An Unforgettable Morning with Annabelle

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1 likes 3013 views Category: Male-Female Tags: Online, Feel, Rub, Slit, Finger, Lust, Spank, Cum, The Urge to Masturbate, Dorm Room Eavesdropping

This is one of my favorite and probably most jerked-off to mutual masturbation encounters. I'm sorry for the length, but I hope you enjoy.


Annabelle and I started chatting online on a Tuesday evening in the middle of March. She responded to my posting looking for a woman who was interested in, to put it bluntly as I did in the ad, having me finger her to orgasm.

Annabelle quickly introduced herself as a graduate student studying in the city. She sent me a photo of just her long, slender legs peaking out from under a nearly knee-length black dress, ending in a pair of perfectly manicured feet in orange-strapped sandals. As soon as the attachment opened I felt the raw lust building and growing inside me. I collected myself and quickly responded, asking when we could meet in person. She agreed that we should get together, but despite my pleading she wasn't free that night, or Wednesday, or even Thursday. Friday though, Friday morning she wanted to meet.

Just the thought gave me another rush of adrenaline, and that happened over and over again as we continued exchanging pictures, fantasies, and masturbation techniques via email for the next two days. Her face was gorgeous: strawberry blonde hair, blue-green eyes, and high cheekbones framing her warm smile. Her turn-ons: foreplay, biting, hair-pulling, teasing, and the one that ended up surprising me the most by how excited it made me, spanking!

Finally, it was Thursday night. I had spent 48 hours refreshing constantly to check for her emails and anxiously anticipating meeting her on Friday morning. She suggested we meet in a trendy coffee shop in her moderately busy downtown neighborhood. She told me she would be wearing an orange dress and would be hard to miss.

We stayed up late emailing each other and I still thought she must be far too good to be true, so I satisfied myself with fantasizing back and forth with her about our meeting. I slowly worked my cock as we arranged to meet in the corner by the window in the cafe. We would sit, chat for the minimum amount of time, and then walk to her place a short distance away. On the way there I asked that she walk "a little too close"? to me so I could grope her ass walking through her crowded neighborhood. Then we would head up to her place, and I asked her to stick her tongue down my throat in the elevator or the stairwell. She told me gladly, and that her building has an elevator. Our fantasizing finally stopped when our fantasy selves made it to her place and I started undressing her and slowly playing with her body. I came, said goodnight, and finally got to sleep.

The next morning I woke up early and reminded work about the doctor's appointment I had told them about on Tuesday evening. I was far too nervous and jittery to eat or drink, so I took a can of soda in the car with me and headed downtown. I arrived about fifteen minutes before we had arranged to meet and I emailed her from my phone. She quickly responded that she was already there waiting for me. Still sceptical, but certainly hopeful, I chugged the soda, found a parking spot not far from the cafe, and headed in.

As soon as I walked into the crowded cafe I saw her. I didn't believe it. She was real. Not only was she real, but she was somehow better than I ever could have imagined. She was taller than I thought she would be, perfect for my unusual height. Her skin, except for a light birthmark on her upper left cheek, was somehow even more flawless than the photos had captured. She was stunning in her bright orange spaghetti strap dress. The fabric draped loosely over her smallish, but amazingly perky breasts and a clear view of her stiff nipples revealed her lack of a bra.

Our eyes locked and she smiled as I approached, only encouraging me to continue taking her in her long legs, perfectly painted toenails, and her confident posture. I sat down, nervous and noticed her shaking her leg as well, clutching her tiny coffee in a disposable cup. We said hello and I can only assume thought the same thing "I can't believe I'm really doing this". We chatted for a few moments, one of the only parts of our morning I don't remember all that well, and I asked her if she was nervous. She said yes and I told her that I was quite nervous as well. "Want to go to my place now?"? she asked, smiling up at me as much with her eyes as with her beautiful lips. "Absolutely,"? I replied, and we stood up. I followed her through a maze of tables, marvelling at the view of her pale ass and black thong through the relatively sheer fabric of her orange dress.

Once on the street she indicated the direction to her place and we started walking. Sure enough she started walking closer and closer to me. I held a straight line and in less than half a block we were walking shoulder to shoulder. I glanced down and she smiled at me, a smile both mischievous and approving that gave me the gall to reach down and gently squeeze her ass through the soft fabric of her dress. She giggled at the excited look on my face and leaned into my shoulder, relaxing slightly. We walked in silence a few more blocks to her place and she quickly led me into a classy new condo unit and pulled me into a large elevator. She grabbed the back of my head and started kissing me deeply. My senses were overwhelmed as I inhaled her sweet perfume and felt her soft lips and tongue against my own.
When we finally made it to her condo she was still trembling a little as she explained that her roommate who enabled her to live in such a fancy place was away for the day and we had the whole place to ourselves. I approached her, heart pounding, and kissed her passionately as I started lifting her dress up and off of her. We broke our embrace and she raised her arms, allowing me to pull her dress all of the way off and toss it aside, leaving me to gape in awe at her slender figure and perky, pink-nippled breasts. I groped her as we continued kissing, squeezing her breasts and pinching her nipples, then ran my hands down the gentle curve of her waist and traced the edge of her panties between her legs. She reacted by standing on her tip-toes, spreading her legs and pushing my hand along the length of her panty-covered slit. I felt the warmth and dampness as she began rocking her hips, grinding her pussy into my hand.

