Another first
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Posted:May 5, 2022 6:54 pm
Last Updated:May 14, 2024 2:45 pm 1997 Views
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On my way home, in a motel in PA. Not many people, outside entrance, and an idea.
For the first time, I went outside dressed in woman's clothing, with my wig and makeup. I doubt anybody saw me, but just the idea of it is a first for me. I need to work on a femme voice so if I do it again and somebody walks up, I can talk in a proper female voice.
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Success
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Posted:May 3, 2022 3:06 pm
Last Updated:May 14, 2024 2:45 pm 2083 Views
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For any people following my trip saga, Chicago is wonderful for its many resources. I put in a search, found an ad, and met with the person today. Much of my curiosity is now settled. I could stop. I may stop. There is small thing left that was left unfulfilled, but I had enough to know now.
What's it like? It's not like a woman would feel it, but it was interesting having a real cock and not a cold, stiff dildo.
Would I do it again? Yes, I would if the opportunity came .
more nights in Chicago, then a night outside Pittsburgh. Once I get home, I'll have to see what might work out.
Anyway, it was fun finding out, even if all my years on Alt really played no part in it.
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Chicago
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Posted:May 1, 2022 8:07 pm
Last Updated:May 14, 2024 2:45 pm 2097 Views
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Nothing much for the day. I drove here wearing bra, panties, and stockings under my t-shirt and jeans. I'm gaining an appreciation for women and issues with bras moving around. It might be better if I had boobs to hold it in place more, but I think they just move a anyway.
Nothing new on the fantasy/wish list. I'm considering trying some of the TS sites online, or maybe getting out to a bar tomorrow and see what happens. I do enjoy being able to wear dresses or skirts, but will likely do that in private. I don't have a femme voice and would never pass for a (or possibly even a gurl).
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Day 3, Omaha
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Posted:Apr 30, 2022 5:54 pm
Last Updated:May 14, 2024 2:45 pm 2170 Views
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Nothing yet, though I wasn't really expecting anything. Maybe Chicago will hold some opportunities, or maybe my fantasies will remain forever fantasies. The next few days will show.
Speaking of show, I wore panties and pantyhose all day today, the rest of my clothes. There was thing, though. I locked on a pink, plastic chastity cage this morning and almost hours later it is still on. I considered leaving the keys at home, but I want to be able to eat my cum on this trip. No keys, no cum.
It's really a minor thing, but I think I'll leave the curtain slightly open until I go to bed. Anytime I get and move around, there is the chance somebody might look in.
Tonight is the short wig, makeup, a more goth collar, summer dress, bra, panties, and stockings.
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Day 2, Omaha
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Posted:Apr 29, 2022 5:55 pm
Last Updated:Apr 29, 2022 5:58 pm 1932 Views
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It was a long drive, but now I'm sitting in a short dress, pantyhose, wig, and a bit of makeup. I'm feeling pretty good about things, though my fantasy is still out of reach. It's odd, but my nipples have gotten a lot more sensitive in the past half year. It must be the supplements I've taken. The boobs aren't any bigger, but they sure are sensitive. I'm not sure, but I think my underwire bras help push up just a little as well.
A bit of time to play online, then maybe some time playing in the room. I might even make some time later to broadcast and see what fish might bite.
Tomorrow is my second and final night in Omaha, then on to Chicago. It might be fun. I'm thinking I might wear a bra and go for a walk one morning while I'm there. I wore the panties and pantyhose while driving, and considered a chastity cage, but driving in a cage really puts pressure on my balls and I don't think 9 hours like that would be healthy. Not that I really need them any more, but it's best not to have to explain things to the doctor when it can be avoided.
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The journey
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Posted:Apr 28, 2022 6:58 pm
Last Updated:May 14, 2024 2:45 pm 2124 Views
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My trip has begun and I am on my own for a week, at least in the evenings. I'm sitting now in makeup, skirt, panties, bra, and top, earrings dangling and reminding me they're on. I had to take them off for a while to go out to my car. I'm still not ready to show myself like this to the world in general.
Maybe somehow on this trip there will be some kind of contact. I was going to broadcast, but the internet here is so bad I doubt it would work. Maybe tomorrow. I know it will work while I'm in Chicago. I will do a good motel there.
