I've been enjoying the posts here, the stories of folks journey from the discovery to the more salacious meetings, as well as the advice questions and also just getting to see different perspectives and get to deepen my understanding. Sorry this one will be kind of long.

I thought it might be interesting if I share a few of my stories from meetings or relationships I've had with Sissy/Femboy from the POV of the guys chasing or daddy (although I honestly don't really love being called that). I feel like it may be fun to read but may also provide some insights as I know a lot of questions come about how to host/entertain, meet or go from casual to LTR and so I feel like sharing some of my journey may help with this. If this is deemed inappropriate for this sub or wrong place, please let me know I will pull it down or modify it accordingly.

Quickly on me I am in my late 30's bi-racial man, I've always been very open-minded as a person and that applies to sex also, I think in my early years I was sometimes almost reckless/fearless that way, I found every/any opportunity to push the limits of my understanding and pleasure. So I've had many encounters with both sissies and trans women before but it was always random meetings through personals, apps, through escorts, kink clubs or other similar things, nothing ongoing.

Winter 2021 still pandemic while everything was shutting down early, I was working from home and feeling the doldrums hitting me hard I started browsing through apps & listings and ended up befriending a cute inexperienced sissy named Emily who lived in my city. Early on it was mostly just messaging, she's half Iranian and we bonded over being of mixed heritage, she'd send me pics and we'd chat, I learned she had been doing this on and off for a few years, every so often purging and deciding to go back to the straight guy life but for whatever reason it always ended up that way. She had finally moved out to an apartment without roommates and that had been the catalyst for this current bout of exploration.

Beyond some sexy snaps and light flirtations we got to know each other well on a personal level and chatted pretty regularly about anything and everything. I picked up that she couldn't really afford to do much shopping for outfits/make-up since since she's in uni full time and couldn't work much due to restrictions and closures and it was bumming her out because she'd felt she was making a lot of progress with her sissyfication. At first I half jokingly suggested she do onlyfans as I know friend's who've done it. "I'm not yet confident enough that I have what it takes to do OF and I'm afraid of family/friends finding out".

Finally a few days later I suggested "would you be comfortable with me picking up some outfits for you?", she had the cutest smile but tried to play it off, "Well I don't want you to think I'm fishing for gifts, plus I don't know how you'd get them to me". I came up with an easy plan of her setting up an Amazon wishlist she could share with me and that would allow her to keep her privacy if she wanted. While this isn't something I am in the habit of doing for like OF creators and people I don't know, it was fun to see which outfits and accessories she liked as well as those I suggested appear on the list. She would then tease me with snaps of her in different outfits or would model them during our chats, it was nothing major but I could tell it really helped her confidence and made her feel good and that was enough for me.

Toys would get added to the list as well and it was fun to facetime and see her please herself with them and tell her what to do with them "I'm so tight, I can only take the smallest toys in this set, please don't force me to put the bigger plug" Emily would say while putting on her best pouty but innocent face, she was so good at teasing and knew it would work me up. We'd talk about meeting up IRL but I never put any pressure for it to happen, "I'm afraid of meeting people not just for covid but also for security, plus I've never met another guy fully as sissy, only fooled around with friends a few times" she did start mentioning more often how horny I made her feel and how it was crazy how fast she would come if I talked dirty to her while she touched herself. "Even though I get that post nut shame about this and swear I am going to stop, I find myself dressing up like a slut for you the very next day you make me crazy".

Eventually we finally agreed on a date she wanted to come over and we went about planning the meeting, I inquired about what snacks she liked and and what she liked to drink, she asked me what outfit and wig I wanted her to wear, all the little details down to the perfume. She also had her rules, "I've never been out in public as a sissy but I don't want you to see me dressed as a boy either", "When I arrive I'll text you, you'll unlock your front door and wait for me in a different room, I'll go straight to the bathroom, shower and get dressed for you, so you only ever see me like that, same thing when I leave".

That Friday took forever to arrive, I was excited but also nervous, I was a touch worried things might go awry. I showered dressed casually, put a fresh towel and toiletries out for her, then the text finally arrived, I unlocked my front door and went to the living room which was within earshot but not in view. I heard her footsteps, the unzipping of her winter jacket, and her hanging it up (well at least a robber wouldn't hang up their jacket and take off their winter boots) I relaxed a bit. I heard her call out "hello" in her cute voice, "I won't be long" as she shut and lock the bathroom door. It felt like an eternity went by, the water for the shower going for a long time, I heard lots of movement and nervous laughter, I poured myself a whisky in the meantime, finally I heard light footsteps coming up the hallway "Hi cutie, sorry I took so long".