Suddenly she grabbed my hand and led me over to her couch, sitting me down next to her. I continued to take her in, rubbing the insides of her thighs with both hands as she sat facing me. She pulled her panties to the side and exposed her beautiful pink pussy. She had moderately large and perfectly rounded outer lips and was entirely shaved except for a small landing strip of light blonde hair. I looked her in the eyes and found her returning my lustful glare, so I licked my pointer finger and plunged it between her glistening lips. She gasped and threw her head back, spreading her legs further and further as I slowly worked a second finger into her and began rubbing her clit with my thumb. When I curled my two fingers up inside her and began to feel for her g spot she began to squirm, grasping at the couch and gyrating her hips against my fingers. "Oh, that feels sooooooo good,"? were the first words she said with my fingers tickling her g spot as her entire lower body shuddered involuntarily.

I slipped my fingers out and she collapsed, panting with her pink pussy already beginning to swell up and dripping with her moisture. "What should I do?"? she asked me, giving me a helpless look. I told her to take off her panties and bend over my lap. She immediately obeyed, tossing her panties to me, which I sniffed and then tucked in my pocket, and then bending naked over my lap, giving me my first good look at her perfect ass as she rolled her hips forward, raising her ass and exposing her wet slit. I raised my hand and came down hard on her right cheek before she was expecting it and she gasped. I gave her a few more whacks and each time she gasped, but also gave an excited "yipe"? of sorts after each swat. I slide my fingertips down along the length of her pussy lips and began rubbing her clit with the tip of my finger as the rest of it rubbed against her pulsing opening. I turned my hand over and slipped two fingers in, again tickling her g spot. She curled up on my lap and grabbed her ankles between my legs as her whole body shook. I continued like this for some time, spanking her, finger-fucking her, and rubbing, pinching, and slapping her clit. The whole time my dick was getting harder and harder, straining against my jeans as Annabelle's perfect naked body pressed against it.

After a long while she begged me to give her a break, and considering the pink, raw state of her ass cheeks and her bright red little pussy I consented. She uncurled from my lap and sat erect next to me on the couch, leaning on my shoulder and catching her breath. "That was amazing, What can I do for you?"? she asked. I nonchalantly suggested that she should play with my cock and she promptly began rubbing the bulge in my pants. She stroked the length of my shaft through my tight jeans and then leaned down and I felt her hot breath on my dick as she kissed the length of it through the denim. I slumped back and she undid my belt and unzipped my fly, looking up at me innocently with those stunning eyes as she flopped out my hard cock and began eagerly stroking it, seemingly fixated on it completely. She slid off my pants and then bent down and began sucking the head of my dick vigorously as she firmly gripped and stoked my shaft. I was worried about cumming too quickly, but I knew with her submissive tendencies I could get her to give me a break without any embarrassment. I asked her to rub my balls and she did, using the perfect amount of pressure as she squeezed them. Then she dropped down onto her knees between my legs and began sucking my balls, something I had never experienced before and quite enjoyed.

After giving each of my rather large testicles a good sucking, Annabelle proceeded to work her way up, sucking the side of my shaft all the way to the tip before slowly engulfing my 7"? erection. She gagged, and choked, and drooled as she proceeded to give me the most amazing blowjob I have ever had. It was my turn to grab handfuls of the slipcover as she brought me closer and closer to the edge, always stopping short at just the right moment to lick my balls or give me a few good strokes with her hand.

She then laid down on her back and spread her legs wide, she motioned me closer, and closer, and closer, until I was kneeling on her bed with my pulsating cock head less than an inch from her lips. "Cum on me baby,"? she begged, I asked where and she said "wherever you want, Baby,"? and smiled up at me before kissing the head of my cock. I began to jack off, slowly at first, with my dick aimed right at her face. She turned slightly towards me and took the head of my cock in her mouth, sucking hard and swallowing all of the precum that had been oozing from the tip. As she slurped at the end of my cock I stroked faster and faster, rarely breaking eye contact with her and thinking, does she even know my first name? I didn't care, and not caring excited me even further. I jacked harder and harder, my movements jostling my cock head against her throat and teeth as she continued to suck me vigorously. Squeezing her pink, erect nipple with my free hand I finally came, erupting one of the biggest loads I have ever shot into her mouth. She winced, closed her eyes and grabbed my shaft and pumped it as she kept sucking, my semen blasting against the back of her throat. She kept stroking and slurping until long after I was dry and then, still with her eyes closed, opened her mouth and showed me the massive load she had sucked and fucked out of me floating on her delicious tongue. She opened her eyes and looked at me, closed her mouth and smiled briefly before throwing back her head and swallowing the soupy mouthful of my cum. I bent down and kissed her deeply. She stuck her entire tongue in my mouth and I will never forget sucking the salty residue of my spunk off as we kissed. I was no longer nervous, but instead exhausted, and more satisfied than I have ever felt in my entire life. We kissed and cuddled and chatted for a while and then I got cleaned up, got dressed, hugged and kissed her deeply goodbye, and walked out.

All I could think about was seeing her again, and as I walked back to my car I worried that I never would. I went back to work and thankfully it was a slow day. I spent most of it locked in the bathroom, smelling Annabelle's wet panties and her juices still all over my cock as I tugged my sore member off a few more times, quietly moaning her name.

Unfortunately I never saw her again. I waited a few months before emailing her again and just never heard back. I still spend a lot of time masturbating to memories of our encounter. I would love to hear your comments, especially if it helped get you off, and I would be happy to write about more of my experiences.



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