Cruising Nat

By: MiamiMark

Click here and read the text in the yellow box for background to this story.

That Thursday after work I joined up with Nat at the Mall and she asked me to pick out an outfit for her to wear Friday night at the 'see if anyone will pick me up' event she's been asking to do. Not only was I already getting worked up about the possibilities, but this was killing me. The outfit ended up being fairly simple and appealing. It was a dark grey flared skirt about ½ way down to the knees and a halter top which really brought out her breasts. No stockings were needed but she did buy a new set of silky black panties and bra at Victoria's Secret… the perfect touch.

Friday night we got ready and went out pretty late to the Oyster House (pub/bar). It wasn't as packed as I thought it would be and the crowd was fairly tamed. After about an hour we ended up going to South Beach. As soon as we entered the first club we realized why there had been so much traffic … Spring Break was almost over and everyone was out having fun.

We hit a total of 3 clubs that night and nothing out of the ordinary happened. I think the possibility of something happening is sometimes just as exciting. She would go in alone to the clubs and then I would go in and find a corner … which was pretty crowded. I would watch her as guys would flirt and buy her drinks. She even got to dance at least a dozen times with different guys but no one really hit on her.

Towards the end of the night, this one group of guys spent plenty of time talking with her and I couldn't really see what was going on. It ended up that they were from FSU which is where she graduated from and they were in the medical program. So they hit it off pretty well.

When she was ready to leave around 3 am, they tried to convince her to stay but she was so exhausted. They asked her for her number and she gave them her cell phone. That was it …nothing else. She left and I followed and we had great sex that night by talking about all the guys and which ones she found hot and wished she would've been with.

We both thought about it a lot the next day and we both wanted to go out but had previous plans to have dinner with friends. In the middle of dinner she got a call and was talking when she looked at me and practically blushed. It was the guys from last night and they wanted her to go up to Ft. Lauderdale , where there hotel was, to go out and party with them on their last night. It really sucked but we couldn't make it.

So that was the weekend plans, nothing out of the ordinary but still pretty exciting in its own way. She was being adventurous and I was getting excited .

About a week later the same guy, Chris, had called her from college and that went on for about 3 weeks almost every night. He would call and they would chat about b.s. things and after a while the conversations would get more and more sexual. I would lie next to her in bed and listen to her and him. After a few days of flirting they began to basically have phone sex and I would go down on her and play with her as they talked. She even had him on speaker phone at one point so I could here the whole thing. I'm not sure who was turned on more … her by him, or me by her being so turned on.

I finally came out and asked her if she wanted to be with him if she could and she never really answered me, so I told her she would have to tell me and plead to do it if she ever did want to. We left it at that.

A couple of weeks later she started asking him about the things he had done, the girls, the most memorable experiences, the kinkiest, etc. I'm pretty sure most of what he said was shit, but she loved hearing it and asking him to tell her all the details. It happens that he has an on-and-off girlfriend that he himself had shared with both his roommates. This started my mind racing but I kept my composure and said nothing.

Well, 2 weeks ago I was on a trip to visit some friends in Chicago and when I came back she asked me during sex that she really wanted to be fucked by Chris and then she begged me as she was on top of me. What could I say .. lol. Then I found out why she asked me. That weekend him and a group of friends were coming down to Naples (about 2 hours on the opposite coast) and renting a few condos for the weekend and he wanted her to go.

She had sort of already told him she would go and I was slightly shocked. I know she realized it because she quickly jumped in with, 'but I can just tell him something came up'. Of course I wanted this to happen. She was young and not too long away from the college environment of young men … and I wanted to see her in that world.

She had told him that the only catch was that her cousin (me) was also coming into town and she couldn't leave me behind. - she was pretty good, huh?

That weekend we took off and got there before anyone. We had also rented a room and I made sure we would all be on the same floor.

Nat brought every possible outfit you can imagine and half the bathroom in makeup and perfumes. She pretended to be casual but it was obvious she was excited about the whole thing.

By the time they all got there, we were already in the pool after spending the afternoon on the beach. They came down in small groups and we met them all. It wasn't long before Chris found his comfort zone and started talking and flirting with Nat. The whole time I had to pretend I was her cousin and look disinterested … which wasn't so hard with some of the girls they brought. I think there must have been a group of about 11 people, mostly guys but the few girls were amazing.

We had dinner out that night and then everyone went to a few bars in the area. It ended up being pretty much Nat, Chris, Hadj, Gus, and Gus's girlfriend in one group and I found myself in the other group. I think I tried to be fairly distant and it turned out to backfire, but I didn't care. It was probably easier to watch from another table or across the room than to be next to her and stare.

There was some hand holding and touching but nothing special to make note of. We finally got back around 3 am and everyone was pretty tired and we all split. Nat said he gave her a kiss in the hallway before splitting up. After that she was a wild woman in bed and all I did was flame the fire by telling her scenarios and asking her questions while we had sex that night. That is probably my favorite part … the talking about it.

