Fun By the Hotel Window

This is a true story of what happened with my girlfriend and I. A little background is in order to help set the situation that brought about the evenings activities. She is 56, 130 lbs 5’6” with short auburn hair, hazel/brown eyes and her chest measures 36D. I am 40, 160 lbs 5’8 with short brown hair, brown eyes.

A few months prior to this evening I had assumed a fictitious name online and began chatting with her as this person. He was someone local to the area and over the course of chatting I would use innuendo and other techniques that drew her into my plan. As myself I knew that she liked well endowed as well as well off and this man I made up fit the bell to a T. Over the course of chatting I made sure that I got her interest with my writings and even sent her a few pictures to help with my plan. That plan was to have her stay at a particular hotel and high enough as I said that I could see the top 2 floors from where I lived.

As it worked out with my writings and peeking her interest about me we arranged meetings, however each time I had to make excuses as to why I was not there. Each time worked well and she consistently bought the reasons for my not being there as this man she was chatting to. As me I even arranged to be where she was meeting him just to make it look like I had no idea. This worked out well as she told him all about it and this time it was her reason for not being there. She even told him that I would have not understood, so I knew that she had some interest other then just meeting him as some of his writings were erotic stories with him watching a lady friend as well as imaginary stories of him and her having a little fun.

So, this brings us to what he wrote her that brought about this evening at the hotel. He told her that a fantasy of his was to watch her through the window with a telescope and she would know that he was watching. He knew that a fantasy of hers was to be watched so they planned this together to happen. It all came into reality on that date and here is how it happened.

She and I took a room on the 2nd from the top floor and it was facing the direction that he had told her he lived. This supposed to be unknown to me so I kept silent. We dressed for the dance, quite normally as it was after where the show is to begin. She and I left for the dance and during a slow song near the end of the evening she told me she had planned something for the evening and I was to go into the room and take a place behind the curtains that were left open and be silent and watch. This is where I knew I was in for a treat. Watching her as she thought she was being watched by someone else.

I went up 1st and took position behind the curtains and awaited her arrival. I had no idea what she was going to do, or what she would change into but that was soon revealed to me. She came into the room and began turning on all the lights. Making sure the room was well lit before making her way to the window and opened the sheers so that her watcher that I was not supposed to know was there in her mind could see into the well lit room. That is when the show began.

“Hmmm, what is that I see across the way? Is that a telescope? It is. I think I have myself someone watching me from over there. Maybe I should have a little enjoyment with my watcher.”

With that, she stepped back about a foot in full view of the window and of me behind the curtains and she began to do a little strip tease. She was pretending that she had seen the man watching as they had arranged because he was far away but close enough that a telescope would be enough to see all. Slowly she removed her top and pants and was in front of the window caressing herself as she imagined his eyes watching her.

“Do you like what you are seeing” she said aloud as she touched and caressed over her bra and panties. Teasing her watcher with earnest.

I knew if there were really someone else watching her he would be as hard as I was watching her. She kept this up for a good 10 minutes before she said.

“Hmmm, maybe you would like to see something a little more exciting. As she removed her bra covering her breasts, pinching and tweaking her nipples to full erection then turning and walking over to the bathroom. She was in there for only a short time and came out wearing a long satin and sheer gown that had only a single tie between her breasts. Under which she wore a lace g-string with black stay-ups and high heels. This was something that I had bought her and here she was wearing it for what she thought was this other mans entertainment as well as hers performing for him.

She came back in front of the window and said “How do you like this outfit my watcher?”

She then paraded around in front of the window, resuming her self touching and teasing for her watcher.

“Focus in on me baby” she said as she stood closer to the window and untied the single bow between her breasts. Slowly she opened her gown, releasing her breasts and letting them be clearly seen if there were someone out there watching her.

“Mmm, I bet you are enjoying this. Watching my hands and fingers caressing my breasts and nipples getting them nice and hard for you. I bet you have you cock out and you are stroking its long hard shaft. Do you like seeing me pull on my nipples? Here, let me slip this gown off.” She said as she let the gown fall to the floor at her feet.

Standing there now in just the stockings, heels and g-string she really got into touching herself. Slipping a hand into her g-string and letting a couple fingers caress her lips and clit. Dipping them inside her, getting them wet before bringing them to her hard nipples and covering them with her juices.

“See how wet you are making me watching” she said. “See how wet my nipples are, I bet you would like to see this? This is where she lifted one breast then the other to lick her own juices from her nipples.

“OK sweetie, now I bet you would like to see something hotter” she said as she walked over to the bed and climbed up on it.

