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The first time I bottomed for a girl

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  • The first time I bottomed for a girl

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    This is as taboo as it’s gets and I want to hear all about it. Since I’m making such a dark request allow me to be the first.

    My my only trip to LOS thus far was back in 2014. This trip starts after a nasty breakup with my fiancé. Whores and alcohol was on the menu. Being as I’m veteran of the United States Army infantry I knew a thing or two about what was in store, or so I thought...

    The event took place with a gem from the kitten club attached to the penthouse suites in Pattaya back in 2014. After a few days on the scene pretending not to be interested I caved and went balls deep. I had the club all to myself. We’ll say there were about 15-20 mostly sexy af girls. I personally do not like choosing right away (bad news for the ones that up at the door). My heart was racing and Mommason could tell so she shooed that ladies away and sat down with me and small talked about shit not related to the club.

    We got to talking for a while, drinks were pouring, stories were being told, all the while 15 or so divine beings twirled around on stage, exploding with eagerness. For a good while I thought mommasaun was going to have me for herself and I was cool with it. But.... my ego got the best of me and I wanted a 5 star bitch to take my ‘v’ card.

    Like magic, she appeared. I cannot remember her name but I’ll never forget how she looked. She was more feminine, pretty, soft, etc... than any GG I had ever been with. Funny how ladyboys put normal girls to shame... Are normal girls even relevant these days?

    I thought I was being baited but once my hand went down ‘her’ panties I knew I was in heaven. We agreed for her to meet me in 15 as I was still concerned with face and did not want to cause any uneasiness at the Shamrock. However, I foolishly walked out the front door and not through the penthouse suites. Cover blown? No. The girls at the Shamrock never did anything but smile.
    
    Once back in my hotel my heart began to beat with the intensity of the drums from jumanji. The phone rings...”sir, you have guest. Do you know she’s ladyboy?” Good looking out by the staff. “Yes, I do.” I replied. Know I’m feeling like I’m about to have a heart attack.

    Knock, knock... Fuck, she’s here. No turning back now. Good thing too because she was hot as fuck. There, at my door.... was a thin (maybe 120lbs tops), tan, feminine, gal wearing civies. I smile, heart still pounding, and let her in.

    She sets down her bag while at the same time I grab her from behind and start to kiss her neck. My hands move to her breast(bolts ons... I know sorry) and begin caressing her. My cock was already hard and felt like it was about to tear through my jeans. She took notice, spun around, and unzipped me.

    There was a lot about her indicative of female. Her hands were not gloves. Her facial bone structure was soft without too many guy features. Her muscle tone and overall body was that of a woman who actively runs. Her feet were tended to. Once my cock was out she blew me better than any gg had ever.

    Why is that? I’ve had my dick sucked plenty of times but ‘girls’ always do it the best.

    “Wow, this is really happening...”. I pulled her up to meet me face to face where we locked lips. Passionately, I kissed her completely forgetting the world outside. I un-snapped her bra and pulled her half naked body against me. Her soft skin felt incredible against me. I embraced her once more while undoing the button for her jeans.

    I made my way down south, kissing her in all the right places. She was wearing those compression undies that keep her goods close to the body. I pulled those down and was greeted by a ‘feminine’ tool. I had only one chance to walk away... She notice me hesitant and gently pulled my face In close. “Wow... she even smells good...”. So, I put her cock in my mouth and as if I had been doing this all my life gave her a memorable blowjob. I could taste her precumming and I really got turned on.

    Nothing sexier than looking up into the eyes of an angel and watching her moan with fulfillment, consumed as it were, with the energy created by us two souls.

    Passion was flowing (with a prostitute, I know) and we both wanted to ravage each others bodies. I positioned myself accordingly and felt the cold lube drip down my ass crack and onto my starfish. This was it.. this is going to happen. I felt a sharp jab and leapt forward almost putting my head through the wall. We laughed then she told me to relax. She massaged my back for a while while teasing ass and when the moment was right she entered me.

    Sexuality.... certainly questionable at this point...

    She was nice and slow with me. Pump after pump. It was an ecstasy I’d never known before. She wore a condom but I could still feel her release. Though , I clearly had just had sex with a prostitute, there was chemistry between us and we just laid there in each others arms and everyone outside of us two could fuck right off.

    Not a bad first time I’d say. Can any of you relate? I don’t suspect everyone had a great first time.

    -Fallen
    
    P.S. Come over to the darker side of the dark side... it’s more fun!

  • #2
    My first time was with a woman that I arranged to meet in Hong Kong. She was a Filipina from a bad part of Mindanao so I thought a week together in a city I always wanted to see would be best. This is the story of my first time.

