This is my first story. I've been wanting to start writing for a while now. Wrote it in one sitting and didn't reread, so sorry for mistakes or incongruencies! Appreciate all suggestions and criticisms (even spelling or grammar errors please!)
*****
There aren't many things in the world I love. Truly love. I'll enjoy something a lot; rock climbing, flying, sports, video games, etc. I'll spend a lot of time doing those things, and may stick with them for months or years at a time, but, eventually, there is always something I'd rather be doing.
Massages are one of those things I love. Sex is another. Physical contact is something I crave. And sex is something I'm good at. Like most men, I had always fantasized about fucking my masseuse. Of course, paying some Thai hooker wasn't the same as it happening organically, so I figured it was one of those things that would never happen.
Shannon, prior to our first date, was the embodiment of everything I wanted. A newly minted massage therapist, obsessed with physical touch, constantly horny (or twirly as she would eventually label it), and smoking hot to boot. She was 5'3" and 109 pounds. Small, tight breasts that felt perfect in the hand and an ass you wanted to bury your face into. Topped off with a stomach that you could ALMOST see the definition in, shimmering shoulder length brown hair, lips that you just wanted to see wrapped around a cock, and hairless from the neck down... She was, physically, just about perfect.
On our first date, we had wine at a park. I had a blanket in the back of my car for just such occasions. The conversation was fluid and dynamic. The first kiss was delicious. And the windows were nicely fogged after we started messing around in the car. I stopped it, because I'm a gentleman, but she later told me she would have fucked me right there in the car. Looking back, I don't remember why I stopped it, but I remember it being the right decision.
While Shannon was physically everything I wanted, the rest of it left a bit to be desired. I'm no prize, but I have high standards; too high. I'm on the shorter side at 5'8", but I'm built well enough to pull it off. Short brown hair capped a smile that usually did some pretty good work for me.
At the time we met, I had just been rebuffed by another girl, and I never take that well. So here I was, insecure and average looking, but when I managed to turn it on, I turned it ON. I can be rather charming when I get out of my own head, always been on the smarter side, could carry a great conversation, and what else... Oh yeah, I'm a fucking fighter pilot in the Navy. That always managed to get some interest. Admittedly, more from the guys than the girls, but it worked on the ladies well enough to suit my needs.
Back to Shannon. She was gorgeous, fun, and ready to fuck, but she wasn't REALLY ready to fuck. Shannon was highly, highly religious. Talk about a split personality! She wasn't a virgin, but anybody she had sex with she ended up bailing on pretty quickly. She ended up feeling guilty. So she'd had sex, but not a lot of it. The one bright side was that other stuff didn't constitute sex to her, and I liked to push the boundaries.
We dated for a couple months. We started with kissing and oral sex, but, every date, I pushed it a little further. At first, it would just be dry humping. Sliding my cock along her delicate, clean, shaven lips. I would finish in her mouth (of course she swallowed). Soon, I was pressing slowly, achingly slowly into her. I would push a bit, and she'd stop me. We'd frequently end in the shower, where I'd rub my cock between her ass cheeks until I came. She loved that. Once or twice, I went balls deep if we were drinking. I know what you are thinking at this point; that's sex! She thought so too, but not enough to end it. We messed around a LOT in those three months. Occasionally, I would be buried inside Shannon, but never got to cut loose and just have my way with her.
She also dug anal, but that's a story for another time. I was always decent at oral sex, and I loved giving it, but I got really good at it because of this girl. I got adept at licking and sucking the clit with two fingers doing good work in her pussy and my pinky in her ass. Never failed to make her (or any other girl barring one) cum with this technique.
Even though I loved giving, I'm not a huge fan of receiving. But it was all I had. She sucked me off at my house, at her house, in the car, and anywhere else we could find a hint of privacy. One time, early when we started dating, she swallowed a load at her job. She was very nervous, because she could get fired, but the thrill made it all the sweeter. Anytime we drove somewhere, my fingers were exploring the perfection that was her pussy. As you can imagine, this left a great deal of frustration. I had hoped to wear her down, but every time I bottomed out in her, the next day she would say "we went too far", and I'd have to start slowly from the beginning again. I never had the chance to cum inside her, and trust me, she had a pussy that just milked a cock for everything it was worth.
So, why am I reminiscing about this girl? We broke up after about half a year. The reason? We got hammered, and we "had sex". Even drunk out of my mind, and Shannon begging for it, I still couldn't get over my "good guy" hump. Ok, "decent guy". She didn't to have sex, and it seemed that splashing inside her was the defining factor, so I didn't. Anyway, I had her in every position, missionary, doggy, on the side, against the wall, her on top, just about anything. I figured we'd had sex, and crossed the point of no return, and could start doing it in earnest, but she had other plans. She basically started me back to ground zero, just like she always did. That was what broke me. I ended it.
It was one of the hardest things I had ever had to do. I loved her, she loved me, and just about everything was perfect, but I didn't want to feel guilty every time I had, or tried to have, sex with my girlfriend! Plus, despite me insisting that she not, she was trying to convert me to her religion, and fuck that.
Breaking up with a girlfriend is hard. But losing your massage therapist at the same time? That was brutal. The job put a lot of strain on my body, and I got them every couple weeks. I had always used Shannon, and she was the best. 5 years later, and I haven't found anybody her equal.
I have dated people since her, but none had that same quality she had. None of that innate sexiness and eagerness to please, and that desire to BE pleased. Naturally, I imagined many many times, fucking that girl and cumming inside her.
I moved away a couple years later. We talked a couple times, at first with a lot of friction, but soon after, fairly amicably. She was engaged now and she seemed happy.
Prior to leaving, I had purchased a house, and rented it out when I moved away. After a year, my tenants were on the verge of moving out and work had me in the area, so I figured I'd pop into the area. After my business was done, I was thinking about what I could do on my last day before heading home, and I figured I'd get a massage.
Naturally, any time I think of one, I think of Shannon, but she had put the kibosh on it happening again. They can be very chaste, but, with the right situation, extremely sexual, so I didn't blame her. Still, I figured enough time had passed, so why not?
I messaged Shannon, told her I was in town and looking for a massage, reminded her that she was the best, and asked if she'd be willing. She seemed to hesitate a little, but I guess she remembered she was happy now, over me, and wasn't willing to turn away a good tipper! We had an appointment for 3:00.
I was disappointed to find out she still worked for one of those chains. She was far too good to be wasted there. I had wanted to push her into her own practice, but she wasn't the ambitious type.
When she greeted me, she was very professional. She still looked amazing. She had highlighted her hair, and she wasn't the flawless 23 year old I had dated, but her skin was still smooth and her body was still incredibly tight. She wore the company uniform, unrelieved black; form fitting black yoga pants and a black short sleeved t-shirt.
Just as fuckable as she always ways.
One major change that caught my attention was a small diamond ring at her throat.