Looking out the window she seductively lowered her g-string and spread her legs apart. Standing there she now let her hands roam over herself caressing her breasts and making their way to her wetness between her legs. With one hand she spread her lips and the other she took 2 fingers and rubbed them against her clit and once they were wet she inserted them into herself.

“Mmm, you like seeing that baby? My fingers feel so good inside. I hope that you can see how wet I am” as she brought her fingers from inside her to her mouth and licked her juices from them.

“Do you like seeing me taste myself baby? Want to see more? I bet you would like me to use this?” She reached down and from under a pillow she brought out her 7” vibrator with clit stimulator and held it up. Showing it for her imaginary watcher that she thought was actually watching her without my knowledge.

It was fantastic watching her masturbate in the bed all the while thinking that she had someone else outside watching her. She had me in the room, but this she was doing was not purely for my enjoyment as I was supposed to think it was. This was for her. Her fantasy that she thought was coming through having this guy she chatted with watch her please herself with him watching. Me knowing this made it very arousing and I had myself out, stroking as I watched her masturbate for her imaginary watcher.

“Follow the toy baby.” She said as she brought it to her mouth and licked the head. Wetting it for him. Once wet she took it and with one hand she spread her lips wide and let the tip of the vibrator slowly pass between her swollen wet lips. Sliding it back and forth over herself getting it wet from her juices. Then turning it on while holding the clit stimulator on her clit. Letting out a soft moan that steadily grew louder as the vibrator massaged her clit.

“Want to see it inside baby” she called out. “Want to see how I would fuck your hard cock if you were here” she said as the head slowly she pushed inside herself. Slowly, inch-by-inch she inserted the vibrator until the clit stimulator was buried up to her clit. The feel of the latex cock inside her and the stimulator vibrating against her clit had her almost screaming. The fell of it was brining her close to orgasm and when she does cum she will have to hold the cock in her tightly as she bears down and would most definitely push it out while she cums.

She drops to her knees, straddling the cock inside her and takes a pillow from the bed and places it under her and lowers completely onto the vibrator. Using the pillow as the torso of her watcher as she rides it up and down.

“Like the way I ride and take you inside baby. Imagine my tight pussy swallowing your hard cock like it is doing this vibrator. Feel the pulse and my muscles clamping down trying to milk your hard cock. Mmm, it feels so good inside I am going to cum on it.” all this she was saying as she rode the vibrator.

I was pounding my cock, almost cuming myself as I watched her doing this for her watcher. I could tell she was really enjoying this. Her and I have had some enjoyable sex, even mutual masturbation and I was watching her now seemingly more excited then I have ever seen her. She must have really thought that this guy was watching her. Then out it came. With loud moans and screams she began to cum.

“Oh shit! Fuck my pussy hard! Ram that cock in me baby I want to feel your hard cock inside as I clamp down! Yes! Harder! Faster! She screamed as she fucked herself for him into a very strong orgasm. She was so hot from all this that like once before she had squirted, she squirted again all over the vibrator inside her. Soaking it with her juices.

I could not take anymore and I came out from behind the curtains and told her to come over by the window and do me. I positioned myself where she stood earlier. Where she thought her watcher would see her. Now he would be seeing her doing me for him, or so she thought. She was a little timid at first, trying to get me to come away but I stayed put. I said your fantasy is the possibility of being seen, come take that chance here like earlier. It worked and she came over and I positioned to that she would be seen. Her mouth on my cock would be easily seen from outside if there was really someone watching.

She used her tongue at first, licking over the shaft, head and balls. Wetting them with saliva before parting her lips over the head. Sucking the head in her mouth while stoking me. This was a fantastic blowjob. After all she was performing so had to make it look good for him sucking and pumping my cock in rhythm. Faster and harder bringing me closer to cumming myself. I held her off and told her I wanted to fuck her doggy style. I bent her over a chair in front of the window and entered her from behind. We were at a good angle. She could see out and out could see my cock fucking her from behind. Pumping her pussy like that I knew I would not last long. I fucked hard until I was close then pulled out and told her to face me close to the window where I took my cock in hand and jerked myself off on her face and breasts. Telling her to rub my juices in and to clean me off when I finished cumming. Then I started to shoot my load all over her face and breasts as she rubbed in my cum and cleaned me off in front of the window.

Once spent we moved over to the bed and turned off the lights and went to sleep. To this day I have never told her I was that guy she was chatting with and I expect never to tell her. I stopped doing that as I found out that she likes to do a lot of exciting things and there was no need to invent someone. We can do anything we like as our only limitation is our imagination.

She has however told me she fantasizes of getting a ride and she gives him a bit of a show. She has not gone into detail but if we do this I will be sure to write about it for everyone to enjoy.