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Straight crossdresser first time meeting (part 3)
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I got off his lap and got lube to jerk him off more. Lubed him up nice and stroked his cock tight and slow and fast and put our dicks together and jerked us both I still really wasn’t hard. He loved our dicks together, I wish I was turned on to get hard. After stroking him for a while I got up and got a towel, wiped the lube off his dick. oh god what was I doing. I laid back down with my face down near his big hard cock. Just looking at it and really thinking about if I was really about to do this.

I went for it and put my mouth on his cock. I sucked the tip while stroking his shaft and I could tell he really loved it by the sounds he was making and the way he was moving his legs. I think I was doing a pretty good job for a first timer, I was just doing it the way I would like it to be done but also I have a terrible gag reflex so I definitely could not put it in my mouth very far, I just sucked the tip. I think I was sucking his better than my girlfriend sucks mine.made sure to suck nice ant tight and swirl my tongue on his tip and play with his balls. I mostly just kept stroking it nice and tight for him and sucking the tip occasionally and also having a break once in a while to kiss him, he had no problem kissing me after I was sucked him.

I’m sure I looked like a total slut with my dress pulled up and my panties showing and messy red lipstick. I know he loved it though since he kept feeling my body up and telling me how good it felt. He mentions he almost ready to cum so I gave his tip one last good suck then put a bit of lube on my hand and gave him a nice tight and fast jerk and got the towel ready to clean up his cum. He tells me he’s gonna cum and I said good boy cum for me, show me what I did to you and he shot his big cum load on his chest. He was so happy. I felt so good knowing I made this hot straight guy cum so hard. I helped him clean up a little then he just lays there naked and heavy breathing, so I kissed him again and laid beside him and cuddled a bit. He was reaching in my panties and rubbing my soft dick, I really wish I could have got hard for him. He really wanted it hard, but I guess I am just too straight.

Once he was good, he said that he better go since he had to work in the morning. He went in the bathroom to pee and cleanup and I told him to stay in there until I tell him to come out. I quickly changed into my sexy little maid outfit and told him when he could come out. I felt like such a slut but I wanted to show it to him. He came out and had a super happy look on his face and he rushed over to me and started feeling me up and he sat me down on the bed and we kissed again as he felt my body up and admired my outfit. Then he said he really should go and so we hugged and dapped up like guy friends and he left. He has only messaged me a couple of times since then and now has stopped responding so I’m not sure where that leaves this. Maybe he got guilty or ashamed of himself for doing that or maybe he didn’t actually have fun and he was just being nice. Maybe he got a girlfriend or found a different crossdresssr to play with. Makes me a little sad because I thought it was fun and was hoping to hangout with him again sometime since he was the only person I had done anything like that with.

Totally was not expecting things to go the way they did but definitely not complaining.

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1 year ago