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Gay/Bi Male Fantasies

Katecdpt said:
One of many fantasies I do have.
An older retired next door neighbor looses his wife to medical issues. On the anniversary of his wife's passing, he reluctantly, but finally decides to get rid of her things. He puts some of her clothes in trash bags and leaves them out in the alley. He plans on eventually getting rid of all of her things, but just isn't ready to let go of all of them.
I find them out in the alley and start going through the bags of clothes. It doesn't take me long to realize the gold mine I have discovered. I take all the bags inside to try everything on immediately.
Days later, I'm out presenting as a woman while shopping and see my widower next door neighbor. He sees me and comments on how great his wife's old dress looks on me. At first I'm apologetic about wearing his late wife's dress. He touches my shoulder and tells me there is no need to apologize and how his wife would have loved her old dresses being enjoyed by someone else. Unexpectedly, he leans in further and tells me if I want to come over this evening for dinner and look at all of clothes in the hopes I will find more of her clothes I would want.
He greets me at the door with a big smile and hug. He invites me in and he pours me some wine while we talk. It's clearly event to me he has been lonely and wanting some company since his wife passed. We talk over dinner and some more wine. As he is clearing the table, he tells me to go look in her closet and pick something else to model for him. I do as he asks.
I come back out wearing one of her floral knee length dresses. He starts to tear up a bit. I rush into give him a long comforting hug. As our hug ends, I start to pull away, but he takes my hand and pulls me back into him, but this time, our lips meet and we kiss. We both blush a bit, but he explains that I look so much like his departed wife when they were both younger and he couldn't help him self. We kiss some more and he tells me he would love it if I'd like to come over and pretend to be his wife more.
View attachment 2541285
The story continues.

Kate
Click to expand...
stunning
 
I had a massage yesterday at a local oriental massage business. I’ve been there a few times now and always received a happy ending. Yesterday was my second time with “Tina” who is a tall pretty girl. Tina recognized me from before and was a bit more playful thus time as she used her teeth to bite my ass cheeks and nipples during the massage. After the massage was over and I was getting dressed I noticed that Tina’s feet were huge for a girl. I didn’t see any other indications that she was male but I’m really curious to find out. Next massage I intend to ask her if she is my “special” girl. Depending on her response I will lead up to asking if she has anything “extra.” I don’t want to insult her or make her feel self conscious. Are there any suggestions on how I can approach this with her.
 
saintcero said:
I had a massage yesterday at a local oriental massage business. I’ve been there a few times now and always received a happy ending. Yesterday was my second time with “Tina” who is a tall pretty girl. Tina recognized me from before and was a bit more playful thus time as she used her teeth to bite my ass cheeks and nipples during the massage. After the massage was over and I was getting dressed I noticed that Tina’s feet were huge for a girl. I didn’t see any other indications that she was male but I’m really curious to find out. Next massage I intend to ask her if she is my “special” girl. Depending on her response I will lead up to asking if she has anything “extra.” I don’t want to insult her or make her feel self conscious. Are there any suggestions on how I can approach this with her.
Click to expand...
As she massages you, let your hands wander. If you’re face down, rub her leg or ass. Read how receptive she is. On the flip, you might want to rub her front or have her straddle your face while clothed and grind her pussy (cock?) on your mouth…
 
Last edited:
saintcero said:
I had a massage yesterday at a local oriental massage business. I’ve been there a few times now and always received a happy ending. Yesterday was my second time with “Tina” who is a tall pretty girl. Tina recognized me from before and was a bit more playful thus time as she used her teeth to bite my ass cheeks and nipples during the massage. After the massage was over and I was getting dressed I noticed that Tina’s feet were huge for a girl. I didn’t see any other indications that she was male but I’m really curious to find out. Next massage I intend to ask her if she is my “special” girl. Depending on her response I will lead up to asking if she has anything “extra.” I don’t want to insult her or make her feel self conscious. Are there any suggestions on how I can approach this with her.
Click to expand...
I had a massage from a guy who did happy endings. Before the second time I asked whether it was OK for me to touch him as well. That was OK. "Free hands", he called it. After the main massage, I started to touch his legs, ass, and cock over the shorts he wore, which he then took off so I could also touch his cock, which got hard. It was the first (grown-up) cock I touched and it felt great. Better even was that I got him hard, I loved that. Nothing happened other than the happy ending though, we jerked each others cocks until I came. (He said beforehand he would not cum.)

So, you could ask if "free hands" are allowed...
 
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