[MF] I (MtF trans) hooked up with a waiter from my office canteen

English isn’t my first language but I’ll try my best. I’ve been working in my office for around 2 years and most of the days I eat my lunch in a big canteen. You order food and you bring it to your table but in some cases, a waiter/waitress will bring it if it needs more preparations. One of the waiters worked here before I did and was always very nice and funny. If we worked late and eating place was empty, he would sometimes sit with us and just talk and joke around as my coworkers knew him for years. I’ll just add here that at this point I wasn’t sure if he knows I’m trans or not. He behaved 100% naturally towards me.

Anyways, around 2 months ago I was back in office from remote work and canteen was also reopened and I was happy to see that the guy (let’s call him Michael) was back too. At this point there were many instances where I was eating alone (covid chaos) and the place was nearly empty. Michael came to talk many times but it was different cause we didn’t know eachother too personally and before I always had my coworkers with me. We spoke more and I started to like him, especially that he is attractive for me. I also noticed that he smiled a lot towards me and was more serious. I learned that he is single and I told him I was too. Somewhere around this time he asked for my WhatsApp and we’ve started to text on and off, with light flirting here and there. Now skip forward around a month, at second half of June I started to work from home again. Surprisingly one of my first thoughts was that I’ll miss Michael because he made me feel like a woman and I was comfortable near him. I was also horny so I decided to up my flirt game one evening.

We were texting a bit, he was a bit tipsy and I thought it will be good idea to activate his imagination so first step was to send him a picture. I took a pic of my wine glass but made sure that reflection of my cleavage was visible in cupboard mirror (at work I dress way less revealing). He liked it and responded with something like “wow” but I didn’t ask him more on purpose. Next step was to text him something that will make him imagine me or us in some hotter circumstances. So I asked him what we would drink and do if he would be here with me. He answered something that is hard to translate to English but roughly it meant that night is young/hard to tell. But I could tell that he didn’t want to answer with something innocent to not kill the chance with me but he also wasn’t sure if he can suddenly be very flirtatious so he was testing the waters. Unfortunately I didn’t feel too well so this time I had to go to sleep.

Next day was even more interesting. He texted me again which isn’t typical cause we didn’t text every day at that point. I was pleasantly surprised and flattered. We kept texting most of the day, I had to run some errands but afternoon I was free. Michael said he misses seeing me at office canteen so I came up with idea that maybe we could drink through video call on Skype to which he agreed. I was really excited, not gonna lie, we started at evening and it was really good to see him again, we drank some drinks and flirted, we were both really tipsy. At some point he says “I really loved that shirt you had on yesterday”. I immediately knew he meant the one that reflected in mirror on my pic but I pretended that I don’t know and said “What shirt? Ohh wait it reflected on cupboard? You were supposed to look at glass, not me” in flirty way. He said ‘Im really sorry but I can’t control my nature/instincts” which triggered something in me. Just a thought that a straight man looked at me in sexual way and wanted me, made me suddenly very happy and aroused. So I kept going and asked him if he would be able to control it if I invited him over. Not even 30 mins passed and he was on the way to me. I’ve sent him my address etc., quickly took shower, put on make up and that shirt with big cleavage. I remember that at this point my hands were shaking out of excitement and horniness. I’ve had my share of experiences with guys but I think never I wanted someone like I wanted him on that evening. The combination of him being so nice and kind towards me, him wanting me so much but yet being courteous. Me feeling sexy and feminine.

He finally arrived. He barely said I look beautiful and we immidiately jumped on eachother and started making out at my doors. I grabbed his head and pushed it in my face while he got a nice feel of my butt cheeks. After few seconds we stopped so he can take off his shoes and I immediately grabbed his hand and guided him to my living room where I have a big couch. I pushed him onto it so he sat and I got on his lap, guided his hands on my breasts and continued making out. I know you guys like to know how people in these stories look like so I’ll briefly describe before we move on. I am half asian half white, short (around 165 cm) and I was blessed (with power of E) with really big and natural looking breasts. I have long black hair and easily pass as a girl. I’m 23. Michael is a tall, pale guy, skinny, with curly, medium length hair. He is 30+.