I turned around and there she was standing, she was taller than I expected, just slightly surpassing my 6ft, she was wearing a white short sleeved blouse and green woolen skirt combo with what looked like lacy patterned purple stockings. In her hand she was holding the end of a leather leash in my direction, my eyes followed the path of the leather lead & chain to where it was fastened to the leather collar around her neck that hard the word slut in pink letters, she had a mischievous grin on her face. The long dark straight wig she's chosen really suited her and framed her soft features, she'd really went all in doing her make-up so nicely. I walked up took the end of the leash, kissed her on both cheeks, "you look so sexy, in that outfit", I stepped back and pulled up the leash lightly and invited her to turn in place so I could see all of her. She had cute bracelets along her tanned slender arms, the mini skirt she had on really showed off her curves, I paid particular attention to her plump ass, the pics/vids did not do it justice, how does she hide such a juicy ass in her everyday life?? I'll never know.

I then lead her to the couch, sat down and then invited her to join me, she sat down next to me very close and then asked if she could take a sip from my whisky. We talked quietly, sharing a drink, I could sense that despite the bold intro she was very shy in person, eventually she asked quietly "I hope you're not too disappointed now that I'm here, do you find me cute?", "Of course, you are even hotter in person actually, I hope you're not disappointed at how I look?". "Oh no daddy, I told you already how handsome you are, I feel comfortable with you". I put my drink down, and pulled her in for a kiss, at first just slow and tentative and then more hungrily, we started making out furiously, I started caressing her legs, my hand slowly gliding and gently feeling her soft skin through the material, I then slipped my hand in her shirt, feeling that she had actually had something lacy underneath.I slowly caressed her nipple and I could feel her whole body shiver slightly and I felt her gasp, I pinched slightly, then again harder, she moaned, cocking her head back slightly and then pulled me back into a hard kiss, pushing her tongue into my mouth. We made out, and petted each other for what felt like an eternity I paused to check in if she was okay, "I'm alright, just nervous I've never done this before but I'm so turned on too", I looked down and sure enough there was her sissy cock poking up in the material of her skirt, I gently traced it with the tip of my finger over the material, I couldn't believe how full it was, I then hiked up her skirt lightly and it just came bouncing out, I grabbed it gently and gave her a playful tug, she gasped, "not yet, I know how sensitive it is" I said coyly.

We stood up and I slowly undressed her, it turns out she wasn't just wearing tights, it was a purple lacy crotch-less body suit that was underneath her outfit, it hugged her body so well, showing off her cute little belly and those juicy thighs. She saw me eyeing her "I've been keeping this one a surprise, I know you told me how sexy you find these". She then proceeded to undress me in turn and pushed me down on the couch so I was sitting and got down on her knees in front of me "I've been waiting so long for this, you better feed me daddy".

I pulled the leash to bring her closer till she was eye level with my cock, she grabbed it with one hand and slowly started rubbing it against her face and sniffing it, giving it little kisses in between "I can't believe I'm actually doing this", she then started licking it up and down. "spit on it, I like it messy" she obliged and all the while stroking my cock, licking, drooling on it and starting to take the head into her mouth. Her shyness soon gave way to excitement, she bobbed her head up and down faster moaning hungrily, while I'm not too big she did choke at one point while eagerly trying to deepthroat too quickly. She gasped and then started giggling "I guess it's not as easy as it looks in hypno videos" she had saliva and snot dripping down her face, yet she wasn't deterred and pushed on. She kept sucking my cock and moaning with such intensity encouraged by my panting and calls of "good girl, just like that" it wasn't long until I couldn't take it and told her I was going to come, Emily pulled me out of her mouth and milked my cock all over her face, all the while making eye contact whispering "more, more" with each stroke, barely flinching as each spurt of ropy cum landed on her face. She kept pumping my cock for what felt like an eternity flashing a devilish smile when I finally begged her to stop "you're killing me"...what a sight she was, her face glazed, her make-up ruined, a fake eyelash coming unglued in a corner. "You're my perfect little slut", I bent down and we kissed through the absolute mess of her face, it was so hot, she finally got up "let me go clean up and make myself pretty for you again".

