I've had sex before, but only in boy mode. Yesterday, Saturday, I finally lost it in Sissy Mode.

Now Ive had Grindr for about 2 months now. With no luck finding a guy. First month was boy mode, second month was "aspiring sissy" mode. Had some suitors, but only one hook-up. So this past Tuesday I decide to do some profile editing. Sure as shit I got a message. He started off with a pic of his self and his BBC....I'm not one to judge. We chat for the better part of the day, also during this time O get more messages, but nothing serious. We talk about our schedules and figure Saturday will be the best day to meet.

So Friday night, I Nair all my remaining body hair....i usually keep it smooth, just getting the few that survived. Leaving a landing strip(cuz i want one) but it is faint. On Saturday, after work, I shave my face and prepare my pussy. I drive out to the hotel and book a room. Once in the room, I undress boy clothes and start sissy mode. Text him that I'm at the hotel then get into the bathroom and do my make-up. Eyes, face, lips, and nails. While nails are drying I get dressed. Breast forms, pink lingerie, stockings, thong panties, even this weird garter belt thing that the set came with. Put on my Wig and brush it out.

Take off the wig and hang it up. Then lay down and watch some TV awaiting his text. A few minutes later he texts me that he is on his way and that he will be about 1/2 hour....so exciting. At that point I lube up my plug, insert it, and go back to TV. About 40 minutes later he texts me saying he's here and is on his way up. I get off the bed and put on my wig. Seconds later, he knocks. I stare through the peephole and make sure its only 1 guy. I open the door and greet him. He tells me I look pretty. He gets in the room and gives me a little kiss(no tongue action, which I'm OK with). States he needs to use the bathroom and I wait patiently for him. It seems like an eternity, but only is like 1 minute. He exits the bathroom and starts to undress. He fondles my tits and my body.

Then he lays on the bed. I crawl over his body. Kissing his chest, then kissing my way to his tummy, kissing further to his cock...."shit I forgot my hair tie" runs through my mind. He's bigger soft then I am hard. solid 7 inches. I start licking his shaft, his balls, his sparse pubic hair, his head....all while shrouded in my hair...ughhh, I want him to have a better view of me. He gets fully erect, he's a shower, only adds about 2 inches, so up to 9, still pretty thick though. I suck his head into my mouth, twirling my tongue around it while it is inside. I start bobbing up and down on his cock, sucking it, enjoying it. I go for the deep throat. My face buried in his groin. My tongue dances around his shaft. I come up for some air. "Spit on it" he tells me, I oblige. He slaps me across the face with it...whatever gets him off. I catch it in my mouth and suck on it some more...."this fucking hair" still in my mind. Then it hits me.

I stop blowing him for a bit, grab my boy thong and tie my hair up and out of my face...so much better now. I go back to his cock. More deep throat action, more use of tongue(very important to use the tongue girls). "Ride me baby" is what I hear him say, "ohhh I'm finally gonna get fucked" is what I'm thinking. I release him from my mouth. I stand up, facing away from him. Drop my panties down and remove the plug. Grab some lube and smear it on my pussy. Then I open a Magnum, turn around, crawl to his standing cock, and put it on him. I suck him for a little bit with the condom on. Quickly grabbed the lube and poured some on the head.

I crawl back onto the bed and straddle him. I sit up and grab his cock from behind my back. I aim his tool at my pussy push the head in. It feels so good. After a few seconds I start to slide down, resting, adjusting to this intruder, now I'm all the way down. A few more seconds of adjusting and I slowly started to ride him. Up and down, up and down. Slow at first, but picking up some speed. Then he takes over, starting to thrust in me. I curl my feet under his legs and he starts to go to pound town. I start moaning....and my nose starts running. After some time, I have to excuse myself to blow my nose, but I hop right back on afterwards.

I'm rocking on his cock and he takes over again. Pure bliss, I start moaning again. After a few more minutes of scrambling my insides he states "I'm gonna cum"..."Don't cum yet" was my response....I wanted a facial, but it was to late. I sat on top of him, rocking, hoping for a round 2, but it wasn't in the cards. I reached to the nightstand and grabbed my phone, with him still inside of me. Got him to take some pics of his cock in my ass. Then some more of me going AtM.

He got up and showered. I laid on the bed in my afterglow of getting fucked. When he was done, he got dressed, exchanged pleasantries, and left. Stating we had to do this again, he wants me to be his personal sissy...I'm all for it.

​

TLDR: I got fucked for the first time in sissy mode.