Ride it cowgirl!

Every January I attend a business conference. One of the highlights of this conference is the opportunity for Hot Hotel Monkey Sex! T and I have had some great sex while away from home where we feel slightly less inhibited so I always look forward to that.

My last orgasm was before Christmas, so we joke that I have not cum since last year even though that was only a month ago and I have been denied in the past for as long as 3 months. Still, I was thinking that being at the hotel would be a great time for me to be allowed to release.

I had bought some underwear for T for Christmas and had at that time bought a six pack of cotton panties in a variety of pastel colors. I definitely bought them for me! I had it mind that for the week of the conference I would wear these “everyday” regular panties for the week and I did.

The first night at the hotel, we were tired and just relaxing on the bed when T got up and brought something to the bed. “Give me your foot”, she said. The week before she had put nail polish on my toenails. She now had a bottle of bright red polish which she put on my toes. Wow! I will certainly notice that every time that I look at my bare feet.

The next evening was the social event. We had a fairly short time to prep before hand and I was surprised that T told me to get out my whipping implements. I got out the small flogger, crop and quirt that I had brought. She told me to get naked and stand in front of the mirror, holding on to the closet clothes pole. She then gave me a substantial whipping, front and back. When she started using the crop she commented on how loud it was. I don't know if someone who was not into kink would recognize the sound, but she kept up a steady whipping as people were walking and talking in the corridor just outside our door. She would not have done that in the past and I marveled at the progress she has made.

I dressed for the dinner in a garter belt that has an attached crotchless g-string and thigh high stockings.

The dinner was uneventful until I went to the bathroom and T walked with me to the men's room. She stopped and told me that I was to go pee like a woman. No use of the urinal and she told me that since it was a strange toilet, I was not to sit like usual, but I should lift the seat and squat over the bowl.

This was a very new experience for me, made a little more difficult when you have to hold your penis down to point into the bowl. Nobody would know what I was doing in the booth, but I was still embarrassed. To top it off, one of my garters popped loose from the stocking and I had to struggle to re-attach it.

After dinner, we hurried back to the room. We undressed, well I kept on my lingerie, then made out for a short time until T told me to bend over the bed and she whipped my ass again. She was really hoping, as I was, that there would be some lasting marks to remember this by for a few days. Alas, there were only a few bruised dots from the knot on the quirt.

She then put a Chinese rope handcuffs on my wrists and tied my ankles and knees together and had me lay on my back on the bed. She teased my cock erect and rode my cock with her pussy for a few minutes. Then she told me to go get the strap on for her. I helped her put it on, then went down on her cock, sucking and licking it, only wishing that she could feel what I was doing for her cock.

I got her Hitachi magic wand then and she used it to give herself an incredibly squirting orgasm as she hosed down my leg. Then she asked if I wanted the strap on and I began rubbing it on my ass. I was soon very eager to have it in me, trying to shove it in without any lube. She had me get some lube though and lubed up her hard cock. I worked it into my boy pussy, a little difficult at first, but after a bit of fucking, I was riding that cock like a cowgirl. I fucked it hard and deep as she played the magic wand vibrator on the sensitive tip of my hard clit. I was delirious with pleasure and thought sure she would make me cum. Although she brought me to the edge several times, she had decided that she was not going to let me cum that night. Eventually she told me that she was tired and it was time to stop. I obediently pulled that long cock out of my man pussy. I removed the harness from her and cleaned everything up. Then I thanked her and we snuggled to sleep.

Yes, Hot Hotel Monkey Sex!

Pretty toes, shaved legs and bound whipping.

Since T shaved me from nipples to toes last fall, I have kept myself shaved entirely. We knew that I had a doctor appointment coming up in January and there was some mention of letting my hair grow.

T did not tell me to stop shaving and I felt that I was up to being exposed to a medical professional when my legs were hairless. They would not see that my pubic hair was also completely cleaned off.

As expected, there was no indication that anything was amiss during the exam, even when the practitioner pulled the waistband of my jockey briefs down to see a little more below the waist.

T had mentioned the week before that maybe we could paint my toenails after the doctor visit, as that would be a bit much to reveal. We have never done this before. That evening she brought a container of nail polish in the room and told me to take off my socks. She rarely uses nail polish and the only color she has is very modest, a brownish red. She painted my toenails, which to me was embarrassing due to the nasty condition of my toe nails after years of rough outdoor work with heavy boots on.

