“Wilson, over here,” one of the guys yelled from a corner booth in the hotel bar.
“Hey, Smitty,” I said as I approached the table. Another four or five guys attending the same conference were well-ensconced in the booth, and I was already several drinks behind them.
“Pull up a chair, let’s get you a drink,” he said. “I still owe you one from that last merger you helped me with.”
“No can do. I’m meeting an old pal from Army days,” I said. The lie came easily because saying “I’m meeting my online crossdressing trans-lesbian girlfriend,” while true, wouldn’t be acceptable in my social circles.
“Aww, c’mon, Wilson. What are you, some kind of sissy?”
My clitty twitched involuntarily inside the pink satin panties I was wearing under my drab clothes. “Yes, now line up and let me suck your cocks,” played in my head while I vocalized my answer.
“What are we, in high school? Grow up. You can catch me tomorrow. And no cheap shit, either. You owe me a real drink!”
With that, I made my way to a pub-height table in the opposite corner. I sat down and waited patiently, watching the door. The waitress came over and I waved her off, telling her I was waiting for someone to join me.
Jaymie and I had been online girlfriends for years — first Tumblr, then BDSMLR, and finally Twitter. We had exchanged emails and shared so much of ourselves anonymously that I worried meeting might ruin the friendship we had developed. I think deep down, she felt the same way.
Although I travelled a lot for business, this was the first time we had been anywhere near each other, and the temptation was too great. She rejected my suggestion at first, but my begging and pleading had worn her down. We had tentatively agreed to meet, though we both had plenty of reservations.
She would be arriving in her drab clothes, too. I scrutinized every single guy who walked into the bar, watching for any telltale signs of the one I was to meet. I had seen her face en femme just a few times, but wasn’t exactly sure who I was looking for. She had no idea what I looked like.
As our time to meet ticked by, I began to wonder if she was bailing on me or not. I checked my Twitter messages. Nothing.
Then I saw her. There was no doubt in my mind that it was her. Her eyes darted around the room nervously, and her face was pallid. As she scanned the bar a second time, I raised my hand in a tentative wave. She was dressed in her drab “boy clothes” and had a small duffel bag slung behind her like she had just come from the gym. As she approached, I stood. We extended hands, and as we shook, I pulled her in for a “bro” hug.
“Jaymie, love. I told my colleagues you’re an old friend from Army days,” I said quietly in her ear. She hugged me tighter and held the hug just a few heartbeats more than I would have.
“Oh, Stacey, I can’t believe we’re meeting at long last,” she said in a breathy whisper.
We parted and sat on opposite sides of the table. I motioned to the waitress. I ordered an Old Fashioned, and she ordered a margarita on the rocks. I had decided to avoid beer because I didn’t want to feel too bloated later. I didn’t know what the night would bring, but I wanted to feel up for wherever it took us.
We made small talk as we sipped our drinks. It was all I could do not to reach across the table to hold her hand. I could tell from her body language that she was fighting the same urge. My friends in the corner had gotten loud and were bordering on the obnoxious.
“Shall we finish...” I began to say.
“Maybe we should go...” Jaymie said at the same time. We both laughed.
I flagged the waitress down and signed the check to my room. As we stood, I felt butterflies doing loop-the-loops in my stomach. Jaymie bent over to pick up her bag, and I couldn’t help but feel reassured by what I saw — a clear panty line under her pants. I suddenly felt calmer.
I gestured to guide her toward the elevators, watching that panty line wiggle invitingly in front of me as we made our way out of the bar. I was hit with a sudden thought — could the guys I knew in the corner see my panty line as I walked away? I shrugged off the thought and followed Jaymie.
I swiped my room key, and the elevator began to rise. We tried to make small talk, but it was just too hard to maintain. We were both thinking about what was about to happen when we got to the 17th floor.
“I just want to press you against the wall and grope you while we kiss,” I said suddenly.
“Ohh Stacey,” she said. “I want that so much!” We both laughed nervously.
“It would sure make the guy’s day who reviews the security footage, I bet,” she said.
Jaymie shifted the bag on her shoulder, swinging it around so that it bumped into me. Her hand followed, and I felt her groping my swelling clitty while her hand was hidden from sight. I tried not to react like someone was rubbing my crotch.
“Ohhh, you’re being awfully naughty!” I said.
“I’ve warned you for years that I wanted to get my hands on this,” she said, grinning from ear to ear. The elevator dinged as we reached my floor. She gave me one more firm squeeze and then left the elevator. I told her my room number and we wound our way through the halls.
“Nice panty line,” I said. “I can’t wait to see what panties you chose.” She passed my door and let the bag fall from her shoulder, bending over to pick it up. She wiggled her butt slightly as she did so.

