Sexploits Ch. 03: Jessica

A couple years ago, I posted a story about my first group sex experience and stated that it was the first time I had a sexual relationship with my friend Jessie. While the story itself was true, that particular fact was not. At the time of the writing, there were personal reasons as to why I omitted the fact that I had actually slept with Jessie previously. However, those reasons are no longer of concern. The following is the accurate account of the actual first time I had sex with the object of my longtime obsession:

I made it home just before the weather really took a turn for the worse, thanks to the fact that work sent us home early in preparation for the snow. My two roommates, who worked together at another company, were not quite as lucky. Unfortunately for them, they would be stuck at their jobs overnight until this blizzard, which had onset suddenly, passed over. Little did I know that the stars were aligning for what would be, at the time, the most memorable night of my life.

By 5 pm, all the roads in town were shut down. It was around that time that I got a phone call from my friend Jessie. Jessie and I had a pretty long and very complicated history, but I considered her my best friend. However, even though we texted often, an actual phone call was a very rare occurrence.

I picked up immediately, and Jessie, who worked literally less than a mile from my apartment but more than a half hour away (in good weather) from her place, was calling to ask a favor. With no reasonable way for her to get home, she was asking if I or my roommates would mind if she spent the night at our place until the storm was over. Of course I told her yes, because what decent human being would deny such an urgent request? What I didn't tell her was that my roommates were stranded elsewhere for the night. You see, my heart started pounding and my throat got tight the second my brain processed Jessie's request because I wanted nothing more than for her to spend the night. Given our history, though, I didn't want the fact that we'd be alone to deter her from making what she might have thought was a bad decision.

Jessie and I had been very good friends for nearly eight years by this point, but an unspoken, mutual attraction had always caused a certain level of drama and sexual tension between us. Even though I deeply loved and cared for Jessie more and more as our friendship developed, I never made a move toward a romantic relationship because she had always had a boyfriend, though it was hardly ever the same person until she met Brian. Not only did Brian keep me at bay, he shattered any hope I ever had of being with Jessie when my best friend accepted Brian's marriage proposal a couple years back.

Oddly enough, the closest I came to winning Jessie for myself was mere months before her wedding, when she confided in me the insecurities she had with her soon-to-be groom as well as her very real and deep affectionate feelings for me. We even talked openly about having sex, which would have made me happier than anything else in the world. After all, Jessie was not only my best friend; she was the object of all my sexual fantasies, no matter how ordinary or downright depraved those thoughts were.

Beside our obvious chemistry with each other and the multitude of things we had in common, Jessie was easily the hottest girl I had ever met and she was exactly my type. At 5'5" and thin with slightly tanned skin, she had perfect, straight, long brown hair that reached her shoulders, bright brown eyes and the prettiest lips and smile a girl could have. Her rack was admirable for a petite girl, and her legs and feet were as sexy as any I have ever seen. I could only imagine how much fun she was in bed.

However, not only did Jessie and I never come together physically, she did end up marrying Brian, and our friendship took a huge hit as a result. In fact, it took about two whole years until we were completely comfortable around each other again. However, once we were back to texting and occasionally hanging out, those old feelings started to creep back into my heart. I often wondered if Jessie felt the same way.

This particular week, Brian was away on a business trip, as he often was. Not only would Jessie be at risk of being stranded at work, she didn't have anything to go home to or anyone to come get her. I was happy she had turned to me, and, with the setup perfectly coming together, my mind began swimming with the thought of having my sexy best friend all to myself for the night, although I realized I had a snowball's chance in hell of even getting Jessie to consider anything remotely adulterous tonight.

Even though she was not even a mile away, it took almost half an hour for Jessie to arrive in the thick snow. I finally noticed the headlights fighting through the flurry in my driveway and I hurried to the side door to help my former love interest into the apartment. As soon as my eyes caught sight of her, my heart melted as I pitied the poor young woman in her mid-20s who was wet, freezing and miserable. When she finally had made her way to the door and into the house neither one of us said a word at first. I simply helped her with her jacket, which I draped over a nearby chair in my kitchen.