Nonetheless, I was very happy that she did this to me and it was all her idea! Maybe next time we can get some bright red or sissy pink.

The following weekend, she mentioned that now that my doctor appointment was past, it would be okay to leave marks on me. I said, yes please! She gave me a quick whipping with the riding crop that left red stripes but unfortunately did not last long.

The next morning I told her that I had been dreaming of being bound to the bed and whipped. I was surprised that she told me to pull out the underbed restraints and get out the flogger. I did so and left the handle of the new quirt that I bought recently sticking out from under the mattress where she had to notice it. She did not know that I had bought this. I was looking for something more harsh that would leave marks.

T fastened my wrists and ankles so I was spread eagle on the bed, bottom up, cock and balls pulled down in view and access.

She started with the flogger, warming me up well, then switched to a small flogger, which is quite stingy. The flogger was used from my neck to knees, including my cock and balls.

She then tickled my ass crack with something that I realized was the tassels on the end of the quirt. She really enjoys tickling and teasing me much more than whipping and hurting me. After getting her kicks out of tormenting me, she did give me a good whipping with the quirt. Not quite enough, unfortunately to leave any lasting marks, but satisfying. She then got out her magic wand vibrator and drove me crazy using it on my sensitive cock head and grinding it against my ass hole. She brought me to a writhing edge of orgasm and left me denied. I don't expect to have a chance to cum until maybe next week when we are at a hotel for a few nights.

T then released me and had me give her a fucking for the short time that I was able to do without cuming. My poor sissy cock can't give her a good fucking now since she keeps me under orgasm control. I love it!

She soon replaced me with the vibrator and brought herself to an orgasm.

New Year chastity

Happy New Year!
Although we did not accomplish what I had hoped for this year, that being renewing our wedding vows for our 30th anniversary with a FLR twist, it was a good year for gradual advancement.
T is feeling more confident and more accepting of things that used to be out of the picture.  She is more skilled and willing to whip me and her control of my orgasms (very rare) is common.
She has gone from acceptance to occasionally enabling my cross dressing and feminization.

This weekend, after taking advantage of my morning wood for some intercourse, T actually said that she wanted to have me wear the chastity device.  I was very surprised since she had little interest in it when I first bought one. I put it on and offered her the lock. She still thinks it is fairly ridiculous, too much effort and that I have a screw loose, but she did lock it. I wore it all day while doing some fairly physical work. I also requested that she put my leather collar on my neck.  I then slaved for her all day.
That evening she unlocked it and took the device off even though I would have been willing to wear it all night. She asked if I was okay to wear it the next day, of course I was.
This morning, she had to work and I had the day off, so I slept in and we did not put the chastity device on me before she left. She only worked half a day and we did some more heavy house work (digging and carrying buckets of dirt).  After that we showered before I made dinner. I have two different devices and I put the other one on, or was struggling to get it on when she entered the room.
She remarked that she thought that I was crazy to put it on since I still had a sore spot from the previous day. "But this one fits differently", I reasoned, as I tried to squeeze my balls through the ring.
I got it on and offered her the lock. She snapped the lock on and tossed the keys in the box. "There's the keys if you have to get out while I am working this evening". I told her that if it wasn't the first full day wearing it I would request that she take the keys with her.
It is my idea to wear the device so she is certainly not worried or even concerned at all about whether I take it off my self.  I am already in a state of self control of masturbation and request that she not allow me to orgasm for extended periods so that I can serve her better. I also have learned that sex is better for me with fewer, much better orgasms.
I don't know if she will have me wear the chastity device again any time soon, but feel that her telling me to wear it this weekend is progress.
She also said that she would reward me for working so hard for her this weekend and mentioned that after my doctor appointment this week, perhaps we could paint my toe nails.  That sounds very exciting.  During intercourse this week, she was whispering fantasies to me and talked about going someplace for a week where I could spend the whole time dressed up female and paint my finger nails too.  Sometimes those fantasies eventually become a reality!
She also whispered about telling other women about me scrubbing her kitchen floor while naked on my hands and knees. That would be so humiliating, but incredibly exciting.  Her fantasy was about telling her best friend and then having her come over to see me at work. That is one of my hottest fantasies, being dominated by my wife and her friend.