Saturday everyone spent the day at the beach. I felt like the group chaperon since I was the oldest by quite few years. Nat, Chris, and their group spent most of the time together in the water, by the pool, having lunch … etc. I had missed it but Nat says they were in the ocean and he kept pulling her against him as he rubbed his hard on into her … all the time making out. I was in the room for part of the day since the sun and I don't mix too well (I'm pretty white) and had I known, our view from the room faced the beach. Should have brought binoculars … mental note for next time, hehehe.

As we got ready for dinner, Nat gave me a surprise blow job when she came in the shower. I could tell all of this was killing her. She kept asking if everything was ok and if I wanted to stop it. I kept assuring her that as long as she wanted to, I was more than ok.

We had dinner with everyone and then walked down the beach to some of the hotels to have drinks and move to the next one. Chris and Nat were all over each other with touching, kissing, etc. and so were Gus and his girl, and 2 other couples which hooked up that afternoon (or so I think since the girls weren't part of their group).

We ended up at their rooms which were enormous. It had one large shared area with couches, kitchen, etc. and then two very large rooms at either end. About 7 of them stayed there and the rest had another room.

At first, everyone was there and we all lounged around drinking beer and talking shit. Nat sat on his lap on the couch and his hands kept rubbing the sides of the legs. So here is the part you have to picture to get the scene. She had on a very tight jean skirt about 3 inches from her ass line. She couldn't part her legs throughout the night because the view would be immediate of her dark, dark, red panties. Her top was a black tight t-shirt without sleeves and if you stood above her you could see her matching lace bra all in red. His hands were rubbing her thighs and you could tell he would try to raise her skirt up and she would pull it back … flirting hard core.

We drank, we played pictionary (which I am still stunned about), and drank some more. The couples left to go elsewhere and by the end it was just about 6 of us. We were all pretty toasted from drinking and I could hardly keep my eyes open. Nat had actually fallen asleep next to him on the couch and Chris, Hajj, Gus, his girl, and some other guy were just talking about stupid things they had done so far in college. I sat on a big comfortable couch-chair and although I was trying to pretend I was passed out, I actually was exhausted and would lose consciousness and then wake up to hear them talking. I tried to stay awake hoping they would leave or do something but every time it was just stupid talk.

Finally Gus's girl was telling them she was going to bed and Gus went with her. The whole time I was slouched on the couch with my eyes closed but now my heart beat faster just thinking something was going to happen. One of their friends was completely passed out on the floor snoring like there was no tomorrow through this whole thing. Then I heard Hajj, then only guy who did not drink that night, tell Chris if he was going to take a shower incase he need to use the bathroom first and Chris told him to go ahead.

I kept trying to listen to every sound and imagining some amazing stuff happening until I heard Chris try to wake up Nat and tell her he was going to change and then to bed. She just moaned and said some things I couldn't make out … and I'm sure he couldn't either.

Well, as I laid there trying to wait and wait, I kept dozing off and on again. When I woke up one of the times I definitely heard Nat moaning. I couldn't turn around or Chris would notice so I just had to sit there and listen. He was eating her out right in the middle of the living room. The only thing I heard Nat saying was 'yeah .. mmmm … yeah' but you could tell in her voice she was still partially out of it.

Later she told me that she was dead asleep and woke up laying flat on the couch with Chris eating her out. Her panties were off, her skirt hiked up, one leg on the ground, and her his hand under her shirt. She kept trying to get really awake but she had so much beer it was hard for her, even with that going on, to be completely awake. Nat is a light drinker and, after a few beers, is gone till the next afternoon.

After a while (time distorted thanks to Budweiser), I heard Hajj say, 'What the fuck dude … how about a little warning next time'. He was laughing and I heard him saying something else as he walked back into the bedroom. It didn't seem to phase Nat because she was still moaning and Chris was still eating her out.

I couldn't hear the rest … with him whispering and my heart pounding in my ears. Chris sat her up and started to make out with her while fingering her and playing with her ass. She was upset because she couldn't enjoy it as much as she wanted to.

He stood up and took pulled her off the couch and tried to walk her to the bedroom and she remembers stopping by the door and making out for a while against the wall and him telling her she needed to lay down before she fell and her laughing at that.

By this time I could hear nothing but was terrified of turning around to face them. These were the longest moments of my life.

Nat remembers falling on his bed and having him go back down on her. Then she was on her stomach as he tried to untie her skirt and pull it off and then unbuckled her bra. He never actually took off the bra or removed her shirt other than having it all bunched up above her breasts because she woke up like that.

Sad to say that she didn't remember too much that night other than occasionally coming in and out of consciousness when he moved her or was pounding her hard.

On Sunday Nat spent most of the day with Chris and Hajj. She said the only thing that happened was an occasional kiss or grab but the opportunity never came up with all the friends around. We ended up leaving late afternoon and talked about everything on the way home. He had invited her to come up to visit him soon and it was something we use in our fantasies. We'll see if we decide to do it but for now this was great.

*** AFTER NOTE --- she did go up and visit Chris on two occasions a few weeks later. He would and still does call often to have phone sex.