When I turned back around, I saw that Jessie was shivering uncontrollably, the color drained from her face. In empathy, I took her in my arms and held her to help warm her up. I wasn't intentionally romantic, but the embrace reminded me of the hugs we had shared in the past and how it always felt like the world stopped when we embraced. This moment was no different, and all those old feelings can rushing back in an instant.

Jessie's shivering grew less and less, and the married woman simply held me back as she warmed up. I couldn't help but rub her back in a comforting manner as I observed what she was wearing. I still remember the knit, turquoise sweater, dark blue jeans and black boots she wore that night.

It then became very apparent that the hug affected Jessie like it had me because, just as I started to pull away, in a moment of weakness, Jessie leaned up and kissed me on the lips. Even throughout the emotional roller coaster we had endured the past several years, we had never kissed. I knew what we were doing in this moment was wrong, but it felt so good to finally kiss my best friend that I savored the moment, figuring it was brief and fleeting, never to occur again or harm anyone.

"I'm sorry," Jessie said softly when she finally pulled away.

"Don't be," I said quietly.

"I'm just in a really bad place emotionally right now," she tried to explain. "I'm so sorry, I--"

"I said don't worry about it," I cut her off. "It was nice." I then quickly changed the subject and let her know what kind of food there was to eat, although you can imagine a bachelor pad didn't offer a very wide range of delicacies. Also, while I had little to provide as far as entertainment, there was always Netflix. Then I finally told her that my roommates wouldn't be home tonight.

Jessie's eyes went wide, and I swear that her mouth curved into the slightest of smiles for just a second when my friend realized we would be alone. She quickly composed herself and realized she had yet to thank me for my hospitality, so she did so as she removed her boots.

"You're welcome," I said. "You could probably use a shower, huh?" I added. Jessie gratefully accepted, and I got her set up in the bathroom that was just a stride or two away from the living room where I would be. Since the only clothes Jessie had were the wet ones she would be taking off, I gave her some of mine, even though they would be really big on her. She smiled, thanked me again and then closed the door.

Once the bathroom door was closed in front of me, I exhaled and looked down, noticing right away the huge bulge in my pants. I was embarrassed, realizing that there was a very good chance that Jessie had noticed my erection. After a few more deep breaths to help calm myself down, I headed the couple steps over to the living room, sat down on the couch and turned on the TV.

Nothing on that screen could distract my thoughts, though, especially once I heard the water in the shower turn on. There wasn't a girl in the world I would rather fuck than Jessie, and not only was I all alone with her in my own apartment for the night, she was naked and wet on just the other side of the wall to my right! The longer she was in there, the more I tried to desperately formulate a seamless plan to convince her to have sex with me tonight, her marriage no longer a deterrent to me now that we had kissed. The intensity of my lust had never been higher since meeting Jessie so many years ago.

At last, I was getting so anxious that I realized how ridiculous I was being. There was no way another man's wife, even if we were best friends, was going to sleep with me tonight. I finally made up in my mind to take this night for what it was meant to be: a nice opportunity to just be comfortable and hangout with my best friend without doing anything stupid that could adversely affect the rest of our lives.

My chest got tight when I heard the water shut off, and I prepared for my friend to join me on the couch. Even though I had calmed myself down to the point that I was genuinely eager to just hang out with my friend, it was hard to beat down my flesh that wanted so badly to make it with Jessie tonight. The fact that Jessie took forever getting out of the bathroom only compounded the anxiety that was now rebuilding within me. At last, the door swung open, and everything changed.

I think my jaw hit the floor when Jessie at long last emerged from the bathroom. She wasn't wearing my clothes like I had expected her. She wasn't wearing her own clothes either. She wasn't wearing any clothes at all! Her hair hung down still damp, and her eyes and smile were bright upon her face as I took in her naked body, which was every bit as beautiful as I had always imagined, from her perky breasts to the slight curves of her hips.

Obviously, at this point, my lust got right back in the driver's seat, and my cock sprung to full life in my pants. I was as utterly speechless as I had ever been in my entire life. Jessie remained silent too but eventually began to strut toward me, her bare feet lightly slapping against the hardwood floor.

