Note: All characters in this story are 18+ years old.
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Jack can remember the 1970's with extreme clarity. High school kids were quite cruel, often deriding those who were a little bit different. Some were called "queers" or "faggots". Those that were offended would remain silent, lest the teasing would become more severe. He was fortunate not to be one of them, but the price was high: It was required that he join in with the cruel ones to be spared from their ridicule.
Not to say that he did not notice in the locker room showers. For he certainly did. There were short dicks, long dicks; thick ones, skinny ones; cut cocks and uncut cocks. Jack was, and still is, lucky to be in the last category. Then, nobody did any "manscaping". It was definitely a different time.
Jack had always considered himself as "straight", having been married for many years. However, over the last several months he had been having some bisexual urges. This could never have been discussed with his wife. She would never understand, so if he ever wanted to act on his feelings, it would have to be solo and on the "down low".
Jack is a 6'3", 190 #, average build male from southern US. He shaves clean, fully exposing 8" of manhood. Besides being bi-curious, he has another secret fetish: adoring the wearing of women's panties. His large collection includes bikini, boy shorts, tanga, thong and other styles. The cotton ones are not preferred. Instead, he opts for the ones that are silky, or microfiber, preferably with lace trim. He uses the smallest size that can stretch across his hips: for him, medium.
Opportunities are rare for donning sexy undies, but when it is possible, Jack tries to make the most of it. His becomes stiff almost immediately when stretching the silky soft cloth across his rod. Watching straight porn usually follows, with light rubbing through the material, then maybe using a bullet vibe. Within minutes he gets so hard that the panty crotch is stretched to the maximum.
Escape from the soft and lacy confines is inevitable. When the time arrives, his ejaculate is large, forceful and quite thick. Jack would hate to say this, but he almost prefers masturbating like this to actual sex. It is that good!
Upon surfing more porn, he came across videos of forced sissification. Men wore compelled to wear lingerie by their mistresses. It was kinda hot, but not what was craved. He found pics of cocks in panties and vids guys in lingerie whacking off, quite as he did. Getting very turned on, he finally stripped, put on his silky thong and did the dirty deed. The keyboard and screen of the pc were drenched with a hot load.
After the cleanup, he sat down in front of the computer and realized, "Now I know what I want to try: a mutual jackoff session in panties with another guy in panties! Fuck!" He was getting hard again, just thinking about it! "How far would it go? Would I rub the other guy's cock? Yes! Would I put my lips on it right through his panties? Oh, hell yes! Would I take it raw, right in my mouth? Maybe! Even more than that? Well, I don't know for sure, but I cannot wait to find out!" All these thoughts and more raced through his head.
The next step was to find someone reasonably close in distance; someone that he didn't know, but with similar interests. He found this local hookup site and made the post:
"Married older gentleman seeks like-minded male. Must have a love for wearing women's panties, porn and be able to host. Seeking mutual jack off session in panties. Touching and more is a definite possibility. Love of sports is a huge plus."
When he clicked the "post" button, it was only five minutes before the first response. Unfortunately, the guy acted like he didn't even read the words that were posted. He wanted a quick "hit it and get it", with no mention of anything that he was looking for. After a deluge of additional replies, finally one was received that met all criteria: lives close, loves wearing panties and loves sports.
The sports part was for three reasons. First, it would give an excuse to meet for a discrete j/o session. Secondly, it would give them something in common with each other. And lastly, they could watch the game after blowing their loads.
Emails were exchanged for several days. It was found out that Chris was an avid fan of Jack's favorite teams. The two shared face pics, body pics, and, of course, dick pics. Chris' cut 7.5" looked pretty good in his tight little green bikini panties! Finally a meeting was set up in a sports bar. They hit it off pretty well.
Parameters for a hot session were set: They would respect each other's boundaries, but let the situation dictate itself.