My Best Friend’s Girl

I have been lusting over my best friend’s girl for the last two years. Jillian was a great girl; she was smart, beautiful and very fun to be around. My best friend, Matt, had been dating her for a few years and I quickly found out that they had never fucked each other, in fact Matt was a virgin and was saving himself for marriage. However, Jillian was not; she had wanted to fuck Matt ever since they first started dating. Matt was a very good-looking guy according to many different girls; however, Matt was Mormon and restrained from various activities.

Jillian was very beautiful. She had shoulder-length brownish, reddish hair, beautiful peach skin, and a great body. She was 5’4, had small 34B sized titties, a busty ass, and big, but toned thighs.

Now I care a lot about my image. Although I’ve slept with a lot of girls, I don’t like to kiss and tell. However, one day one of my fuck buddies, Jessica, who happened to be a good friend of Jillian’s, had let it slip that I was incredible in bed. This prompted this sexually frustrated girl’s curiosity to overtake her judgment.

It was the Friday of Spring Break and I was going to a party. I showed up a couple hours late, and as I drank my beer, Jillian had walked up to me. Although she wasn’t drunk, that was my first impression of her. “Hey how are you doing?” she asked in her normal ditzy voice. “I’m good and yourself?” “I’ve been great; has the apartment been lonely since Matt left?” she asked. Matt, my roommate had left on a missions trip to Japan for Spring Break and I had the apartment all to myself. “Yeah it’s been a bit lonely. There hasn’t been much to do besides read and workout.” For the next ten minutes, Jillian and I continued to make small talk.

Finally Jillian said, “Oh. I was wondering-” She paused; she seemed a bit hesitant before she finally said, “I was wondering if you knew why Matt didn’t have sex with me.” This question caught me off guard. “Uhh…I think he’s a virgin and besides, he’s Mormon.” I answered; however, I knew she knew the answer too. But Jillian ignored my comment. “Is it because I’m not pretty? Does Matt have another girlfriend?” she asked. “Jillian…what are you talking about, you’re beautiful and Matt doesn’t –“ she cut me off. “Did you know I have been dating him for 2 years and he hasn’t ever touched me?” I began to think she was drunk, so I just let her vent.
“Yeah, I mean I don’t think Matt hasn’t ever done that stuff.”

“It’s just, I haven’t had sex in a year and I was wondering if you wanted to fuck me.”

‘Wait…where did this come from?! She wants to me fuck me? And what did she mean by ‘hasn’t had sex in a year’? That meant she had cheated on Matt before’, I thought. “Okay Jillian, you’re obviously drunk…”

“I’m not drunk, this is my first drink. I asked Jessica about you and she said you’re great in bed, and you know how to treat her well; and I just wanted to experience it firsthand.”

This girl I had lusted after for 2 years had actually asked me to fuck her; I wanted to, God knows I wanted to, but I had to think about this … Hurt my best friend and fuck his girl or keep things the same with some awkward tension between me and Jillian…before I could logically answer it, my tongue let out the word, “Sure.”

I had to make sure she wasn’t drunk, so I scheduled a time for the next night. Jillian also had a condition; that I had to act like I was Matt. We did have the same body type; we were both Asian, both have a fit body, etc, so it would be easy for her to imagine.

On Saturday, I cleaned up my place. I had to make sure that Jillian was happy fucking me, and I didn’t want to disappoint. That night, Jillian knocked on my door. It was about 10 o clock when Jillian came over. I began walking to my room when Jillian stopped me. “Let’s go to Matt’s room.” She said. I initially didn’t want to since I would have to wash the sheets the next day (Matt came home Sunday night), but because I wanted to fuck Jillian, I obliged. We got into Matt’s room.

“Are you ready?” I asked. Before she replied, she threw me onto Matt’s bed. “What do you think?” she asked as she unzipped my pants and pulled out my unerected cock. Immediately, she started to suck on it. Ravenously, Jillian licked up and down my cock, hoping to harden it quicker. I almost freaked out when Jillian started to gnaw on my penis. As my soft cock began to harden, I reached over and stripped off Jillian’s shirt. She was down to her lacy, blue bra, when she started feeling my washboard abs. As Jillian felt up stomach and pecs, her arms started to pull my shirt up. She took off my shirt and started to suck on my nipples. I reached over and unhooked her bra; her pink, quarter-sized nipples were hard and started to rub against my stomach.
Jillian got off my body and took a step back; she smiled as she took off her sweat pants. I started to take off my pants; my pants and boxers were at my knees when Jillian said, “And now, ladies and gentleman, the main attraction.” Jillian’s light blue thong was magnificent; she did a circle to show me how she looked from all angles. The thong highlighted her perfect, fat ass. She started to take her thong off; her ass was facing me. She slowly turned around and all you could see was her glorious, pink and shaved pussy.

My semi-hard cock apparently approved as it started throbbing up and down. Jillian noticed it immediately and walked up to me. Again, she started to suck on my cock, only this time she started to finger her clit. “Oh God.” She said as drool came down my shaft.

Again Jillian’s mouth left my dick and started going up my body; kissing everything as she went up. She jumped on top of me; her pussy was sitting on my stomach. She leaned her body over and rubbed her small, hard, titties against my face. I started to lick and nibble at her tiny, pink areolas as she wrapped my head with her arms and pushed me closer to her magnificent body. Her pussy left a slime trail as she rubbed it up and down my stomach. Jillian then repositioned her body and her pussy started to rub against my shaft. My cock throbbed, begging to get inside this tight pussy; however, Jillian continued to tease it. I could feel the heat radiating from her magnificent cunt. “How bad do you want to fuck me?” Jillian asked as sexy as she could. All I could think about was how hungry I was for Jillian’s pussy. “This much!” I grunted as I rammed my cock into her tight pussy. It had caught Jillian by surprise as her eyes widened and she let out a high-pitched shriek that implied pleasure and pain as I inserted the full length of my manhood into her. The motion I used was so strong and Jillian was so caught off guard that her body immediately flinched and tightened; her already tight pussy contracted and collapsed around my cock and the sensation felt amazing.