We ended up having one of the more depraved but fun nights I've had with someone, we went slow at first but soon became more comfortable and brazen with each other. I feel like this post is already so long so I'll stick to highlights.

Taking a break watching some of her favorite sissy porn and working her through a set of 3 different sized butt-plugs (all moderate sized) so she could limber up, she always told me she was super tight but she wasn't kidding, whether it was nerves/resistance/natural I don't know. I went gently used lots of lube and she was having fun, she insisted on keeping the biggest one in while we kept playing so she could get used to the feeling. At one point she excused herself to use the bathroom and I heard her laughing, when I asked what was going on, "I can't pee, I'm so full back there it's making it difficult not to push it out" she kept laughing, I walked in the bathroom and she was standing there, shaking with laughter, until the plug popped out the other end and she finally able to relieve herself all the while chuckling.

Later on we were fucking standing up in front of the full length mirror in my bedroom, I was pulling the leash tight as to force her to watch herself be fucked, "look at the good little slut you've become, look at how much you're enjoying this", she was moaning and watching her sissy cock flopping around and dripping everywhere, "I'm such a slut, I'm a worthless slut" she started begging all the while to be allowed to touch herself. When I finally relented, I put my hand around her throat so she couldn't move away and whispered in her ear "You'll never be able to go back to anything else but this feeling, you're ruined, you're my little whore now". I felt her rise on her tip toes, felt her ass tighten around me and then her orgasm wrenching through her, screaming and jerking her cock with such intensity, until her knees gave out. We'd have collapsed if we weren't so close to the wall, I gently led her to the bed and we flopped into a sweaty dazed heap, with me just petting her hair and neck while she caught her breath.

Later sensing I was still excited Emily was insistent to make me come again, stating that she needed to surpass the orgasm I gave her...it got beastly. Since she has such nice feet, I oiled her feet and made her give me a footjob, the silky netted material of the stocking driving me nuts, Id' take turns sucking on one of her feet while jerking off onto the other and then I'd put them together, slipping my cock in between her arches, watching her caress her body while encouraging me, yet it wasn't quite enough to take me over the edge.

She then pushed me onto my back, climbed on top of me and slipped my cock into her ass violently, "wait I should get a condom!". She put her hand over my mouth to silence me and rode me like she was possessed, bucking her hips harder, the sound of her body slapping against mine loudly, she was grunting and moaning with every thrust. I'll never forget it, I lost my mind, she felt incredible, every inch of her burning hot and pulling me in deeper, it was like I was under a spell, her dark eyes staring into mine. I squeezed her soft ass with both my hands digging my fingers in hard as I started lifted my hips to meet hers, my moans muffled by her hand still over my mouth, after a few minutes I came hard, almost on the border of painful, my head spinning. She stayed on top of me a long time feeling my cock throbbing inside her now very sore ass, until it slipped out with a wet popping sound, releasing a stream of gooey cum behind it, we didn't say a word just stayed in the moment.In the end, she dozed off for a while while I spooned her, after she woke up we chatted, kissed until it was time for her to go. I got up told her I hoped I'd really see her again, went to the living room to let her shower and change, It was like the opening of the night but in reverse, with her finally calling goodnight from the entrance as she left, she texted me from her car "That was so hot, I'm your sissy slut from now on".

After that we saw each other pretty regularly for about 4-5 months, she even stay the weekend a couple of times, being able to be dolled up for 2-3 days straight, felt like she was at her happiest then. When her finals arrived it was more sporadic understandably but I think the stress of that combined with some family fights brought on a purge. I got a cryptic text one night thanking me for the times we spent together, that I would eventually find the right one for me but that she couldn't go on being a sissy that it felt wrong and then I lost all contact, emails, mobile all ceased working.

Since then every few months I will get an e-mail from her, always from a new email address, we will text and catch up. At first she would tell me she's done being sissy that she's not trans and so she shouldn't be doing that. She once even thanked me for teaching her so much that she uses my moves on girls with a lot of success which made me laugh. That didn't last though, because a few months after that she'd be sending me dirty snaps of her in outfits or would message asking me to talk dirty to her. If I do we have a hot session where she cums fast and hard as she always did and then she'll disappear again, I try not to encourage or push things, I know it's not easy, family/community/religious pressure along with all the confusing mess of figuring oneself among that. I've since had a few other LTR with sissies but she left her mark on me.