Yesterday evening I had my first sissy date. I was super nervous and anxious that I would dissapoint him. He was so lovely though! We had met earlier for a "get-to-know" date without any sex and he was just as sweet as then. I also shared my location with my friend because I'm rather safe than sorry.

For preparation, I shaved my body, put on some lotion, painted my nails pink, put on my pink panties (my first and only as of now!) over my plug and a cage. I have no issues going out with makeup, so I had a very subtle one (because I'm still new to make-up). I also bought a dark purple lipstick but kept that off until I arrived. I put my skirt, condoms and some wipes into my bag and left hor his place.

I arrived at his place around 6:30pm and he immediately complimented my look and I felt very pretty after I changed into my skirt :3 We talked again about do's and dont's and had a consent talk. My nervosity didn't go away completely but after about half an hour of talking I felt ready for some naughty fun. We started kissing, and I actually initiated! (I'm so proud about that!). We made out for some time and he slowly moved up my thigh, under my skirt.

He pulled me onto him and had me straddle him that way. We made out some more and I rubbed myself on him. When he pulled my panties to the side and found my plug, he had me moaning because he slightly pushed it in further. By that time, I already leaked a bit.

That motivated and excited me so much, that I whispered into his ear, trying to be seductive something like "I wanna taste the rest of you now". I also had to giggle because his mouth and the whole area aroudn it was full of smeared lipstick :D

Anyway, I slid down the couch and between his legs and thought about your tips you gave me yesterday :)

I teased him by slowly opening his zipper and rubbing the bulge with my hands before I pulled his cock out. He was already near rock-hard and I had seen his cock before on pictures but the real thing just looked so much better. It also smelled amazing! (in a good way :D) I started off by slowly stroking his cock, keeping eye contact with him, licking my lips. I couldn't keep myself from tasting any longer though, so I scooted about closer and slowly licked his shaft, from the base to the tip, from underneath. I then put my lips around his tip and used my tongue to tease it.

I moaned and kept eye contact with him while I did that for a while. I spit on his shaft and rubbed it across with my hands before I started sucking it. First, I had trouble with my teeth but I quickly managed to fix that. It took me nearly 20 minutes but by then I had like three quarters in my mouth. The last fourth was the most difficult because that didn't have place in my mouth. By that time, I had already gotten multiple compliments from him. I moaned and playedwith his balls when I started bobbing my head. My lipstick was smeared all over his dick and I was happy about that because that was my goal hihi.

I made sure to make some real nasty sounds. After a heavy breather, I asked him if he liked it, and he told me, he loved it! That gave me another push and I tried to take him to the base. I gagged a lot and long but at the end I managed. I kept him in as long as possible and felt like a real slut releasing him. Strands of spit were connecting my mouth with his cock. he asked if he could direct my head a bit and I gleefully nodded.

He was so careful and had me take only half his length and I felt quite comfortable. I put his hand in my hair (My hair is naturally long) and told him, he could go a bit faster and rougher, and he should just stop when I tap out. I'm telling you, thjat was the best tiem of my life! He started slow again but soon he had me take his whole length! I did have to tap out because I nearly gagged too much.

We agreed he wouldn't cum in my mouth the first time, so he warned me when he got close. We returned to slow sucking and I swirled my tongue in the area between head and shaft when he pulled my head back on my face, bent his dick towards my face and yelled that he was cumming. I closed my eyes and felt hot spurts cover my face. Near insticntively, I licked around my lips and got a taste of him. What can I say, I loved his taste!

the cherry on top was, thate he didn't mind his own cum because he pulled me up and we made out hard for a minute or two. He groped my ass and slepped it and I was leaking soo much!

We both calmed down and I went to clean myself up. I couldn't resist taking a pic of my used face. My make-up was ruined, cum and spit were all over my face. Afterwards, I cuddled into his arms while we had our after-care talk. He had prepared a glass of water for me and a little snack, he was soo awesome!

We both agreed that it was a very intense but good experience. We also deicided to watch some Netflix. I felt so safe with him! He had me in his arms, caressing my arms and thighs with his soft fingers. We also agreed to repeat that soon. High from this whole situation, I also asked him if he was solely interested in blowjobs or if he would be open to take my sissy virginity. He told me, and that's another thinbg I love about him, that he's definitely open about it but that we should get to know each other better first. That is what I so love! I'm not ready for that yet and I'm happy that he acknowledges it.

I felt so comfortable but still hungry for more, so I aksed him if I could slowly suck him off while watching Netflix. He gave me a kiss and told me yes. It took some time and at first I just stroked his cock, massaged his balls before he was ready again. I made him cum a second time over the course of about 45 minutes.

When I left, I didn't even bother to switch my skirt for pants again. We made out for about five mintues at his door and we agreed again that we would repeat and maybe continue this soon.

My thoughts: The whole process of getting ready for this date, the date itself and afterwards had me so excited. Of course, I was nervous and I will be the next time, and the time after that maybe too but that's okay. It's the good kind of nervous.

I felt safe with him, he is cute and wholesome, excpet when he's not. (He called me his throat slut when he controlled my mouth). He also offered to buy me an outfit or two, the only condition being that I snet him pics in them :3

Overall, this was an amatzing experience and I will soon repeat it!