I've been seeing an escort for the past three years. I’m married, but live a very naughty and secretive life. My wife and I have been married for sixteen years, but we have a rather vanilla sex life. We have sex about three times a week, but it’s always the missionary position and that’s great, but I’m a bit more adventurous. I’m also a bisexual man and have had some fun with three Shemales on a few different occasions.

My name is Ian, and I’m in my forties and have brown hair, blue eyes, and I’m in excellent physical condition. I have a very high sex drive and love to have sex with women or with Shemales, and hopefully someday I shall have sex with another man. But, that has not happened as of yet.

For the past three years, when I’m traveling to Chicago, I've been masturbating with an escort named Taylor. She is 5’3” with auburn hair. She’s very petite and has a very nice body with a beautiful face. Her breasts are on the small side, however she has very big nipples. And when she touches her clit, it swells up really big. It’s really quite amazing. She’s a very smart girl and I enjoy being in her company.

We’ve never had sex, but when we get together we watch each other masturbate and do all sorts of other fun stuff together. I’ve only seen her eight times. She’s very fun, discrete, and she’s twenty-three years old. She really gets my blood pumping, and I love to spend time with her. I’m much older than her, and it makes me feel good being around such a young and lovely young woman.

In addition to meeting up with Taylor, for the past two years, I’ve been having a very interesting on-line relationship with a woman in Asia. Her name is Molly. We chat a lot and have a lot of interesting times together. We love to talk about our fantasies and any other sexual topics we like to talk about together. We have had cyber-sex and have masturbated together on Skype. I’m a serial masturbator and love to do it alone or with others.

A few months back, I started to explore women’s panties. I love all the different styles and fabrics. I also love to wrap the panties around my cock when I’m jerking off. The silk feels so nice against my skin. I also started to buy panties and would wear them under my street clothes. It really makes me very excited and I just love how my cock feels in the panties. I had shared this information with my on-line friend, Molly. Molly also knew about Taylor the escort that I had visited on few occasions.

While I was talking to Molly one evening on Skype, she suggested to me that the next time I was with Taylor she wanted us to have a tassel spinning contest. The loser would be spanked by the winner. She also thought it would be really interesting, if Taylor masturbated in the tub using the shower wand. Then as Taylor would be doing that, I would be masturbating and watching her. She also said it would be really cool if I would record the scene in the tub. She wanted to also enjoy it, when she masturbated.

I was very excited about the conversation that I had with Molly. The best thing was, I was scheduled to be traveling to Chicago for an upcoming business trip. The good news was that Taylor, my escort friend is located in Chicago. I had called her and scheduled a night to have a masturbating date with her. She was thrilled that I’d be in town. I think she really liked me and enjoyed our fun that we had when we were together.

Before leaving for Chicago, I'd gone shopping and bought these really top notch tassels and also bought a pair for Taylor too. I bought us matching silk panties. They were white with black polka dots and were bikini cut. I also practiced spinning my tassels. I watched lots of online videos and I don’t want to brag, but I got really good at it. I was really looking forward to my upcoming trip and all the fun that Taylor and I would have.

I headed out to Chicago and was there all week. I had scheduled my appointment with Taylor for my last day of my visit. My work week was very long and very intense and I definitely needed to have a little fun. I’m a finance director at a manufacturing firm, and I travel a lot with my job.

Tonight was the night that I would be getting together with Taylor. Taylor was going to be meeting me at my hotel. I was practicing my tassel spinning a little before she came to my hotel.

I also was so horny with the idea of what would be happening, I needed to masturbate. I took off all my clothes, I went into my suit case grabbed my vibrating anal plug and put it into my ass. I then sat on the bed and played with my erect and very hard cock. I moved my hand up and down my hard dick. I held and massaged my smooth balls, while I stroked my cock first slow and then very fast.

I was imagining Taylor’s hot body and was getting myself all worked up. I was really jerking my cock faster and faster. Lightly squeezing at my balls. My pre-cum was oozing off the top of my mushroom head. I swirled my finger around it to take a taste.

“Oh God, this feels so fucking good. I’m going to come. Oh fuck!”

With that, I shot a huge load into the palm of my hand. I took a nice long lick at my come. I do love to do that sometimes. It tasted really good. I left the anal plug in my ass and got dressed. It would make me nice and horny for when Taylor finally comes to my hotel.

About an hour had passed and then I heard somebody knocking on my door.

Knock Knock

I looked out of the peep hole and it was Taylor. I opened the door to let her in.

“Hi Taylor, please come in.”

“Don’t you look very handsome?”

Taylor walked into my hotel room and we shared a hug and a passionate kiss. Our tongues danced in each other’s mouth. She looked really hot. She was wearing a red dress and red pumps.

I was getting really excited to start all our hot fun. Now, Taylor had no idea what Molly and I had discussed previously.

