Wish I was still a cocksucking sissy fag
I was single for about 15 years between marriages and spent much of that time as a gay sissy cocksucker. This was in the late 80s, 90s, and early 00s. I stayed closeted, but ended up crossdressing quite a bit at home and sucked off a far amount of anonymous cock at adult theaters, ABS, and public restrooms. It was the best time of my life in spite of various other problems and I regret giving it up to get married again.
After easing into it after several years I was keeping my legs and body shaved and smooth on a regular basis, and keeping my toenails painted. I frequently wore panties, nylons and garters under my pants to work, and eventually even a chastity cage. I worried that some folks would see the outlines of some of these things through my pants and know I was a sissy, and this worried and excited me in equal parts.
At home after work I would strip down and wear nighties, lingerie, and high heels with the nylons and garters. After dinner I would almost always spend at least a couple of hours reading or watching porn, jacking off and edging and/or playing with big dildos and butt plugs, especially if I was still wearing my cage. I would usually sleep in a pink babydoll nightie, and was not very consistent about keeping the drapes closed.
The weekends were even better, and I spent at least half my time on closeted sissy sex play both saturday and sunday. This started with shaving and bathing, occasionally an enema, applying makeup (lots of makeup!) and fake nails, and a full en femme outfit including breast forms, wig, and jewelry. I had lingerie outfits in several colors, two maids uniforms, and several dresses and miniskirts. I would do my house chores like this and then settle down to a good 4-5 hours of sissy sex play.
Much of this involved training my boipussy to accept larger and larger dildos and butt plugs up to about 3.5 inches, often for several hours at a time. Anal play is absolutely heavenly, feeling as if you are always just on the edge an incredible orgasm just as long as you keep it up. Certainly the most intense and pleasurable sensations I have ever felt in this lifetime. Sissygasms were always hit or miss, but I would achieve one every month or so. Afterwards I would be so exhausted that I couldn't get up or even move to take out the butt plug for a good 15 or 30 minutes.
Once every 3 months I allowed myself to get fairly drunk on a six pack or a full bottle of wine. This made the anal play better, and I would always recyle a quart or so of the beer by pissing into a glass several times and drinking it.
Every other week or so the urge to go out and suck cock would build up hypnotically by mid afternoon, almost as if an external power was controlling my actions. So I would make plans to go out to an ABS, theater, or (later at night) a cruisy restroom. At first I would just wear lingerie under street clothes, but eventually had the courage to go out fully en femme after freshening up my outfit and makeup. A few times I even went out while still fairly drunk, but fortunately never had an accident or got pulled over. Once I actually drove through a late night checkpoint while sober wearing nothing but lacy white lingerie. I'm certain that the cops saw me, but somehow they didn't stop me.
At 6'2" I was never fully passable, but I am slender enough that I like to think I was pretty easy on the eyes. I was never really trying to pass completely, just make it clear that I was a sissy faggot cocksucker out to have fun with as many men as possible. Sometimes I would park a few blocks from my destination after dark and then walk to the theater or bookstore through the adult entertainment part of town. The exposure was very exciting and liberating.
There is no way of estimating how much time I've spent waiting to suck cock in booths, stalls, or the back row of theaters. It was just my calling in life to be available as a desirable and compliant cum dump for horny men requiring relief of their sexual tensions. Some days were a bit slow, and I would enjoy the video or grafitti while edging for a couple of hours before getting to suck off one or two cocks. Three or four was more typical. I would cheerfully suck off guys of all shapes, sizes, races and ages. I used condoms at first, but within a few years was addicted to swallowing down each and every load of hot sticky cum.
A few times things spiraled into a true oral gangbang with the right crowd and mood in the theater. Two of these occasions were when I was visibly drunk, which certainly made me more vunerable and submissive. I would end up kneeling in a corner, sucking one or two guys while a crowd of others watched and waited their turns. I would suck one cock after another, never seeing any of the feeders above their belts as each once finished off in my mouth and then stepeped away as another immediately took his place. I would lose track of time and the number of loads I had swallowed, but it was certainly at least 8 or 10 cocks over more than an hour on several occasions. These are the high points of my entire life, and I still remember them vividly after 15 or 20 years.
So I accomplished a fair amount in my time, even if I remarried out of a combination of work and family constaints, a long term illness, and general self doubt. This is all true except for very slight embellishment. I should not have remarried. More to the point, I should have started crossdressing and cocksucking full tine as a teen, instead of waiting until my mid thirties. I would have been much happier in life and made the world a better place. Do not hesitate to try cocksucking or crossdressing if you ever feel the urge to do so.