The noise that came from Jillian’s pussy was very close to the squish sounds that one makes while walking in wet socks. I repositioned our bodies until she lay perpendicular to my body. I lifted her leg for leverage and pushed my cock harder as Jillian tilted her head back on the bed. She used one arm to cover her eyes and her other arm to massage her tiny titties. “Oh God, make Love to me” she yelled.

Starting from her flat stomach to her titties, her body rippled in rhythm with my thrusts; her titties would jiggle more rapidly, as I intensified the motion. She let out a satisfied moan; her eyes were still closed, she bit her lips, one hand massaged her titties, while the other one grasped the bed sheets. Then she yelled out, “Matt…Oh my God! Matt!” Her voice got louder with each powerful thrust.

I repositioned my body. Jillian turned around and got on all fours. She stuck out her ass and her wet pussy stuck out from between her legs. I violently rammed my cock into her pussy and pounded on her as I hard as I could. Jillian’s tiny titties started flopping up and down, in complete synchronization with my motion. “Do you like my pussy? Do you like my tight pussy?” Jillian asked. I started to slap her plump ass as my cock came in and out of her pussy.

I pulled out my cock again from Jillian’s soft, hot pussy. I got on the bed and laid down, my cock pointing at the ceiling. Jillian got on top of me; her bald pussy lips began to kiss my shaft; she was spreading her juices all over my cock. Jillian started to tease my cock this time, by taking it a centimeter into her, and taking it back out. My cock started throbbing harder, needing another taste of Jillian’s perfect cunt.

Finally, she put my cock into her body and rode me like a pro. A ripple went through her body, from her chest to her hips to her plump ass as she rode me; the motion pumped my cock like I had never felt before. She started to move her hips sideways and finally went in a circular motion; she was going up and down, side to side and around, finding different ways to pump my body all in one motion. My cock was in heaven; this was the best ride of my life. I tilted my head back on the bed, absorbing the pleasure. I noticed at the corner of my eye that Jillian’s head was also tilted back and her eyes were also closed; no doubt fantasizing that she was fucking Matt. “O my God I love your cock!” Jillian screamed.

I let out a loud moan and she immediately came back to reality. I could tell she was a bit disappointed that I wasn’t Matt; her motion and pace slowed down a bit, and I had noticed that she was less into the sex. Jillian then guided my cock out of her pussy and I grabbed her narrow shoulders. I started to kiss the base of her neck; she tilted her head up with a soft moan. Slowly I moved down and started to suck on her nipples; I pinched one while sucking the other. Softly, her girly voice said, “O my God.” She started to forget that I wasn’t her boyfriend and started to enjoy herself once more. “Make love to me, Matt.” She whispered. She reached down and started fingering her clit. My cock was purple from the fuck; I could feel the pressure mounting and courteously, Jillian started to pump my cock up and down with one hand, while fingering herself with the other.
I pulled away from her and lifted both her legs. I eyed her delicious, wet cunt and stuck my cock inside her once again. I started going in and out of her once again. Both of us let out loud moans as we were approaching climax. Jillian started to massage her clit as I was still pumping inside of her. Our rhythmic motion intensified. Faster and harder I pumped, and faster and faster Jillian massaged her throbbing clit.

Loud moans and the fanatical pounding of our two bodies was all that could be heard. Matt’s bed viciously rammed the wall over and over again. Our breaths started to shorten. Jillian’s moans started getting more higher-pitched and more frequent. I knew she was about to cum and she knew I was about to cum. “D..D.Don’t cUm in…in me” she said. “Where do you want me to cum?” I groaned. “Here.” She said, pointing at her stomach. “Okay” I said. Now I was disappointed; I didn’t want to pull out; the feel of creampie-ing into my women and feeling their pussies orgasm on my cock is what I love most about sex.

I could feel my cock slide in and out of her pussy; I could not go any harder or faster. Jillian’s moans were so quick now that it sounded like she was humming. I felt the pressure build up to critical mass. I pulled out of her pussy, contemplating whether or not I should creampie, but my instincts overtook me. At the last second I pushed in my cock as hard as I could right back into her tight pussy and came. I let out a huge groan and shot strand after strand of cum into her pussy. Jillian’s pussy contracted as ropes of cum entered into her. I let out a huge satisfied groan as my orgasm subsided. Sticky cum mixed with pussy juice clung on to my cock as I pulled out my penis from Jillian’s body. A satisfied grin overtook my face; Jillian’s eyes widened and stared at me. “What the fuck JON! I TOLD YOU NOT TO CUM INSIDE OF ME!” she yelled. With a look of anger mixed with worry, Jillian again screamed, “I’M NOT ON THE FUCKING PILL WHAT THE HELL IS YOUR PROBLEM?!” “Sorry, I- I couldn’t control it!” I lied. “FUCK YOU!!” she screamed as reached into her pussy to try taking out the wads of cum inside her.

Matt never found out that I had fucked Jillian; she didn’t want him to know. It became awkward between Jillian and I for several weeks. I was glad to know that she did not become pregnant. However, after time, in almost a Stockholm syndrome type of ordeal, Jillian asked me to fuck her again. She had enjoyed our time (minus the cream pie) very much. After several fuck sessions, she quickly found out that I had loved creampie-ing. She continued to get pissed whenever I did; however, she finally stopped trying to stop me from my obsession when she started to take the pill.

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