Virginity Lost To [M}y Best Friends [F]renemies

After getting my 1st blowjob from my close friend Jessica I was on on top of the world! Although I was being delusional with the idea that I was something of a player now it did help me lose my virginity with Melissa. Who’s Melissa? Well, Melissa was the Hispanic girl everyone in school would stare. I never admitted it to Jessica that the guys would talk about her much more than her! Jessica and Melissa weren’t exactly friend…I’d call it frenemies, so she wasn’t really into the fact that I though she was hot. Like I said she was hot, In my school she was a Goddess. Melissa had those succulent Hispanic lips and big hazel eyes. Melissa had brown shoulder length hair and large tits. She was average height with a plump butt and she would always wear high waisted jeans and tight shirts tucked in accentuating her figure.

Well like I mentioned in my previous story Jessica had finally given me a blowjob, a taste of what sex could be like so I was on a mission. Weeks of this confidence starts to go down as all my attempts to get Melissa have failed miserably. Well Jessica was enjoying this to no end, she kept telling me it wasn’t going to happen. This and the lack of a second blowjob from Jessica was shaking my confidence. The most I got from her during those weeks was to watch her change her shirt giving me material for jerking off.

Well a few days later Jessica and I are walking down to get a slice of pizza when we run into Melissa. Although Jessica and I hang out everyday this seem to catch Melissa of guard. We make small talk and for a moment Jessica held my arm as we say bye and head into the Pizza place. Honestly at the moment I didn’t think anything of it but after this whole thing happened, Jessica told me that was the moment Melissa noticed me. Jessica said girls want guys who they can’t have, makes sense to me now that I’m older.

After this point Melissa was been super friendly to me and we even started texting. I’m in heaven telling my guy friends that I’ve hit the jackpot. My friends are mostly encouraging with the exception of Jessica. This made her distant from me to a certain extent plus it didn’t help she was now dating a guy. The next time Jessica and I hung out I noticed a condom in her trash bin and it made me feel awkward. Well as we drifted apart me and Melissa became good friend and eventually went on small dates.

This particular date Melissa was wearing one of her usual outfits, high waisted jeans with a black halter top. The date wasn’t anything special we talked about everything and then the topic of Jessica came up. I skillfully avoided saying that we didn’t have a sexual relation. I think that was probably my best move of the night. Once in the car we made out intensely for the 1st time. Her big lips on mine get me hard and I begin to move my hand from her small waist to her right breast. The moment I begin to feel her tit over her top she suddenly drops the seat down. I follow her down and we begin to make out again. This time I push my hand under her shirt and feel her nipple. He nipple is hard and tiny.

I then pull away from her luscious lips and pull her top to side allowing me to see her breast for the first time. They are smaller than I had imagined but probably due to her being on her back. Her areolas were larger and darker that I had anticipated but I was loving the sight. I began sucking her nipples and kissing up to her neck and back. At this point my cock was uncomfortable so using my right hand unbutton my pants and pull it out.

I feel Melissa’s hand on it soon after and she begins to jerk me softly. The third girl to ever touch my cock was a goddess, I was ecstatic to say the least. A part of me was thinking this was payback to Jessica. We continue making out as she unbuttons her pants and pulls them slightly down. I take the hint and begin move my hand underneath her panties and feel her soft pubic hair. She has more than Jessica had when she grinned her pussy on me which made me hornier. I then feel her wet pussy and begin to finger her softly. Melissa closed her eyes and started to enjoy me fingering her clumsily. The view was exotic, her big tit hanging out and her hand stroking my cock as I fingered her.

In a soft voice she Melissa say’s condom. Without hesitation I pull out a condom from the glove compartment. You know the one you keep there because you just never know. Although at that age you really wont use it! Well I begin to immediately struggle putting the damn thing and for a second I think I’ve blown it. Then I feel Melissa take the condom from my hand and place it correctly on on the tip of my cock. I nervously smile and she chuckles and using both hands rolls the condom down my cock. She jerks my cock faster this with the condom on, I’m guessing she was making sure I was still hard.

Melissa then sat up and shift her body over the seat now facing away from me on her knees. I watch her pull down her pants and underwear revealing her tight ass and pussy to me. I still remember every detail of her pussy. Her pussy was shaved, her labia was slightly darker than her skin tone glistening with her wetness. I follow her lead as we crawl to the back of my car. I place my cold clammy hand on her hip making her flinch slightly and miss my first attempt sliding up towards her ass. Although I miss I loved seeing her look back at me with that sexy smile.

It only takes another attempt for me to feel the head of my cock penetrate her tight pussy and I officially lose my virginity. The heat surrounding my cock is incredible as I eagerly thrust inside my first pussy. Placing both hands on Melissa’s hips I begin to awkwardly fuck her doggy style. Melissa begins to moan softly as I build up a rhythm fucking her from behind. Even the sound of my cock and balls hitting her pussy is intoxicating to me. I can feel my orgasm building and for the first time experience the pleasure and pain of balls hitting a pussy. I absolutely love it

As Melissa begins to moan louder my legs buckle and I cum quietly cum inside her young wet pussy. I continue to thrust into her until my cock becomes too sensitive and soften. I pretend to cum at that moment and continue touching as I begin to pull out of her pussy. Melissa immediately pulls her pants up and turns to me asking if her pussy was better than Jessica’s. Caught off guard I didn’t answer right away making her upset. My answer of yes didn’t matter after that making it tense moment.

Well we dated a few more weeks but ultimately that one question ended what could have been something amazing. Fortunately for me that one question made a difference in my relationship with Jessica.

Source: reddit.com/r/gonewildstories/comments/7puu1v/virginity_lost_to_my_best_friends_frenemies