u/jessieknees

I was traveling for work, again. I got to the airport early so I could take some late breaking calls from the lounge. Sat at the bar, laptop open, doing calls. Oh yeah, did I mention that everyone was out when I was leaving, so I took the opportunity to get dressed, makeup, wig, dress, heels, stockings, the full deal?

Uber to the airport, slightly awkward TSA encounter that got resolved as soon as I used my masculine voice, and I’ve was off to the lounge.

Back to the bar… Finished my calls, conversation with cute guy, enjoying myself, next thing I know, his hand is on my thigh. Holy fuck, is this happening?!?

This lounge has gender neutral bathrooms, and before long I found myself in one of them, seated on the commode, with a mouth full of nice, hard cock. Fuck, he’s equipped. Fortunately, I had condoms and lube in my purse, so that mouthful quickly turned into an ass-full of hard meat with us both standing and my hands up against the back of the wall and my plug on the counter. OMG, this guy fucks.

It felt like hours. Days even. He took me as his, and I adored every second of it. Afterwards, I emptied the condom into my mouth, he kissed me gently and deeply, I fixed up my makeup, I put my plug back and we went our separate ways.

10/10, would repeat.

So there I was, on the road again. A string of meetings over the course of 2 weeks. Fly to Atlanta, there for a couple of days, hop in the car, off to Charlotte for a couple more days, on to something in SW Virginia, then a weekend in Pittsburgh with more stuff there on Monday, then Erie, Buffalo, and finally Detroit before heading home. Did you know it's shorter to drive from through Canada to go from Buffalo to Detroit? Like a LOT shorter. So, just about 2 full weeks on the road, and oodles of Jessica time. Heavenly!

Did I travel dressed? Certainly, though cute and casual, mainly. Before hitting the road from my thing in VA, I did my nails. Nothing crazy, some sparkly red press-ons I got at Ulta. I drove in some leggings and a tshirt with a bralette I got from Torrid underneath, with my C-cups installed, rounded out with my mid-back auburn wig that I kept pulled back with a scrunchy.

Arrived at the hotel in Pittsburgh (remember, I'm a Marriott girlie, so I stayed at the AC in the Strip District). Fun vibe, and great lobby bar. Was there awkwardness with the girl at the front desk confused about Jessica vs my government name? Naturally, but we were cool in the end, and she upgrade my room to one floor from the top with a river view. Showered, shaved (again), made sure I was just like I prefer, hairless below my eyebrows, and got ready for my evening. This time, it was a bit more naughty. Black crotchless tights, red bodycon dress, sparkly red 4-inch heels and the blonde wig. I was plugged, caged, and ready to meet somedaddy.

If you know the Strip, you may know about Club Pittsburgh. It's a bath house, gym, and all-around fun space a block off Smallman. I made a beeline, and started checking the place out. I'd only heard about it, and honestly, I wasn't ready. Before I knew it, I was center of attention with 2 much younger men, all so much hotter than I expected to be able to pull. Kissing one, the other behind me grinding on me, kissing my neck and giving me a serious groping. I was taken by the hand, and led to the 3rd floor, where we found the playroom.

I was relieved of my dress, leaving me in those crotchless tights and lingerie. The taller of the two, who I'd been making out with led me to a sling, where I became the focus of their passion. My plug was out, I was being fucked by one, while sucking the other's 7 inches, which he kept burying up to the hilt while his buddy's balls kept slapping up against my ass. As the boys traded positions, I noticed we were the central attraction on the floor, with 2 more guys joining us. A cock in my ass, one in my mouth, and one in each hand. I was being used as their fuck toy and couldn't have been happier about it. Condoms kept getting filled with their cum poured out into a cup, being saved up for me. Others came along and watched, jerked off into the cup as well, occasionally I switched off onto others, but mostly those 4 guys continuing to use my body and holes as their personal playthings. I experienced an absolutely mind-altering fully body sissygasm, leaving my whole body tingling and shaking. Did that stop the onslaught of their hard cocks? Absolutely not! More guys, more cocks, I lost count of how many cocks I had inside my ass, how many condoms were drained into that cup, but holy fuck, I've never seen that much cum in one place.