I'm still watching trans/sissy porn and wondering. Maybe it would be one and done, or maybe it would open up a whole new interest for me. It's impossible to know without cum shooting into my mouth. I've tasted a full flow from a woman. It might be fun to compare Sadly, conditions have made it so I don't really shoot anymore, and the flow is very reduced anyway.
Oh well, perhaps a new adventure tomorrow. Some time on this trip I want to step out of my room and walk around a little in the real world. Will I have the courage to try?
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Planning a trip
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Posted:Apr 6, 2022 7:48 am
Last Updated:May 14, 2024 2:45 pm 2301 Views
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From the end of April into May 2022, I will be traveling alone. I plan to bring a bag of toys and clothes with me and hope to have time each evening to dress up and play a little, possibly get online and broadcast.
It would be wonderful if I can fulfill some fantasies on this trip. I hope to at minimum step outside dressed femme in full makeup. I hope my nerves can handle it. I'm 6-3 and do not have a very slim shape, so I might be an obvious guy in a dress.
I think the wildest thing that could happen would be to actually meet somebody. I have a month to work on flexibility, a femme voice, and walks. I see videos and think, Could I do that? Could I walk that way, or sound like that? It's an interesting mental exercise.
My 3 nights in Chicago may be the most conservative. I'll be right among the buildings of the near north side. My other overnights will be in more suburban to rural areas, but I don't know anything about the culture there. Those stops will be in Indiana, Nebraska, and Pennsylvania.
One thing I do know I plan to keep myself caged most of the time when I'm not driving. I just can't imagine having the tightness down there and still being able to focus on traffic. I'm getting excited about my April 28 departure date already.
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Enjoying while I can
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Posted:Mar 30, 2022 11:03 am
Last Updated:May 14, 2024 2:45 pm 2234 Views
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And on it goes. Almost every day I try to spend a few hours in women's clothes, and if not the outer clothes at least panties. The weather is warming, but bras and women's tops will be more obvious. I'm not quite ready to cross the line to public, especially in an area where people know me. I do have a trip planned in about a month and hope to do at least one walk outside in makeup, clothes, and maybe a wig.
I'm also wearing chastity almost every day. I have 4 cages. Two are pretty flat and leave interesting marks when they come off. One is a pretty short metal cage with optional catheter that I sometimes wear. The other is a pretty standard pink tube. It's my favorite, probably because it points me down and I can sit on the toilet and pee hands free. Just one more mental step.
As for the clothes and public, I don't exactly hide in my house. I open blinds, but few people live directly across from me. It's the anonymity of probabilities. I can be seen from outside, but somebody needs to be looking at the right time.
I almost managed to make a contact, but the timing is a problem. If I were alone ... but I am not and there is zero chance my wife would approve. She will retire in a few months, so my window of expression is about to fall shut. I'm not sure what my future will be after that.
Meanwhile, I guess I'll keep trying to think of how I'm going to get up the courage to go out in public, and just how public that will be. A motel parking lot is fairly easy, but I need to work on my makeup skills. It would be great if I could find a woman to help me with that, but, again, small window of opportunities.
Back to the original questions. What does a cock taste like? What does it feel like in the mouth? How does the cum taste, and how does it feel to have a man shoot into my mouth? How would it feel on my face? Maybe I will get the chance to find out, maybe not, but the questions will remain unless I can get them answered.
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How did this happen? Confusion.
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Posted:Nov 9, 2021 6:44 am
Last Updated:Apr 6, 2022 1:37 pm 3968 Views
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I'm a father, had a good sexual relationship with my wife (and a few other women, though I shouldn't have done that), and now I find myself caught in the sissy trap. Does sissy hypno work? I don't know, but I do know if you immerse yourself in something it can start taking over how you think. Cum a few times watching sissy hypno and, well, that just reinforces things in a whole different way.
So here I am, not young, going back to something from when I was still in grade school. What is it like to dress like a woman? Not in slacks and a button top. I can do that any time. I mean, what's it like to have that open bottom on a dress or skirt? How does it feel to have the hem barely cover my ass? How pretty can I make myself? And back to "Why do I want to do this?"