    We got undressed and she took off her bra revealing her sizable tits. I kissed her and we necked while I fondled her breasts. It was obvious that both of us wanted to get to the main event. She pulled off her panties and there it was - her hard cock. It was about four inches but very hard and throbbing. I wondered if I would freak out seeing a cock for the first time and if I would think she was a guy because of the cock.

    In fact I saw her so much as a female that even with her cock in my hand, I could not see it as masculine but only as part of her body, the body of a woman. Was I in denial? Or being a realist? Who knows but I did not freak out at all.

    I took it in my hand and fondled it a little rubbing it up and down. Then I put it in my mouth and started to suck her and lick her knob. She moaned while I sucked her and I tried various ways of licking and sucking her hard tool. By now I was anxious to get it inside my ass. I needed her inside me now. It was like a compulsion that took over me to get her stiff prick in my ass.

    I got the lubricant and put some up my asshole and then put some on her cock and got it lubed up. Then I got on my hands and knees and presented my ass to her. This was it!

    I thought that she would take her time working her cock in my hole but instead she rammed the length of it up my ass in one thrust. It's a good thing she isn't seven or eight inches I thought to myself. There was a moment of pain but once she got it all inside I felt fine and I liked feeling her hard knob sliding in and out of my slippery wet hole.

    I was her bottom bitch as she got down to business fucking my ass rapidly and panting with excitement. Her hands grabbed my hips as she pushed in as deep as she could go. I knew that she was about to unload in my ass and I could feel her stop and start moaning while she had her orgasm. I couldn't feel her shooting her cum but I knew that she was filling my ass up with her jism.

    Here I was within five minutes, I not only had my first cock in my ass but I had her first hot load of cum injected into my bowels.

    After she had cum, she stayed in my ass and leaned up over me to tell me to wait and that she would get hard again. So we stayed locked in position like two dogs tied up together with her cock in my ass. It only seemed like a minute or two before her cock was getting hard and she started to thrust back and forth a little.

    Then she was completely hard and ready for round two. She was now fucking in earnest pushing her cock balls deep into my ass and pulling back but staying in my ass. I experimented squeezing my sphincter muscles around her cock and trying to pull her cock up inside my ass. For the most part though I let her do the fucking and just concentrated on feeling her movements back and forth in my anal cavity. It was lovely feeling her hardness in my ass as she got excited again and her movements increased in intensity.

    She had just finished pumping a load of her hot milk into my bowels but now she was getting ready to ejaculate again. God how I wanted her to cum and add to the pool of spunk up my ass. I felt like such a slut getting fucked twice in rapid succession but I didn't care. I wanted her to breed me again!

    She wanted it too and I knew that she was close to orgasm from her moans and cries. Yes, baby, give it to me I told her as she pounded my ass with her hard cock. Fuck my ass, darling, I begged her. Again she stopped her thrusting as she bottomed out in me and spurted her seed into my shit hole. She was having a good one I could tell and she cried in ecstasy as her cock throbbed and spurted her hot semen into my hole.

    Oh God, I felt so good. Again I couldn't feel her cock ejaculating but I knew what was happening back there. I was being bred like a bitch and she was completing our mating for the second time. What a top she was, fucking her bottom to completion twice without getting her cock out of my hole. Her penis may have been small but it was powerful for its size and she used it skillfully to dominate me and force me to submit to its strength and energy.

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    • #3
      ohhh sexy..

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      • #4
        Hot stories!

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        • #5
          Sexy beauty with great story.

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          • #6
            Lol, people like the stories but is it just me and xx6fallen6hero6xx who are the only bottoms here? I love being my girlfriend’s bottom.

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            • #7
              +1 trannies are the best oral lovers. I always prefer them over women. +1 trannies are the best oral lovers. I always prefer them over women. I don't know why they are sooo good, maybe it's the most preferable ask from their partners. As for being bottomed, I was thinking about it but have never tried it. I have experience with a dominant mistress, here's the site if you wonder nicolebdsm.com. But I refused to be penetrated with a dildo (she's not tranny). I think being bottomed with a real cock must be something super sensual. I wouldn't do it with a random ladyboy. Such sex must contain both physical and mental connections.
              Last edited by silentworker; 10-25-2021, 02:34 PM.

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              • #8
                Anal dilating kits are recommended by Goldstein. Dilating kits are essentially a collection of dildos of various sizes. Start with the tiniest toy, lather it up with as much water-based lubrication as you can, and then insert it into your body. You become accustomed to breathing with it inside of you. If you want more information to check out the websites https://disney-porn.com/.

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