Red as always was open to my idea, and so the plan was put in place.
After telling wifey that my business was to start on the Friday morning, and I would be leaving on the Thursday evening so as to be at my business appointment on the Friday morning.
So, after work on Thursday, my bags were already packed and ready to go, I kissed wifey goodbye, and was off on my adventure.
In the early evening after dinner, I arrived at Reds place with bags in hand and ready to have a night of mutual masturbation, and intense pleasure.
Red greeted me at the door, and quickly pulled me inside out of the cold, and gave me a big bear hug and a big wet kiss on the cheek.
After taking my shoes and jacket off, we put my bags into her bedroom, and at one point I honestly thought that Red was going to pull me onto her bed, and take advantage of me, but she managed to control herself for a while, and let me find a place to put my things before going back out to her living room, where we talked and caught up on the latest in our lives since we last seen each other.
We talked for about an hour, about this and that before we pulled out my laptop computer and we looked at a few of the porn websites we both look at.
During our surfing, I began to reveal to her that I had a vast collection of naked women and short porno clips stored on my computer.
I told her that I had at that very moment, 4 gigs worth of porn that contain 13,130 images of naked women all sorted into various groups in 282 folders, and 1.9 gigs containing 521 short porno video clips.
As we looked at a few blogs that I follow, I told Red that I had this and that picture in my collection, and showed her the picture in my collection while accessing the site.
I told her how I grouped pictures together, and that each picture could be in more than one group, like a woman wearing a black bra with one big tit hanging out, had a shaved muff, and had her pussy lips spread open could be in 3 groups, one for wearing a bra one for showing a big tit or small tit, another group for having a clean shaven pussy, and another group for spreading her pussy lips, and could even be in a fourth group if she was showing her face and was very attractive, then she could be in a face grouping as well, and so on.
We also looked at several short video clips of various things, like women masturbating, sucking cocks, women masturbating men, women playing with their tits, bouncing tits, and so on.
Speaking for myself, looking at all the porn in front of Red sure made me horny.
I also told her of the time a couple of years back where I was in another city staying at a lady friends place while visiting that city on business.
This lady friend has a daughter who was in her early 30’s that lived in her basement suite and shared the cost of the house they shared.
Both of them worked, and many a day after they both went to work, I would make my way down to the daughters suite (which was open and was basically one of the bedrooms in the basement so there was no entering a separate suite or anything), and make my way into her room.
She had a dirty clothes hamper in her room, and I would look through her dirty laundry, and pull out some clothes of hers and try them on.
I would dress up in her bra, panties top and a dress or whatever else was in the hamper.
This really got me horny, and while dressed in her clothes, I would make my way back upstairs and log onto my laptop surf for porn and masturbate while wearing the daughter’s clothes.
There was many a time that I would have a pair of her panties over my head so as I could smell her pussy as I masturbated, and that was an ultimate turn on, but I never told Red that part.
Actually, there was a blog entry a few years back where I wrote about me taking one of her bra’s and a pair of her panties home with me, and posted some pictures of me with her panties over my head and wearing that bra, ( http://myblogonanist.blogspot.com/2007/02/monday-february-5.html ) and I also told Red that there are times when I go away out of town that I take that bra and panties with me and wear them and masturbate, and that I actually had them with me then and there.
I went to my laptop case and opened up a side pouch and pulled out the items to show her.
The daughter’s name is Kristen, and whenever I visit her mother in that city, I do see Kristen on occasion, and fondly remember wearing her clothes and masturbating in them with out her knowing.
By now, it was getting late, and we decided that it was time to get naked and hop onto her bed for some masturbation pleasure.
We turned off all the lights, TV, and whatever else was on then headed off to her bedroom where we both got naked.
As Red was on her bed, I took out my camera and started to take a few pictures of her as she was undressing.
As usual, Red really gets into me taking her picture, and posed for a few before I hopped onto her bed for some masturbation pleasure.
We talked more about my visit to Kristen’s place, and of me wearing a bra and panties while masturbating, and asked Red if it would be ok if I wore them tonight while we played.
Since Red knew from many years ago when we first started met and were actually fucking as well as her masturbating me that I liked to wear bra’s and panties while masturbating, and on many an occasion, Red would put her bra on me when she would masturbate me.
Red told me to go get the things I wanted to wear, and if I wanted to, I could wear the bra all night while we slept.
Hearing that, I was off the bed in a flash, got my computer bag and opened the side pocket with the underwear in it and took out the bra and went back into the bedroom.
Handing red the camera, I told her to take a few pictures of me with the bra both in my hands and wearing it.
Talk about a nice pleasant surprise on my part that she was open to me cross dressing once again.
Because I was so horny, and knew that if we were to mutually masturbate each other right then, that I would cum in no time at all, because when I am rubbing her clit and she nears one of her multiple orgasms, she would not be on control of her hand on my cock, and I did not want to cum so quickly tonight.
So, I told Red that I would play with her first and give her a bit of pleasure first before she could give me pleasure.
Red was open to this, and so I put a bit of KY onto my finger and worked it over her clit, making sure that it was well lubricated, and then began to rub her clit vigorously.
In no time at all, Red was having the first of at least 20 orgasms.
As I rubbed her clit, I could tell that she was getting close to cumming, as her clit would grow bigger and harder like a cock, and then she would start to quiver as she went into one orgasm after another.
It was a good 15 minutes of me rubbing her clit to multiple orgasms before Red told me that it was my turn to get off, and that she wanted to play with my cock.
We changed positions so that she was sitting on the bed, and I has laying in front of her on my back with my legs around her waist so that she had full access to my cock and balls.
Red applied a generous portion of KY onto my cock, and began to stroke my cock.
After only a few strokes, I was almost ready to cum, and told her that she had the control as to how soon she brought me to ejaculation, and that I wanted to enjoy some pleasure like the last time we were together, and she masturbated me for at least 30 minutes before she finally brought me off.
She agreed that she had the control, and would be careful so as not to bring me off to soon.
Stroking my cock for at least 25 minutes, my cock was more than ready to cum, as Red had brought me to the edge of cumming countless times, (I am sure it was at least 30 or 40 times) and she must have known that it was time to get me to ejaculate and finally have that long deserved orgasm.
Red stroked me slowly and tightly, as my cock pulsed, spewing forth a big load of hot cum all over my belly, and her hand.
While my cock was pulsing intensely and ejaculating, Red tried her best to squeeze and release the head of my cock, sending me into super intense orgasm.
Oh, it was so pleasurable, and it is too bad that it was over so quickly, because red just keeps getting better and better at masturbating me.
She let me rest a few moments so as to catch my breath before wiping the mess up with a cloth.
After we were all cleaned up, we were both exhausted, and climbed into bed under the covers, and turned off the light.
We cuddled and Red took hold of my cock as we wound down from a long and exhausting day, and I was still wearing Kristen’s bra and nothing else because I was too exhausted to take it off, and Red totally naked beside me and in no time, we were both fast asleep.
Here are the pictures that we took of each other....
I know that my man tits don't quite fill the cups, and I look like hell wearing it, and I really don't care because this moment is all about me!
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