I have a couple of dresses, some skirts and tops, and even some feminine sleepwear that I can only use when I take a trip alone. That option will likely end in 2022 when my wife retires. Of course, there is also panties, bras, stockings and pantyhose, and a few waist cinching garments. I need to trim my waist, and my arms are too big for anything except very loose sleeves. I've even shaved off my beard and let my hair grow longer so I can get in a little more experimentation. I'm not a real hairy guy, so at least there's no shaving my legs every week.
And then there's the other stuff. I have breast forms to add a bit of weight and shape. I have dildos. Dedicated dildos for my ass, others for my mouth. My gag reflex used to be so bad I would make doctors angry. Now, on a good day I can take a dildo into my throat. There are cock cages. Metal, pink plastic, and a couple that are nearly no length at all. Cuffs and ropes and locks and gags have been part of my play since the beginning several decades ago.
Yet there is there are the couple of other steps that I haven't taken and wonder if I ever will. One is to actually step out of the house or a motel room dressed as a woman and wearing makeup. I definitely need more work on how to do my eyes. I wish there was a woman who could do me up and let me see if I have any hope of looking feminine. Also, I've never had a real cock in my mouth.
I can't say I've never tasted cum. I've tasted my own. Many times. I've actually gotten quite used to the taste. Age has taken a toll on quantity, though. But I wonder, what does a COCK taste like? I can't get mine to my mouth, so the answer requires some help. What does it feel like to have cum hit the back of the throat? To flow onto an extended tongue? To spray across a face? And the more I see this stuff on the sissy hypno, the more curious I become.
Like a lot of guys, it seems, I imagine a "forced bi" scenario where a Domme restrains me and then brings in another man when I have no choice but to accept. How would I respond if simply given the chance to suck a cock? I don't know. I love the taste of pussy, and really miss it (no sex in this marriage in a loonnnnggg time). Am I just missing sex so much I'm willing to try anything?
Even up until a few years ago, the thought of any kind of sex with a guy left me just "meh" with total lack of desire. Why did I even start watching that sissy stuff, and why do I now want to see what it's like to suck a cock?
If anybody is thinking "what about your ass." that's a maybe. Of course, if I am restrained, I can't do much to stop anything. Glory holes? I don't know if random is safe. Group sex? Not as a first go. I need to see if panic sets in should the opportunity ever come up.
To do, or not to do? That's not the question. The questions are why, and would I?
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He or She or Other?
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Posted:Mar 28, 2020 8:23 am
Last Updated:Mar 30, 2022 10:45 am 3269 Views
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When I was around 11 years old, I suddenly got a strange curiosity. What did it feel like to wear women's clothes? It wasn't that I wanted to be a girl, though of course there were those odd times when I thought, "what would it be like...?" It was just the sensual aspect of 1) wearing the 'wrong' clothes and 2) exploring something different. The bra I immediately knew was pointless, but on several occasions I would slip on a pair of my mother's panties and a skirt. The opening on the bottom of the skirt was so erotic, even though at that age I didn't have much knowledge of the options. This went on until the night i slept with one of my mother's skirts and in the morning she found it in the bed. I couldn't answer truthfully, so I made up something about being curious about making babies and decided that was too risky.
It took a few more years to get my interest in bondage up. I would guess I loved seeing girls bound, imagined being helpless myself, and just sort of crossed lines. Still, at that point every fantasy was boy on girl, or girl on boy. I was still learning.
Life has gone on for more decades now, I still feel very much like a guy, and I'm still rather curious about, "what is it like ...?" And so the evolution has come down to a more general curiosity, always tethered to a male outlook. But ... what is it like? I need to be discreet, have my time somewhat controlled by a wife, but there is a big world I've never experienced and don't even know if I would like. But still, there is the curiosity.
I don't consider myself a TV, because my female clothes are just for those sexy fantasy times I can find. I feel like a guy in woman's clothing, vulnerable, open to being forced and yet terrified that if I'm forced I won't like it. It's that panic attack feeling of, "what if I get into it, change my mind, but can't stop it?" That is why I avoid roller coasters. I just can't seem to turn off my imagination, though. And so I come to ALT, and post pictures and videos some people may not like, living just a tiny piece of my fantasy that is relatively safe.
Isn't it strange what a royal blue skirt can do to a person?
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