All Comments on 'Rm 209: First Sex as a Crossdresser'

Would like to read more.

Great story, with an excellent balance between self-reflection and pure, raw, animal sex! Keep up the great work.

Enjoyed your story soo much! As a CD for the last 20 years I can still remember my first kiss, first BJ I gave and the wonderful feeling of being mounted by a much bigger stronger man. You immediately want more and I bet you have a lot of true stories. Kisses

Thanks. Enjoyed it very much. Decided to type this note before I jack off, lol.

When one accomplishes a goal and achieves their dream it is a wonderful feeling. This story captures the real emotions of the first time. Good writing.

Just an observation. Some CD's want to get fucked in the ass like a woman but not ever single CD wants that. Just sayin'.

I'm about where u were here, I need a huge cock , 10 in at least I've sucked a couple of cocks but my mistress fucks me with a 12 in and bigger dildo, I dream of a 14 15 in cock pounding my sissy slut ass would be a complete fantasy to suck another at the same time , anyone in central tx fit that bill , text me 5127344160

Good for you. I will never forget my first time. The thrill of rolling the condom onto him knowing that within a few minutes I was also going to "become" a girl. Quite a few years ago now but a defining point in my life.

Xxxxx

Cherie

I think the author was jacking off when they wrote this because it's the SOS factor. Same Old Shit.

Yes, the first time, you never forget. On my knees, strong hands holding my hips, his cock moving in me, wanting to fuck me, my cock hard, leaking as he does, pulling me back hard onto him as warmth fills my insides, my cock cumming as he does. Falling forward, he stays in me, wants to be in me, I want him in me, his strong body covering mine. Never forgotten.

With my first time I travelled dressed sissy to meet the guy. He was also a CD but when he put his cock into my bum that first time I was so happy and although I found it hard work I loved being a girl with a man in her.

Like it, although after my first time I had cum running from me for an hour.

Liked your story, we don't forget our first time. We met, he was older, he said he liked the pictures of my pantyhosed bottom, now the question did I want to come back to his apartment. Yes and that's where he kept feeling my nyloned bottom until he slid them down and for the first time I felt a man sliding his cock into me, fucking me and leaving me with his cum, when he had finshed but still with his cock in me I stroked my cock relieving my aching balls. still love being fucked but will not forget my first.

It was time for me to deside as a cross dresser to have sex for the first time.I met a man at a adult theater who wanted to have sex with a cross dresser.I told him it would be my first time having sex with a man.He told me he would go easy on me so we both could injoy the sex.I showered cleaned all hair off my body.I sat and did my eyes eye lashes face make up red lip stick and red nails.All black bra thong garter belt stockings red high heels and a short skirt and sheer top topped off with a long blonde wig.I met him he was a older man nice looking and i could he had a big hard cock thru his pants.We talked and went to a large booth with a padded bench a glory holes on both sides.He started to feel me up all the while telling me i was a sexy girl.He started to take off mt top skirt and thong all while feeling me up.He started to suck on my breast and licking me all over.He worked up and down my stocking covered leggs and licking my balls and cock.He then started to kiss me hard on my lips.He then turned me over and licked up and down my back and over my leggs .He then started on my ass licking all over it then he put his tongue deep in my ass licking and sucking hard.My cock was rock hard and leaking precum when a hard cock poked thru one of the holes.He reached up and pushed me head and told me to be a good girl open my mouth and suck that hard cock.I parted my red lips and in it went.First cock first time sucking one i soon really like the sweet taste of the hard cock.He stopped licking and sucking my ass and now he replaced his tongue with his now hard cock and started to fuck me deep and hard.The cock in my mouth exploaded and shot cum filling my mouth forceing me to swallow hard.All the while he was fucking me.I no sooner finnished one cock many more found their way in my open mouth filling me with more cum to swallow filling my belly.Now he was filling my ass with all his cum.

Loved your story. Wish that was me with you.

My first time, I wasn't 'dressed' that would come later. I literally seduced the guy, Soeone had said to "watch my back because he was 'shirt lifter" and we were flat mates in a remote area. after that warning, was lying on my bed and he on his, I just kept rolling my underpants down until I felt him sitting on my bed. He rubbed my bum cheeks - I liked it- ( I should say I was extremely nervous and very young (17) . I felt him pull my underpants all the way down and climbed on top of me, I could feel his hard on (first time ever for me-feeling another mans dick) he pushed the head against my ass hole but it was too tight and dry. He spit on his hands and put it over his dick and then was able to get it in. H tried to reach around and touch my dick but I wouldn't let him , he wanted to kiss and nope! so he fucked me, came in m y bum and then asked if I wanted to 'clean him up with my m mouth" nope! so that was it, no romance. no chocolates, bu believe it or not, I loved it, He was fairly small ( I think) it didn't hurt and it was pretty quick. He moved out of the unit next day .Next time was some years later. Then I wore , as I still do, pretty panties and a touch of lipstick.

Lucky girl iv never had the pleasure of a black cock yet. I started secretly dressing in one of my sisters things and wished i was a girl able to go to school in a little skirt and have boys chasing me. Ill never forget the first time i dressed as a girl for a friend and became his girl kissing touching sucking him then him taking my pantys off spreading my legs and rubbing his cock against my bumhole. I wanted him in me and pushed towards him and he pushed into me and we had sex. I never thought about condoms or did he we were just hot and horny and needed sex and we did with him grunting me panting and he spurted into my bum for what seemed ages. We continued doing it every time we could be alone and a few times came close to being caught by one of my sisters but always managed to get away with it. Now i have my own place and lots of things to wear and have sex with men a few of who are older mature married men who get from me what they dont get ànymore at home. Iv been complimented on how good i suck cock and how good it is fucking me. I do love a good spanking and really love men who like taking me outdoors dressed as a girl to have hot exciting sex the thrill and buzz is just amazing. Love to you all from Paula in the UK. Ps i show myself on cuckold chat most days in the sissy section if anyone wants to see my pics and cocks fucking me xxx

Sounds like you got what you needed. My 1st fuck was a large black cock in a cheap hotel. I had sucked a few and crossdressed a few times for Halloween. I always wondered what it would be like to be a cheap white slut used in a cheap hotel by a black man I had never saw before. I made plans, my wife went on a girls vacation. I went on a GURL weekend. I posted an ad saying I wanted to be used by a black man. I would get a hotel, dress up like a cheap slut and when he got there I would unlatch the door and go lay on the bed, he was to come in, lock the door and take what he wanted and leave. He took me in every way possible and left me lying on the bed with a sore rear and a face covered in cum. I have repeated this several times when my wife takes her girls vacation I take a GURL weekend. Last time I told the guy I wanted to roleplay rape.. He brought 2 friends with him but forgot condoms....... I tried to say no bareback but they laughed