"I wanted to thank you for taking care of me tonight," she said, finally breaking the silence. "You've always been a great friend." I didn't even bother to ask her if her husband would be OK with what was happening. I knew I should have talked her out of it, but my flesh was much too weak to pass up on Jessie. Before this night, I had made up my mind that I would never, ever have sex with another man's wife. However, when I made that promise, I never imagined Jessie would throw herself at me like she was in this moment. I quickly decided I would make an exception.

The next few moments were quite a blur, but before I knew it, Jessie was on the couch with me, leaning into me as we kissed. I pulled away only for a moment so I could take my own shirt off and then dove right back into tasting that delicious mouth. As my tongue fought with Jessie's for space past her lips, I gently pushed my dear friend onto her back, her boobs pressed against my chest as our arms wrapped around each other. Her flesh was slightly damp and very warm from the hot shower she had taken, beckoning me in even more. It all escalated so quickly that my mind was whirling with the realization of what was happening. It was hardly registering that I was finally making out with the girl over whom I had obsessed and fantasized all these years, and that the best was just around the corner.

I retreated from that embrace in order to again take in the lovely site of my naked friend, who smiled back up at me while her breasts heaved up and down with exhilaration. We didn't say any words to each other. We didn't need to. The chemistry we had developed over the past several years had brought us to the point where we each knew what the other was thinking just from the expression on one's face or the look in one's eyes. In that moment, as I gazed upon that hot body and gorgeous face, I knew Jessie was inviting me into her most intimate of places, and she knew that I was willing and eager to go there.

My eyes traveled from the top of Jessie's head to the tips of her toes, all of it intoxicating me. As I made up in my mind to move forward with fucking my best friend on that couch, I looked down at her feet and had another idea. First, I leaned forward, putting my hands on Jessie's tits and squeezing them before my mouth made its way to them. Jessie squirmed and giggled as I massaged her breasts and then started to suck on her nipples, going back between the two. As my head switched from boob to boob, so did Jessie's head, turning to watch me as I further aroused her.

Next, I traveled down her body, kissing down her stomach until I reached her vagina. Her scent emanated from her womanhood, which I could see was already wet. My hand traced down to her clit, where my thumb rubbed against it while my tongue pressed against the opening to her center of sin. Jessie groaned loudly and writhed a bit more on the sofa as I started to lick her pussy for a few minutes in order to really get her juices flowing. All the while I fought feelings of shame and guilt, knowing it was wrong to do what I was doing to another man's wife. However, I had dreamed of this moment for so long that nothing could dissuade me.

When I finished eating Jessie's pussy, my hands ran down her thighs as I knelt back up and pulled my hands away quickly to undo my pants and hastily take them off. Out sprung my erect cock, which made Jessie's eyes and smile get wider. Still no words were spoken as I put my hand back on Jessie's legs and slid them down until I was grasping her ankles. Then, with my cock sticking straight out, I lifted Jessie's feet up and placed my prick between them as I admired her French tip toenails.

Jessie giggled some more and squeezed her boobs, her drying hair splayed around her head as she relaxed and allowed me to shift her feet up and down the shaft of my cock as I moved her ankles up and down. I had revealed to Jessie years ago that I thought she had the prettiest feet I had ever seen, so though she wasn't expecting to give me a footjob, she wasn't surprised when I took that liberty. My eyes went from Jessie's eyes, down to her tits that she was clutching and then down to my phallus between her cute feet. There was something undeniably sexy about Jessie's smooth, dainty feet sliding up and down my shaft.

After a couple minutes, I lifted Jessie's right foot up to my mouth and licked down the top of it until my tongue reached her toes. Then I did the same to her left. She laughed and said, "I think that's really sexy," as she squirmed. My nerves dying down more and more by the second, I continued to play with in that manner until I couldn't stand any longer to deny my penis of what it had been longing for this past near-decade.

"Do you want to do it here or on my bed?" I asked, putting Jessie's ankles down.

"The bed sounds more comfortable, doesn't it?" she answered, still smiling.