After what felt like weeks of being used, it was time for my desert. I rose to my feet, toasted these fine men who brought out the woman in me, and downed their seed in a single gulp.

Totally spent, I got dressed, and was walked back to my hotel by one of the boys, who I invited to stay. He was happy to do so, and naturally, I showed my appreciation in the morning by waking him with a blowjob. We fucked in the shower, and I spent the day strolling the Strip seeing shops, that weird museum of ketchup, and eventually met up with the two guys who I started with that evening for a more private setting up in my room. Good god, those boys fucked me as I'd never been fucked before, and I loved every moment of it.

Were there more fun and games on that trip? Sure, but this was the crowning glory of the trip.

[This was originally posted to the sissy confessions sub about a month ago, before I’d met the requirements to post here!]

I was out of town on a work trip last week. Orlando. Yeah, it’s Florida, but I was pretty tired of freezing. A week of thawing out was just the thing I needed.

I was feeling daring so I decided that I was going to travel dressed. My outfit wasn’t anything crazy - one of those adorable Halara EZ-Peesy dresses I got from TikTok and these super cute sneakers I found at DSW recently. Yeah, it was chilly, but I was heading to warmth so in just dressed for Florida and hit the airport. I wore a shoulder length brunette wig, did my makeup, and ordered up my Uber. Got through TSA with much less trouble than the news led me to believe, so off to the Admirals Club for a little breakfast and a comfy place to chill until boarding.

Bad news. Flight delayed, but on the plus side, I got upgraded (Executive Platinum has its perks!). Boarded, and found my seat. Here comes my seatmate, and oh crap. It’s a guy from work. Let’s call him Jeff. Fuck. I’m busted.

You can imagine how the conversation went. Questions galore. I’m a Marriott girl, so I was staying at the Swan Reserve. Turns out Jeff’s also a Marriott guy and also at the same hotel. Of course, I pleaded with Jeff to keep this between us. You can see where this is going by now.

For the next 3 days, I was male-presenting by day, and Jessica by night, as Jeff’s date, among other things. We even did the world stuff at Epcot as a “couple”. Suffice to say, Jeff is well equipped and did he ever know how to use it. I lost count of how many of his loads I took in my mouth, ass and even on my face. Not gonna lie, his cum is delicious. The man stays hydrated and drinks pineapple juice regularly.

Honestly? I need to plan another trip with Jeff! This guy fucks. Mmmm hmmm!

It was last summer. I was going through this non-stop horny phase where my appetite for cock was insatiable, but things just weren't happening. By way of Doublelist I met Jim, who lived a few towns over. I can’t host at my house, so my main interest is guys who can host, be that at their home or a hotel. Jim has an interesting setup for our rendezvous.

So, he’s a contractor, and his current client was away for 3 weeks, leaving him free run of their place. He wanted me to come over already dressed and made up with my wig on. Fortunately, I was parked in the garage and had the house completely to myself to allow myself to prepare and head out without anybody seeing me. I decided to go for playful. A quick shower and touch-up shave left me smooth from my eyebrows on down. I put my cage on, then some white crotchless/suspender tights, a matching white thong & bra, then this dress. I wore that with some cute white sparkle sneakers I found at the local DSW (what a score - they almost never have womens size 13 on-hand). A blonde wig and some makeup, and I was out the door. Not gonna lie, it's a total rush driving around as Jessica. As if all that wasn't enough, I popped in my remote control plug - one of those Lovense Hush 2 plugs. I'd just recently moved up to the 1.75 inch one. I granted control to Jim and hopped in the car.

