Later in the day, and returning from a drive into town, lunch, and a few other things, we then returned to Red's place.
Once inside, we checked our emails, surfed for a bit of porn. and then red suggested that we retire to her bedroom for another masturbation session.
As always, I was eager to head off to the bedroom for some more masturbation pleasure.
Once in her bedroom, Red then gave me the things that only you and I could see (that was the Wednesday February 2, 2011 entry), and it was 2 bras, and a pair of panties.
She told me that I had to try them on, so that she could see how they looked on me.
I could not believe what I heard cum out of Red's mouth!
In a flash, I had them in my hands, and was checking out the cup sizes.
The first one was a 36B, and once I put it on it was a bit tight around the chest, and my man tits almost fit into the cups. Lol
Red took some pictures of me checking out the cup size, as well as putting it on and modeling it for her.
This bra had a smooth cloth inner and outer shell,
It felt rather nice to wear, a bit snug, but still nice to wear, and will have to get Red to take some pictures of me wearing it next time we get together when she masturbates me.
The straps were adjusted pretty good, and once it was positioned I rather enjoyed the feel of it on me.
After a few minutes of wearing it and modeling it for Red, I removed the bra, and picked up the second one.
This bra was a smaller cup size, a 36A cup, and my man tits fit perfectly in the cups. Lol
Since the person that had worn the bra before Red got them had a much different body than I, and I know that it was a female, and of course she would have been built differently than my, but she was also smaller in frame.
Her tits would have been a lot higher up on her chest that mine, so Red had to adjust the straps by letting them out so as to let the bra fit me properly.
Once the straps were extended and the cups adjusted on my man tits, it fit very nicely, tithe but nicely fitting.
I really didn't care for this bra as much as the first one I tried on, as I didn't care for the rough outer shell on the cups, and it was a bit too tight to enjoy wearing, other than a short time while I was masturbating, or if Red was masturbating me.
Next I took the pair of panties, and tried them on.
Oh my, they felt so good next to my cock, and it felt nice on my ass as well.
They were snug fitting, but stretchy enough that if I wanted to reach inside and play with myself, there was enough stretch, and some to spare.
Again, red took some more pictures of me checking out the cup size, as well as putting on both the bra and panties and modeling them for her.
Since she is about the only female to see me wearing bras and panties, it was a real turn on for me.
Because I didn't want the panties to get soiled from Red masturbating me and possibly getting KY or cum all over them, I removed them so that Red had unrestricted access to my cock when it was time for her to play with me again, which was in a few minutes of removing the panties.
Once the panties were off and placed aside, I hopped onto the bed where Red was patiently waiting for me.
Red was fully prepared, she had the cloth, spray water bottle to re wet the KY, and the tube of KY.
I got onto the bed, and laid down beside her in the usual head to toe position, where Red could lay back while masturbating me.
Red did not get undressed this time, as she just wanted me to enjoy the pleasure of her hand, and did not want to get naked, which was ok with me.
She then applied a portion of KY to my cock head and worked the lube all over the head and shaft of my hard cock.
Sliding her hand up and down on my cock felt so damn good, and Red kept on stroking me as I tried to relax a bit while she worked her magic, as well as talking to each other, and again, it was about sex, cross dressing and masturbation.
Red played with my cock for about 15 minutes and tried several times to get me to cum, but it just was not going to happen.
I suggested that I straddle her hips and kneel over her and she could try that way to get me to cum.
She thought it was a good idea and I repositioned myself on top of her, straddling her hips, and giving her a different grip on my cock.
Once repositioned, Red took hold of my cock again, applied a bit more KY, and then began to stroke me a bit faster and with a bit more grip.
In this position, I could look down at her, and watch as her hand pounded away on my cock.
Red wastged no time at all, and before she knew it I was on the edge of cumming for the second time that afternoon.
Because Red had one hand on my cock, and the other holding my scrotum and applying some pressure on the base of my cock, she must have sensed that I was nearing ejaculation, because she gripped my cock a bit tighter, and brought me to orgasm and ejaculation.
It was not as intense as the first orgasm, and my load of cum was smaller, but then it had only been a few hours since I was last masturbated, and the small load of cum was expected, as well as a lesser intense orgasm.
After I ejaculated on the cloth Red had put over her clothes, I rested a minute to catch my breath, as Red cleaned up my cock and the cum from her hand.
Climbing off of Red and allowing her to get off the bed, I removed the bra I had on, and put it with the other one and the panties she had bought for me.
I told her that I really liked them, but asked if I could leave them with her for the ime, as I had nowhere to hide them at home right now.
She agreed, and I know next time I am over seeing her, she will have them ready for me to wear.
Red also told me that she would buy some more for me that were closer to my chest size, and that she would also se if she could find me some other items of womens clothing that i could wear when i am over visiting her overnioght, or when we go away for a weekend out of town together.
Checking out the cup size on the first bra Red bought for me.
Putting on the first bra.
Doing up the hooks.
Bra is on, positioned, and it feels quite nice to wear.
Removing the bra, so as to try on the second one Red bought for me.
Checking out the bra size, and it was a 36A, a bit tight, but my man tits fot in the cups nicely. Lol
Adjusting the straps, as they were a bit too short, and the bra did not fit properly once the straps were adjusted properly.
Getting ready to try the second bra on.
Doing the hooks up ....
Hooks fastened, bra adjusted, and it fits nicely, tight, but a nice fit ...... for my man tits.
Modeling the bra for Red.
Trying on the panties.
The panties fit very nicely, and were ever so comfortable to wear.
I was tempted to wear them for the rest of the day, they were that comfortable.
After looking at this picture, I realized that I am a very unattractive transvestite/cross dresser (and I look silly too, but that is just my opinion), but who cares really?
It feels good, it turns me on, and Red likes me wearing the bra and panties for both the pleasure ofseeing me wear them, as well as when she masturbates me, and that is all that counts.
Red stroking my cock for the second time today.
The ejaculation was not that large, and the orgasm not that intense, but it was still most enjoyable.