I jumped off the couch and led Jessie into my bedroom by the hand, turning her toward the bed as soon as I turned on the light. In another moment of blurs, I pushed Jessie onto the mattress and hopped into bed with her, just like I had imagined hundreds of times before in my head. For the first time, it was real life, and thus far it had been everything my dreams had hoped.

At a manic pace, I lay on my back as my best friend got to her knees beside me and threw back her beautiful, long hair. My heart felt ready to burst in my chest at this point as I couldn't stop admiring that rocking body. When my eyes caught hers, she smiled warmly and then reached out to take my cock in her hand. So aroused was I to finally be naked in bed with Jessie that the mere touch of her soft hand against my rigid penis could have been enough to make me cum, but, fortunately, I was able to compose myself as Jessie began to stroke my manhood. Her hand slid slowly up and down my shaft, occasionally slipping down to gently rub my balls while the pretty brunette continued to smile at me as I moaned with satisfaction.

"You want a blowjob, don't you?" she said, still smiling. I had actually been thinking about how badly I wanted to be in her pussy, but she was right in the sense that I had long fantasized about my sexy friend's sucking on my cock, and she knew it. I couldn't help but grin and nod my head, still struggling to produce words in the midst of this unbelievable experience. Words weren't necessary right now anyway, and I simply watched on as Jessie pushed her hair behind her ear, lowered her head and opened her mouth wide.

Gripping the sheets beneath me, I cursed loudly and moaned as Jessie's pretty mouth took my prick in, and her head began to bob up and down. Her wet tongue pressed against each vein in my shaft and danced against the tip each time her head shifted back up. For the next few minutes, the only sound was Jessie's slurping on my manhood and the occasional irrepressible moan from my own mouth as Jessie gave me a blowjob as good as I had always imagined. After all, she had told me before that she was good at sucking cock, and I had no reason to disbelieve her, even before she masterfully polished my knob with her sexy mouth.

Jessie edged me for another minute or two until I could no longer restrain from venting the entirety of my love and lust upon my hot friend, whether she was married or not. I told her how badly I wanted her to fuck me, and she giggled as she pulled her head away from my prick and relaxed her grip on it. It seemed as if she were about to say something, but she didn't. Instead, she kept her eyes on my penis and straddled me, holding my cock in place just beneath that gorgeous pink and wet pussy that I had for so many years longed to penetrate.

Jessie pursed her lips and looked me right in the eyes, her bright brown eyes beaming as, after what felt like an eternity, she lowered herself onto me. If it were possible, my heart would have pushed right through my chest in that moment of anticipation, so excited and aroused was I. I cursed again the instant my tip pushed into her wet folds, and we moaned in unison as she lowered herself down, inch by glorious inch, until my cock was completely inside my best friend.

We both moaned loudly as my cock adjusted to Jessie's insides. Granted, it was still only one of the first few times I had sex, but regardless, I had never been more excited to be joined to a female than I was in that moment. This time it was Jessie, the girl whom I had loved for so many years. My cock was wedged deep inside her in real life, and we were actually having sex, not just talking or thinking about it. My mind, heart and cock were nearly overwhelmed, but Jessie, undeterred, slowly lifted that thin, tight body up until just the head of me was still in her, at which point she slid back down just as slowly, shooting all manner of pleasure through my body.

"Fuck!" I yelled. "Jessie! Ride me!"

"Like this, sweetie?" she said, going up and down my cock faster and harder.

"Oh my gosh, yes," I affirmed her. As Jessie bounced faster and faster on my cock from her knees, her boobs and hair flew up and down as well. I had always though she had such beautiful hair and I had always desperately longed to see her breasts. I was not in the least bit disappointed as my ridiculously hot friend rode me nice and hard, her body slapping loud against my hips each time she came back down on me.

I reached up and grabbed Jessie's boobs, squeezing them hard as Jessie laughed and continued to fuck me. My mind was still whirling with disbelief as my pretty friend made love to my cock, coating it with her sweet juices. Eventually, I slid my hands from those lovely boobs to her shoulders and pulled her down on top of me. As she lay horizontally upon me, she continued to grind hard on me while I now pumped hard and fast into her tight, wet pussy.