips. I closed my eyes. I forgot that I am in front of the camera. He sucked my lower lips and pushed his tongue into my mouth. I was enjoying this. He hugged me tightly and I was laying on him. In between the passionate kiss, I don’t know when he started to fondle my tits. I came to know that he is playing with my small tits only when he withdrew from the smooch. He raised my body and sucked my boobs. OOOhhh; that was a wonderful moment. I wished that moment to last for ever.
I was dripping wet by then. He laid me on the bed and started to suck my pussy. That was the first time a person other than me touching my pussy. I loved it a lot. He sucked it hard and his tongue intruded into my holes and he drank my juiced hungrily. I was reaching orgasm, and then he stopped what he was doing. Oh, that was a moment of desperation. He smooched me again and again. And then I felt his finger intruding my virgin pussy. He stuck his middle finger fully inside me and started fucking me with his finger. After some time, he put one more and then one more. I was comfortable till then. The fourth finger tightened my pussy a bit. But I was enjoying it.
I had totally forgotten that 5 video cameras and a still camera are around me imaging each and every second and moves into the films. I didn’t care about anything then. I was in a mood of nirvana. Now it was time for Steve for his move. He picked me up and made me sit right on top of his huge cock, in such a way that his cock he is pointing directly to my pussy opening. He, holding both sides of my hips, slowly showed me onto his cock. His cock head came out of its covering skin and parted my pussy lips. Slowly it thrust into my hole. It was stretching my pussy hole now. With great difficulty and a very slow pace, Steve’s cock head entered my virgin pussy. I didn’t cry though my pussy skins were stretched. May be Steve didn’t like me not crying. In one shot, he pulled me onto his cock and before me realizing anything; his cock was fully immersed in my pussy. I should feel it touching the ends of my little hole. And it stretched my pussy over the extents. I could not control my cry this time. I screamed loudly. But the soundproof walls of Steve’s studio didn’t let my cries escape out of the room. Before I could realize the situation and what was happening, Steve had started pumping into me. I could do nothing. My small but round boobs were bouncing in rhythm. I supported myself on his thighs. After some time, he stopped pumping. He took his cock out of my cunt. I could feel a relaxation in my pussy. He made me stand like a dog and inserted his dick from my behind. That was the first doggy style I was having. He pumped and pumped with no mercy. I cried, but there was nobody to hear my cries.
He tried different poses with me. When I was a bit relaxed from the tightness, I started enjoying the show. I reached orgasm after some time. My muscles all stretched and I had a beautiful orgasm. But Steve was still on. He continued. At last, after so much of pumping, he increased his speed. I knew that he is gonna come in some time. Then suddenly he took his cock out of my pussy and came and stood near my mouth. He asked me to open my mouth and he started jerking his huge cock in from of my mouth. In some seconds, he threw his sperms right inside my mouth. His sperms were shot one after the other. It filled my mouth and started overflowing onto my naked body. It fell on my boobs and stomach. Some shot on my eyelids and some in my nose. Close up cameras were covering it very minutely and clearly. When he ejected his sperms fully, he squeezed his cock and took the last drop out and then he thrust his cock again into my mouth. When it was thrust in, the sperms in my mouth went deep inside my throat. And I had to swallow it. The salty sweet taste filled me with excitement. I sucked the last drop left inside his cock out. He loved it and said he liked me than anybody he has ever fucked.

That time I was given a sum of $20,000. Steve helped me start an account and deposited my cash in my account and gave me a debit card. Today, I live like a queen among my friends. Money is not a problem for me. I don’t know how many people I have spent my nights with. In the night, I used to get out of a ladder kept near my window to go out and earn some extra money. Steve every time used to get some aspiring guys for me. Wow, it was all so exciting. I have spent time with people from boys to old people who were in their late 60s and even with girls. There are very few things in sex that I have not tried till now. I don’t find any difference as long as it is pleasing to me. I will tell you my other adventures later in my other stories. Expect it soon. Please rank my story good, so that it will motivate me to write my other adventured also.

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