Gender: Male Age: Secret Location: NY
One year for thanksgiving, my family was going to be going out of town to meet with some other relatives for a nice quiet retreat to a cabin up in the mountains. Seeing as how the majority of my cousins my age weren’t going, I decided to decline the invitation. Thanksgiving was getting closer and one day I got a call from a friend of mine, Nicole. She asked me about my plans for thanksgiving and I told her I would probably just stay home since all my family was going out of town. She told me that her whole family was getting together and that I was more than welcome to join them. I had met her family before and they had always treated me very well. I had a couple inside jokes with them and they always made me feel very welcome, even more so than some of my own relatives. We worked out the details I would be staying with her and her roommates for a few days at her apartment during the week of thanksgiving.
The day came for me to head up there and my family dropped me off at her apartment on their way to the mountains. Nicole and I had never had any kind of romantic association despite how much I may have thought about it. I loved her family, they seemed to love me, Nicole was great, but we just never made that level of connection. Every time I got to see her, she was always dating some random douche bag. Needless to say, it just wasn’t anything that was going to happen I guess. She had to work most of the days I was up there so I spent most of the time just hanging out at her apartment while her roommate invited his friends over and they spent incessant hours playing Halo 3. I was going insane. That’s all that they did for hours on end. I was going stir crazy. I had to get out. I got on craigslist and solicited some advice from anyone willing to give up as to things I could do in town and places to go. I got 3 good responses, and they will each formulate a story. Here’s the first.
A girl by the name of Candy had emailed telling me her email connection was a little screw up so the favorable thing to do would be to call her. She left her number and I didn’t hesitate to call her. We chit chatted about, making small talk, and she gave me the name of a few bars in town I could check out. I asked her if she wanted to go have a drink with me and she quickly denied. She told me there was a certain amount of privacy she had to keep as to her profession. I asked her what she did for a living and told me she gave massages for a living. This didn’t really make sense to me so I asked a bit more about it and it came out that she was a call girl that gave massages to the majority of her clients and occasionally a little more. I laughed a bit about it and told her I probably gave a better massage than she did.
“Is that so?” she said.
“Well, I could show you but you’d have to go to dinner with me.”
“I’m not sure that I can do that.”
“I’ll make you a deal.”
“And what’s that?”
“We go to dinner, and afterwards, if you’re feeling up to it, we go back to your place and I’ll give you a massage. If it’s not that great, then I’ll pay you for your time for the evening. If you like it, you have to give me a massage and no payment incurs. Then we can see who is better.”
“I don’t know about that.”
“Sounds to me like someone doubts her skills.”
“Ok, fine. Challenge accepted.”
She picked me up later that evening and we went to a local restaurant to eat. She had never sent me a picture and I wasn’t expecting her to be all that great looking. My luck wasn’t that good. Well, tonight my luck had struck. She had long dark curly hair, which if you have read any of my previous stories, you know that I have a soft spot for that. She was wearing tight pair of jeans and as she was sitting down in her car I didn’t really get a great look at the lower part of her body, but she definitely seemed to take care of herself. My eyes went up to her breasts and she had an amazing set of what I assumed to be 36 DD. They looked great in the tight halter top she was wearing. We ate dinner with the usual small talk, getting to know each other for a bit. When we were done I asked for the check and as the waitress took my card and walked away, I told Candy she now had a decision to make, massage or no massage.
She gave me a little smile as the waitress brought back my card. I signed the receipt and I started to get up and we walked out of the restaurant. I let her walk in front of me this time. If by chance I wasn’t going to get another chance, I was at least going to get a good view of what I was missing out on. She had a greatly formed ass. If you could ever imagine a heart shaped ass, this was it. We got into the car and we drove the opposite direction we had come. I had a good idea where we were going. We pulled up to an apartment complex that I didn’t recognize.
“I guess you’ll be getting that massage,” I said.
“And maybe you will too.”
We walked into her little two story apartment and headed up to her room. She immediately lied down on her bed, face down, putting her arms under her head and gave me the go ahead to start. I mounted her from behind, getting right on top of her ass, and began digging my hands into her shoulders. She moaned lightly and told me to start working on her back.
“You might want to take you shirt off. I wouldn’t want to get lotion all over it.” I said.
She sat up momentarily and slipped off her shirt while I grabbed the lotion. I poured some into my hands and started to work it into her back, rubbing it in deeply. I had not lied when I told her I was good at giving massages. For whatever reason, my friends gave me a lot of practice. If someone had a sore back, neck or shoulders, it was always me that they came to. I knew what I was doing by now. I pressed the heel of my hand and thumbs up along her spine. She responded by groaning and moaning deeply as I kept working on her back. I unhooked the clasp of her bra to allow me unrestrained access to her back and continued working on her, really driving my fingers into her back.
“So do you want me to work on your legs?” I asked.
“Mmmmm. Yes, that would be nice.”
“Ok, well, that like I’m trying anything on you, but you’re going to need to take your pants off.”
She shot me a coy smile and sat up away from me taking off her jeans. I was hoping to get a good look at those tits but I wouldn’t get it this time around. When she laid back on the bed, what I saw got me instantly hard. She was wearing a pair of lacey boy shorts, something else that drives me crazy. They were a soft pinky tone that contrasted nicely with her tanned complexion. There wasn’t a single tan line on this girl. I’m pretty sure she spent a decent amount of time in a tanning bed. I poured some more lotions into my hands and began working it into her thighs. I looked up between her legs and saw that her panties were wet at the crotch. I started working up her thighs and kept looking back between her legs. From where I was positioned, I had an unobstructed view.
“Such a shame I’m such a gentleman.” I said.
“Well, I’m in the perfect position to lots of things to you.”
“I’d hate to lose the excitement by just telling you.”
“Well then go for it, my good sir.”