So while we made out the only thought I had in my head was that I wanna let him do anything he wants with me. I craved for him and felt so good cause he fondled my breasts and it’s very sensitive. I took off my shirt and before I realized he was already sucking on them. Now I mentioned this in my other posts but during my transition, my nipples got very sensitive and I can get off by having someone stimulate them. Michael was doing it so well that I was going crazy. He kept them held in his hands while he licked and sucked my nipples, kissed them one by one and sometimes dove his face between them. I was moaning so much that I was embarassed. He then put a big part of my boob in his mouth and started to do motion like he is trying to eat it while also doing circles with his tongue and I was in such ecstasy that my head went back and my neck was so tense I couldn’t get my head up. I was basically sitting on his lap arched back, with his face in my breasts. I would fall on the floor if he didn’t put his hands on my back. I absolutely couldn’t move or fight it, his mouth had full control over my body. He knew how much pleasure it is so he kept going and didn’t stop even when I tried to say “stop, stop” without a breathe. Of course that drove him nuts and I could feel how hard he is with my butt. He gave me a light bite on nipple and to my surprise and embarrassment, I climaxed. I’m not sure if he realized that but he finally stopped, I was barely conscious but I went back to making out with him.

Usually when I’m in situation like this, I tell a person that I was born a man. Especially in last years because it’s harder to notice. But with Michael I just had this thought running through my head, I wanted his dick in my mouth, I wanted him to cum on my face or boobs. I was also sure he would be cool with it or that he even knows. Anyways I just craved for him so I took off his shirt, started to kiss his neck and ear, then I went lower and kissed his chest and nipples, then his belly. I licked his lower abdomen and tried to squeeze my tongue between his pants and skin. I was finally on my knees between his legs, my hands and legs shaking out of horniness, I remember my mouth being very watery because I was imagining what I will be doing with it in few seconds. I gave his cock a kiss through pants and went ahead to undo his belt and zipper, pull down trousers, pants and socks. He was hard and his balls were hanging low. I started to kiss him everywhere around and gave some circular licks on inner parts of thighs and eventually ballsack. I grabbed him and lightly stroked while trying to suck in his sack in my mouth. I was doing it pretty intensely because I couldn’t stop myself and I’m sure he noticed how much I craved for him because he was moaning in pleasure. I couldn’t wait anymore and gave him a long lick from balls to tip and at last slowly forced his dick between my lips.

Thoughts were running through my mind at this point, it was hard to believe that I’m kneeling half naked in front of Michael with his junk in my mouth, after knowing him for all this time, all those our conversations in canteen. I also felt immense pleasure from combo of feeling him being very hard, I could feel veins on his dick with my tongue, feeling the taste of his precum and feeling of pulsating. I sucked and pumped my head up and down, licked and gagged on him, I behaved like I was in the desert and tried to forcefully drain water out of him. Michael was moaning and pushing my head with his hand, twitching when his tip touched my throat. I grabbed him with my hand, stroked him and repeatedly moved my head up and down like I’m trying to pump everything out of his balls. He was in bliss. I didn’t want our fun to end too soon so I went back to slurping his balls while looking at him for few secs. I raised my body on my knees, and grabbed his dick with my breasts. He just whispered “oh my god” and was looking at me while I smiled and slowly started to move my breasts in repeating motion. Him watching my boobs getting fucked made me really horny. After a while I knew it’s time to let Michael bang me so I sat next to him and we lightly made out and a bit nervous, I told him I need to tell him something before we go further. He said “go on but if it’s something related to your genitals, it doesn’t matter to me, I’m going to do you no matter what”. I was absolutely surprised cause I had no idea that he knew but also him wanting to fuck me no matter what drove me crazy. I didn’t want to continue this and move on to action so I said “fuck me, Michael”.

He took off my panties, set me up on my fours on couch, used lube that I had on coffee table and started doing me from behind. He was gasping a lot and doing it pretty harsh so i knew he couldn’t wait too. I was in total ecstasy, had my eyes closed and moaned like a high schooler. He grabbed my boobs with one hand and raised me and grabbed my penis with the other and stroked it, all while banging me from behind. I was semi hard but it felt so good. He was slamming his abdomen into my butt cheeks and I just took it all and enjoyed him getting so much pleasure. I felt like real slut and it was amazing. He said he is close so we switched position back to where he was sitting, he spread his legs and I sat on his cock with my ass towards him and did fast squats to the point I could hear sound of my butt cheeks clapping on his lap. He was already cumming and I could feel he tried to push me off him but I stayed and took all of his cum inside my ass while lowering my tempo. We were both absolutely exhausted but satisfied. Was honestly one of hottest experiences in my life. We cleaned up and showered, he stayed over night and went home at morning. We talked during breakfast and curiosity was killing me so I told him that it’s not common that someone recognizes I’m a trans. To which he said that he didn’t know about it until he was told by my coworker. I was surprised because that’s pretty rude thing to do but he explained that he asked my coworker about me when I was absent because he liked me and she just suggested it, didn’t tell him directly. He combined those facts and realized the truth by himself.

Me and Michael did more crazy things later, if you want I can post other stories too.

Source: reddit.com/r/gonewildstories/comments/ohrj42/mf_i_mtf_trans_hooked_up_with_a_waiter_from_my