“I’m going to hop on my computer and get Molly on-line. We have a little game we want to play with you. Are you game?”

“That sounds wonderful. I’m so excited. What do you have planned?”

I went over to my computer and pulled up Skype so we could talk to Molly.

“Hi Molly, I have Taylor here with me. Molly this is Taylor.”

“Hi Molly nice to meet you,” Taylor said.

“Nice to meet you also. Okay, so Ian has brought nipple tassels and panties that you’ll both put on and you’ll both swing your tassels and the person that wins gets to spank the loser. Ian, will tape the results and I’ll decide on who wins. Does that sound like fun?”

“Yes, that sounds like a lot of fun. Will I get to practice a little? Since, I never did anything like this before.”

“Of course take a little time to practice and then we’ll get started.”

We both got undressed in front of each other. I got out the nipple tassels and we put them on each other and then we put on the matching white panties with the polka dots. Taylor looked so fucking hot.

Taylor then went into the mirror and started to practice. She looked so beautiful with her perky breasts. She really was very good at this. I didn’t want to tell her that.

Quickly, I knew she had a natural advantage with her perky breasts and big nipples. It was my job to record our tassel contest and email it to Molly. I got into position as Taylor was going to start our contest.

Taylor shook her breasts with the nipple tassels. She looked so fucking amazing in her cute panties and her breasts were just fucking so pert and perky with the tassels on. I was hard in my silk panties. I really loved the feeling of the silk against my hard cock. 

Taylor then videoed me doing the tassel spinning. I did okay, but was a bit jerky at times. After we were both done, I sent the video to Molly. We waited about ten minutes so Molly could review the tape and make her decision.

“Okay, guys the winner is Taylor. She won by a landslide.”

We both giggled when Molly announced the winner. I mean it was really no fucking surprise I knew she would win. I certainly wasn’t going to beat out a beautiful girl with amazing breasts and gorgeous nipples.

Since I lost the contest, I had to be spanked by Taylor. I had never officially been spanked by anybody ever. Taylor sat on the edge of the bed, I lowered my panties a bit and got across her lap. She proceeded to spank me five times on each buttock. Each time got harder when she did it. It was really fun and very exciting.

“That was so fucking amazing guys. Taylor, we’ve decided that you’re going to masturbate with the shower wand in the tub. Ian will record it, while he masturbates. Does that sound like fun to you?

“Yes, that sounds like a lot of hot fun. I’ve never done that before. I’m so excited to do this.”

“When you guys are done, ring me back on Skype. Have a great time you two."

Molly then logged off the computer and I shut my computer down for the evening. Taylor and myself then took off the tassels and our silk panties and moved into the bathroom. Taylor was so excited because she never used a shower wand to get off. Taylor then got into the tub and she sat in a squatting position with her legs spread. Her beautiful bald pussy was in complete view. She turned on the water and made sure it was warm. I stood over the tub recording her doing this. She then got started.

I had lubed up my cock, because while she was doing that I was going to be masturbating. I worked my hands up and down my six and a half inch cock. I jerked myself slowly and it felt so fucking good. Taylor looked so damn sexy in the tub.

Taylor then put the stream of water onto her pussy. Her clit immediately started to swell. I really got off watching her masturbate because her clit grew to an enormous size as the water hit it.

“I’m going to come. Oh fuck, here I come.”

Taylor was moaning as she came. She was completely lost in the pleasure of the water hitting her enormous clit. I was slowly, but firmly stroking my cock as I watched her have a series of orgasms. Her breathing was increasing, her moans and screams were getting louder and louder. Her grip on the shower wand was getting tighter and tighter. Her clit was dancing and growing to an enormous size. It was so fucking hot and very exciting to watch.

Taylor kept going until she couldn’t handle anymore. She started to laugh.

“Oh fuck, that was so fucking amazing. I’ve never thought of ever doing something like that ever before. When I leave here, I shall stop off at Home Depot to pick up a shower wand head.”

Taylor then proceeded to spray the spraying water on her amazing breasts. She fondled her erect and very huge nipples. Her breasts were so fucking hot to look at.

I was hovering over her stroking my cock as she watched me. She leaned a bit closer to me.

“I want you to come on my breasts. Come on Ian, do it! Come all over my breasts, baby!”

I was stroking my cock so fast now from the base to my head. My come exploded out of my huge mushroom head and first hit her beautiful perky breasts. She then swirled her fingers in my come and tasted it and then put her fingers back in my come and put her fingers into my mouth so I could taste it.

It was so fucking hot watching her masturbate in the tub, I don’t know how, but I was able to shoot the whole thing on video. My hand was very steady. I now use this recording on the evenings when I jerk off.

Taylor and I then showered together, and we just hung out and went back on the computer and pulled up Skype to talk with Molly again. I will never forget this night and often look back on the video when I masturbate.