I slide one of my hands in between her legs and started to rub her pussy through her panties. I was right. She was really wet already. I slid her panties to the side and started to work on her bare pussy. I worked my fingers up and down her slit, working lightly passed her engorged lips. I slid two fingers into her and started working them in and out of her as I rotated around in a circle. I pressed my thumb against her clit as I was now feverishly sawing my fingers in and out of her. She groaned deeply into the pillow she was laying on. She flipped over onto her back, sliding my fingers out of her. Reaching into the night stand next to her bed, she pulled out a condom. She beckoned me over with a sexy smile and by curling her finger.
Once I reached her, she began to undo my pants and slid them down along with my boxers and I pulled my shirt over my head. I kick my clothes away along with my shoes as she began stroking my already hard dick. She took the condom out of the wrapper and rolled it down over my shaft. Once she was satisfied with its placement, she took the tip into her mouth and started working her tongue around in while she kept stroking the shaft. She tongued the underside, clearly having done this many times, and started to caress my balls with her other hand. As good as she was, I was ready to fuck that sweet pussy she had. I pulled her away from my dick and slid her to the edge of the bed. I put her knees over my shoulders and lined my dick up with her pussy. I took it in hand and slid it up and down her pussy a few times, making sure to rub it across her clit as well. “Quit teasing me, baby. I want that dick.” She said.
I was more than happy to oblige. I placed it at her entrance and slowly slid in, surprised at how tight she was. It actually took a bit for me to stretch her out to where I could slide in and out in full strokes. I started getting into a nice steady rhythm, enjoying the sensation of how tight she was. I was in no hurry. I took my time taking long slow and deep strokes. I would plunge in at the last inch getting as deep as I could. She seemed to have a fairly deep canal. She pulled her knees down off of my shoulder and wrapped them around my waist, pulling into me, matching my thrusts. She pressed her hips down with every thrust in being sure I hit her g-spot and rocked them up every time I pulled back, getting my dick to rub up against her clit. I enjoyed the extra pressure on my dick. It almost made her feel tighter.
She started pulling me in with more urgency. I began to give her faster and harder thrusts. She responded with deeper moans, her sounds becoming almost animalistic. I reached back and pulled her legs from around my waist. I rolled her over on her side and place her legs together quickly sliding my dick back into her pussy. I started hammering away, pumping into her faster and harder with every thrust. I grabbed a handful of her ass and squeezed it tightly before lifting my hand and bringing it down across her firm cheeks giving her a nice little sting. I saw my hand print and repeated the process a couple more times. She responded by giving little yelps, obviously seeming to enjoy the slight sensation of pain. I took a firm hold of her ass again with both hands and worked on really drilling into her pussy. I felt her clamp down around my dick and her whole body started to shiver as she climaxed. I started to slow down but she urged me to keep fucking her.
Once she came down from her high, she told me to lay down on my back. She got down between my legs and sucked my dick for a little bit before getting a leg on either side of me and slowly sliding her pussy down onto my dick. Once she was all the way down, she started working her hips back and forth grinding her clit into my pelvis. I reached up and plaid with her tits, thumbing her nipples and giving them a good squeeze. She started to bounce up and down on me and I moved my hands down to her hips to drive her down on me even harder. Each time she came down, I would thrust up into her causing her to let out deep moans. I felt myself getting close as my balls seemed to boil over with my cum. I thrust up into her one last time and emptied out my balls into the condom. She felt me finish and got off of me, slowly withdrawing my dick from her well fucked pussy. She reached her hand around the base of my dick, sliding the condom off expertly not letting a single drop of cum drip from the condom. She tilted her head back and emptied the condom into her mouth then dropped her head down to my softening dick and licked it clean.
“I just love the taste of cum,” she said.
“And I love the way you taste.”
“Well, have another taste then.”
She laid on her back and spread her legs for me. I wasted no time in getting down and sliding my tongue into her awaiting pussy. I slid my tongue all the way in and started to swirl it around in circles as I slid it in and out of her. I pressed my thumb against her clit and she immediately began to shudder. I felt a warm spray across my face and was taken by surprise. I had never been with a squirter so this was new to me. When she finished cumming, she leaned up and saw the look of surprise on my face.
“I guess I should have mentioned that earlier,” she giggled.
“Would have been nice to know,” I laughed a little along with her.
“It’s been a while since I’ve gotten off that good. I wasn’t really expecting it.”
“Well I guess I did good then.”
“Sure did. Do you need a shower?”
“Yeah, that’d be nice.”
She went and got me a towel and took a quick shower and she swapped her sheets and cleaned up a bit. I got out of the shower and got dressed. I walked out to her balcony to smoke a cigarette and looked at a very familiar golf course behind her apartment complex. I looked around the area and noticed that this apartment complex was two fairways across from my friend’s apartment complex. She came out and offered to take me back. I told her not to worry about it, that I’d just walk and told her of my new discovery.
“Well, maybe you can drop in again before you leave,” she said as she winked.
“I guess I won the bet, so you do owe me a massage.”
“You may have turned me on a lot, but I’m not saying that massage was better than mine.”
“I think I should judge that.”
“Well, I’m not going to charge for starters. We’ll talk more if you come back over.”
We both laughed and shared some small talk as I finished smoking. I thanked her for having me over and she thanked me for dinner. I said my good bye and headed back over to Nicole’s apartment. I walked in and was greeted by her dumbass roommate and his friends that were still playing Halo 3. Luckily Nicole was back from work so I wouldn’t be driven completely insane by the redundant sounds.
“You smell like sex,” Nicole said. “Where did you go?”
“Well, I wasn’t getting any around here.”
We both just laughed and had a couple drinks and headed to bed. I had an early day the next morning with the next girl that replied and Nicole had work.
To be continued…
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