While driving over, we chatted about our mutual desires ranging from kissing/makeout sesh to get things started, the ways he intended to feed me his cock, and fucking me in all manner of positions. Personally, my favorite position is on my back with my legs wrapped around my man or up on his shoulders while he pounds away at my sissy hole. He was all too happy to oblige that desire of mine. ;) Along the way, he kept changing up the plug's vibration patterns and speeds. OMG, I could barely take it.

When I was pulling up, I found the garage door opening to allow me to enter without the neighbors wondering who the strange woman in the Sissy dress is. The garage closed behind me, and there he was. 6'2", sandy brown hair, clean cut, and more attractive than I expected. Quite the gentleman, he opened my door for me, extending a hand to help a lady out of the car. I thanked him with a kiss, which started as a quick one, but spilled over into an exploration of tongues. Glad I wore that transfer-proof lip color!

I was led inside by the hand, taken to a large suite-like bedroom that had an already opened bottle of wine on the table next to a couch. We sipped some Rosé, kissed, fondled, really got things going. My clitty was leaking like a faucet, struggling against the cage. Such sweet denial... I had an impression of his size from the fondling going on, but I wasn't prepared for what was waiting for me in those jeans of his.

Moments later, I found myself on my knees in front of this man, practically drooling at the thought of what I was about to savor. He stood up, I unbuckled his belt, and found he was wearing button-fly jeans. Such a tease. Finally, success. I was about to see what I came here for. I wish I had a video of my face. I'm sure I looked like one of those girls in those porn videos where the girl's shocked at the size of her man's cock. That was me to a T. He was huge. Easily the largest I've seen. Every bit of 9 inches, and I could barely get my mouth around it! I was sure glad to have put my plug in earlier!

I'd love to claim credit for it, but he was fully erect after just a minute or 2 of my oral worship of his cock. It was time for Jim to lay claim to my backside. I got back on the couch, ass up in the air, back arched, ready for Jim to rearrange my insides with that beast of his. He removed my plug with a subtle "pop", and I knew it was time. I heard the condom going on, but got a very nice surprise first - and girls, let me tell you, this man can eat some serious ass. I've been rimmed before, but nothing like this. This was pure artistry. That tongue of his is fucking magical. I was warmed up, and half crazed from how horny I was at that point. Jim grabbed that little black bottle and proceeded to lube me up and squirt some more over the length of his shaft, taking a moment for a couple of strokes, and at last, the tip of his cock was tickling the outside of my hole.

Jim was so gentle at first. He pushed with slowly increasing pressure, taking his time. When he slipped in, I winced for a second with a slight bit of pain, which subsided quickly, giving way to his strokes in and out. We swapped positions after a bit, with me sliding up and down on his member, and finally, we switched again, leaving me on my back, just the way I love it. As a man, I've never been one to last terribly long, but Jim? Such control. He just kept the pleasure going, seemingly endlessly. I can't swear to it, but I really think he fucked me for a solid 30 minutes and still had not yet cum. I lost all track of time once I was on my back and his cock kept on sliding over my P-spot. Heaven on earth. After what felt like days of my pounding me, I felt something welling up deep inside me. OMG, it was going to happen. The pressure kept building and building, when suddenly...

I passed out of all time and space. Like that scene from Lord of the Rings. During this transcendent experience, I had the most intense orgasm of my entire life. My whole body shook as those waves of pleasure overcame me, cum streaming out of the cage and all. Meanwhile, Jim was still going, my legs wrapped around him, drawing him all the way deep inside. Finally, Jim's breathing started to change. He was about to release! He withdrew from inside me and pulled off the condom, offering me a taste. Who am I to turn that down?

Confession, I drained that condom, and let his seed coat the inside of my mouth. I don't know what this man eats, but his jizz was delicious. He big-spooned me for a while, until he was hard once again. How? It had only been about 5 minutes!

Well, suffice to say, I got fucked again, and had a second condom full of his sweet nectar to taste. We showered, cleaned up and I floated home. We had more encounters of course, in various locations too, but I'll save those stories for another evening. This is already long enough!