Although I have never considered sexual interaction with another male, I have fucked my ass with a (big) wooden dildo, and know that the prostate massage (with a little help sometimes) will cause me to ejaculate.
A gay guy named Fred bought a house next door to where my wife and I have lived for several years, and he really is “pretty” but also masculine.
I suspect he would be up for interactions because he has flirted with me on occasion, but never any overt suggestion.
I came up with a device I thought would allow me to “ease into” gay sex without really having gay sex. I took an old pair of shorts, and cut open part of the bottom, starting just in front of my asshole. I stitched together a “sheath” about 18″ long, and big enough around to easily allow my wooden dildo (2.5″) and had a sort of “vulva” area- the fabric was felted waterproof.
I stitched this so that the vulva area showed between my legs, and the sheath would pass between my testicles and up along the shaft of my penis (inside the shorts). I lubed the whole thing up with KY jelly, bent over and slid my wooden dildo into it. It seemed to work great, and I added some strings to hold it in place, especially so my cock would get rubbed instead of moving away.
After removing the dildo, I put rubber bands around the sheath, all the way down to the vulva area, and (wearing these shorts) went over to neighbor Fred’s house.
I knocked on the door and nobody answered, but the door was open slightly so I went on in. Fred is a sort of strange guy, and had always claimed to have found an alien lifeform in the desert and that he took it in as a pet and fed it algae. I probably should have been more interested, but I had actually refused Fred’s offer to SEE this alien life form, which Fred said was unlike anything on Earth and had 6 short legs that also worked as arms.
When I entered the living room, I saw a sort of glass room in the corner, and when I looked inside, there was this blob with 6 legs. It either saw or sensed me, because it started to sort of hop up and down- apparently expecting something, maybe a meal. I could not find any food around, but did notice that each of the creature’s legs was about the size of the dildo I had designed, and I wondered if maybe it would be interested in fucking me, instead of Fred.
Of course, I probably should have consulted Fred before I tried this, so I was horny but reluctant to assume anything. What are cell phones for?
I phoned Fred, who was at work, and told him that I noticed his house door was open, and I closed it and was going to lock it, but thought I should call and find out if maybe someone is robbing the house.
Fred suggested calling the police, but I explained that it was already 30 minutes because I figured he had just rushed off on a short errand. Fred suggested I check to see if everything is OK inside- and lock the door behind me. He mentioned that his alien (whom he called Sarah) was very friendly and if I wanted to, I could play with him- but not to let him out of his glass corner. When I said maybe I should wait, he was certain that there was no need- and that Sarah loved to play catch, and there was a ball in his room.
So I returned to his room and opened the door, while Sarah came to the door to greet me, and soon appeared to be enjoying the handling I gave it. I sort of experimented with it while examining it, and I came to the conclusion that it was both male and female sex, because it had a special protuberance near one leg near the body and an opening on near another leg near the body. Plus it had a sort of mouth between the legs, much like an octopus- but it lacked any beak which can be formidable in an octopus.
I played ball with Sarah for a while, but it seemed to prefer being rubbed and otherwise handled. Eventually I squeezed the small protuberance and discovered that it swelled up quickly if I kept on playing with it- and Sarah really seemed to like it- if I stopped, Sarah immediately moved to get its bump (now the size of my thumb) into my hand.
While playing around with what I presumed was its cock, I took one finger and ran it around the edge of the hole I had noted- with dramatic results. The edges of the hole swelled up and a slippery mucus appeared, and Sarah started to be very agitated. I wondered why it didn’t just fuck itself, but apparently he had become accustomed to having Fred do that for him.
The hole looked small, but I don’t have a very big cock and by now it was stiff- thinking about this strange alien creature that looked to have a really nice hole to fuck. When I pulled out my erection, Sarah quickly turned and jumped on it and soon had managed to impale its hole on my cock. Didn’t take a genius to start fucking, which was exactly what Sarah expected, and I discovered that it’s hole could sort of “milk” my cock with rhythmic squeezing and peristalsis that was simply fantastic- maybe I should make a masturbation device that mimics it?
I didn’t know how to tell if Sarah had finished, but I soon found out because when I tried to pull out- I realized Sarah had clamped down on my cock, and since it was not uncomfortable, I didn’t worry. Soon the rhythmic squeezing actually had me stiff again, and I was fucking Sarah some more.
But before I came again, there was a sort of strange sensation and my cock was expelled, along with all my cum. Sarah was soon sucking it all up with her sort of carp-like mouth, and I realized that she considered this to be food of the finest order.
When Sarah finished, it came over to me and jumped up in my lap. I had moved my cock back in my pants, but Sarah was interested in getting me to play with its protuberance some more. I decided to suck it a little, and found that sucking produced even more agitation than fingering did, and the thing was growing larger and larger. Sarah knew what to do before I remembered the special sheath I had constructed to simulate getting ass-fucked, apparently Fred had been really getting his ass fucked, because Sarah clearly wanted access to my butt. I knelt next to the chair, but Sarah must have realized that the stupid sheath was NOT part of me. I tried to grab the now-banana-sized protuberance and put it in the sheath myself, but Sarah would resist and I didn’t want a fight.
Then I decided, what the hell, a banana won’t hurt- I have crapped out turds that are much bigger than THAT thing. So I dropped my pants, and in a flash Sarah had her protuberance in me and was sort of vibrating it. Even though I had just come, the vibrations on my prostate were magnificent, but I also noticed that the thing seemed to be getting a lot bigger. Pretty soon my rectum was totally full and my prostate both compressed and vibrated by this ridiculous penis-like organ. Then I felt a sort of whooshing, and the whole think slid out, along with about a quart of alien cum. I guess it had something that swelled up to keep it in, then it squirted out everything, and then it deflated and pulled out.
Sarah seemed happy, and was no slurping up its own cum, even though there was some of my crap along with it. I was amazed- and realized that this was more fun than I had had in the past month or year.
Next time I see Fred, I will have to find out how to get my own pet alien?