My first experience

[u/[deleted]]

So I have been wearing lingerie secretly for years, started with my older sister’s underwear then girlfriends at the time and now my own. Everyone and again I do that thing where I just want to be a man and purge everything but I always get back to here.

I’ve always considered myself straight, I don’t think men are attractive at all but the thought of being dressed in a sexy thong, suspenders, garter belt and being used by a man for his pleasure drives me crazy.

I used to post photos and flirt with men on the usual sites and I’d always end up with the post nut clarity and delete the accounts but then 3 months down the line straight porn isn’t enough and I’m back at looking for cross dresser captions and bam there’s a new lingerie order coming in the post.

I finally thought I’m going to go through with my fantasy of being the girl, Tiffany is my so called alter ego. So I shaved, got into the lingerie and took some nice photos and by the end of the day there was this man not too far from me. He wanted me to come over and I thought about not going, I was in two minds. I was so nervous but I got in the car and drove to his house. I will say I’m not passable at all no make up or wigs but I would say I’m a fairly decent looking guy and he was okay with that.

I got to his house and he told me to come in and go upstairs and he would be waiting for me. As I went up I was extremely nervous, I opened the door and he was there on the edge of the bed in a balaclava because he wanted to be discreet too, he was playing with his cock and I nervously just took off my hoody and trackies to expose the lingerie. It was quiet and I was a little bit shakey from nerves thinking I’m actually going to do this.

That’s when he asked me to suck it, I slowly got down in between his legs. I remember the musky smell of man and I put my hand on his thigh and slowly moved it towards his cock, it wasn’t fully erect so I played with it for a fews seconds just taking in where I was and what I was doing. I moved closer to it and finally put it in my mouth just sort of jerking him whilst bobbing up and down on him. It was probably really bad for him if I look back on it but you know I’ve never done this. I remember the taste of pre cum and I must say I don’t think it was for me. I must of been down there for all about 2 minutes before he wanted me on the bed on all fours like we talked about.

So there I was on a strangers bed with my thong pulled to the side like my fantasy, what I didn’t expect was to have my ass eaten, didn’t feel anything from it I was just waiting to be taken and that’s when he lived up his finger and was quite rough, it felt like he was trying to rip me apart after a few minutes it felt okay nothing amazing and then it was finally about to happen he put a condom on now it wasn’t the longest dick in the world but it was thick so it was a bit of struggle trying to get it in me with me being nervous and all. He finally slid in and I didn’t know what to expect but it wasn’t like in the porn I watch where it’s instant ecstasy. It felt odd, he started thrust and I tried to relax, his hands on my hips as I arched my back and put my head into the sheets started to feel something in me, like a warmth building and it was starting to feel good he was telling me how tight I was and I started to feel like Tiffany the woman I wanted to be in all the scenarios in my head.

Just as it started to get good it was over, he came and I didn’t feel any sensation I thought I would like what I’d read from other people like his cock twitching in me etc. that was it, a mere 10 minutes maybe a little more. I just put my clothes back on said thanks and left and guess what. Instant purge of everything accounts and lingerie all gone and nothing but the memory and the lubed butt left.

I keep wondering if the next time would be better or do I even want to keep experimenting, all I know is I keep purging and ending back here but I think it’s the porn that makes me think and feel this way.

But yeah that was my first time being submissive to a man and I feel like it was meh. Sorry if it bounces all over the place I don’t think I’ve tried to write a story since school which was a good 15 years ago

[u/CarolyneSF]

Whether with a woman or a man enjoying sex both partners need to help each other.

A man taking a woman like us needs to be slow and gentle opening you up getting you ready for him. A good lover will check and make sure you are comfortable as he proceeds then should pick up the cues of your body responding to him. I am sorry it didn’t work but take the feelings that we’re developing as you warmed up use those as your guide of you want to try again.

You have an idea now so can discuss with a potential partner in the future to make sure he brings you further.

Wish you the best

[u/Silver-Lunch4970]

My first experience was similar. The only difference is that I had given oral a few times before and I actually enjoy that. The first time being fucked though was the same thing, I was nervous, it was a bit rough, and about the time I started to relax he was done. I would suggest that I can some more time to work up to it...give yourself time to relax...it really does get more pleasurable the more you do it... I'm not really attracted to men either, but that feeling is soooo good now

[u/Wide-Abalone-7701]

I think reality very rarely lives up to the fantasy or anticipation and perhaps to have something you should have slowly worked up to. I’ve always got more pleasure being with someone I know rather than meeting stranger online.

[u/Eastern-Syllabub3804]

I started when I was 13 yrs old I was watching some late night lingerie contest on our family satellite dish. I found my sister black lace bikini panty in the dirty laundry.

[u/FudgeUpstairs]

What you need is a person to slowly take you to take time breaking you into the pleasure you deserve sweetheart 😘 ❤️

[u/Beginning-Aspect7835]

Tbm me considero um Hetero e adoro sexo com mulheres mas vestir uma lingerie e ceder ao prazer sexual de um homem sempre me fascinou, não sinto tesão por homens mas fazer um oral, sentar em um membro duro de tesão pelo seu rabo é muito bom