I opened the door and stepped inside. As Jaymie closed the door behind her, I tugged on the strap of her bag, pulling her off balance and into my waiting arms. My hands slid down to cup her ass as her mouth found mine.
I briefly considered that we must look like two men kissing, but the thrill of kissing my longtime girlfriend banished such doubtful notions. Our tongues chased each other as I steered her to the end of the bed. I broke our embrace and gently nudged her to sit on the end of the bed.
I sat beside her, pushing her back and moving to a prone position beside her. I rolled onto my left side next to her. Her mouth sought mine again, and while we resumed kissing, my right hand clawed at her waistline. I tugged her belt open and fumbled to unbutton her pants.
“Oh, Stacey,” she said. I felt her hands on my belt, too.
We were both breathing heavily between open-mouth kisses. I succeeded in opening the front of her pants. A flash of dark satin, and I knew she was wearing my favorite pair of her black satin panties. Her clitty was already hard.
She moaned aloud as I squeezed her shaft, slowly stroking her inside of her panties. Her pre-cum flowed from the tip, soaking the satin as I continued my ministrations.
“Ahhh. Mmm. You’re such a naughty tease,” she said. She opened the front of my pants, and her left hand slid inside. “Ooh, you know I have a weakness for you in pink.”
“Oh, I’m not teasing you, Jaymie,” I said. I started stroking her faster. Gripped by my fist, she squirmed inside the slippery satin of her panties.
“Say it again,” she said. “Say my name, Stacey.”
“Jaymie,” I said. “My dearest Jaymie.”
“Ohh, Stacey.”
“Cum for me, darling Jaymie. Cum for your sissy Stacey in your black satin panties!” I squeezed her shaft hard and then shortened my stroke, concentrating on the tip.
“Oh God, Stacey! Not yet! No! Oh, I’m cumming! Unnngghh.”
I felt her hardness pulsing and throbbing in my hand as she pumped her first load into her panties. Already soaked with her pre-cum her first hard spurts forced the white cum through the wet satin, oozing in stark contrast against the black. Her hips bucked gently as she surrendered to her passion, writhing against my hand.
As she came down from her orgasm I peeled back the waistband of her panties and slid my tongue into the puddle of cum. I closed my mouth against her flesh and slurped greedily. As I pulled back, a single sticky white string of cum connected my lips to her clitty. I followed the string to its source.
I was paralyzed by that first electric touch of my virgin tongue to the tip of her clitty. She gently pulled my head forward, sliding more of her clitty into my virgin mouth. I closed my lips around the mushroom-shaped head and I sucked my first girl-cock.
The passion of the moment, along with my warm, wet mouth made her clitty begin to stiffen. She knew she was already leaking more pre-cum, and knowing that I was tasting it brought a smile to her lips.
“Ohh, yes,” she said as her girl-cock twitched and swelled. Her voice was almost breathless. “Suck me, Stacey. Your mouth feels so amazing.”
“Mmm,” was the extent of my reply. I didn’t want to release her from my mouth to speak words.
“Deeper, babe,” she said. “Take as much of it in as you can.”
One of her hands moved to rest on my head. Her other hand left the aching bulge in the front of my panties to join its mate. Her hips slowly rose as gentle pressure was applied.
“That’s it, honey, every last inch.”
I pushed forward, encouraged by the pressure of her hands on my head. As her girl-cock hit the back of my throat, I opened wider. With a loud gluck, her entire length disappeared down my throat. My mind registered that she had now taken every aspect of my oral virginity — tongue, lips, mouth, and throat. Her cum-soaked pubes tickled my nose as she ground her mons against my face. I inhaled the musky fragrance of our depravity.
“Oh, Stacey,” she sighed as her hips moved her shaft in and out of my mouth, “You’re such a good sissy cocksucker.”
Jaymie moved to stand up and I moved with her to accommodate her without her cock leaving my mouth. As her pants fell to the floor, I was now on my knees with her hands gripping the sides of my head. Her girl-cock was so hard now that I was having trouble getting it down my throat, especially from this new angle.
Reluctantly I released her cock for the first time, sitting back on my heels.
“I want you to fuck my face,” I said. “Force your girl-cock down my throat and treat me like the sissy bitch I am!”
Jaymie stepped out of her pants and forward, pushing her cock back into my mouth. With a firm grip on my head she pulled my mouth on her cock and pressed past my gag reflex.
“Good girl, Stacey,” she said. I felt her pubic hair against my nose again as her balls mashed against my chin. She clutched my head against her groin.
“You’re such a good sissy slut.” She began moving her hips, sawing her girl-cock in and out of my throat.
“Take it! Take my dick. Take my dick down your cocksucking throat!” I looked up at her and saw that her face was a mask of pure lust and pleasure. I smiled inwardly. It was almost all I had ever wanted.
