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Thread: Three First Times

  1. #1
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    Default Three First Times

    Just posting a bit of a ramble,

    I have been with three girls, and heres the stories

    I consider myself a guy with a high libido, I've always loved women and was introduced to porn and masturbated from an early age. Eventually I became more and more aroused as I came across the trans images and videos, eventually finding advertisments in backpages of newspapers and found that there were actually girls like this who exist I could share time with and explore this side of me.

    It must be close to ten years now, but I took my first chance. Late at night, calling up Lucy and seeing whether she would see me. A little light flirting on the phone and explaining my reasons for calling, she agreed to let me come see her at something close to 2AM as i was at that time and away I drove into the city. I don't remember parking, or how I got into the building, I was nervous, anxious, it felt like this might be a bad idea. There was someone in the hallway to the apartment who looked strung out, with long blonde hair, not like the picture- I was thinking oh my god what did I do and was worried then suddenly the apartment door opens a beautiful woman ushers me in and my nerves subside.

    tn_lucy10.jpg(Large Pic)

    We got into small chat, but it was hard to focus on anything but how good she looked. Something of like a housecoat and a bra panties, she was playfully touching and talking with me. I knew what I came for, and with little hesitation, we began the session with some deep french kissing. I moved my hand towards her face and down her body, slowly made its way all over her curves until her panties - and cupping the area with my hand, my first time touching anothers, she asked if I wanted to suck each other, I nodded and then she unrolled two flavored condoms, one for each of us and we 69 like a couple of vacuum cleaners attached to one other. This was a passionate affair. A little bit off and awkward with the rubber feel but none the less, theres something magic about being locked mouth to cock with another in a sexy ouroboros. She asked if I wanted to fuck her - I nodded again. She comes overtop of me as Im on my back, grabs my cock and begins the expedition for the hole (one of my favorite parts of sex is when the lady does this). I tempered her expectations, I was a young man, I have only about a 6 incher, I was like, I don't know, maybe its not going to reach in this position or work - she laughed and dissmissed me still holding my dick against her puckered asshole and suddenly glory glory hallelujah I was in. Ass feels different than pussy. A little tighter.. I dont know what it is, but that ring around my shaft and going in and out as our bodies grow tighter and closer, our balls patting one another like little high fives , and the kissing... I am a bit of a romantic so once the kissing is in the mix, its basically like being on a drug trip.. we had sex like this until I came. I didn't get her to, or ask her either. I was nervous, unsure about everything and after I came and we cuddled and it was close to 5 AM I had to get going. Our small talk was good and I fell in love with her of course haha.. I would never see her again, but I dreamt and jerked off about it all the time...

    This being my first time, I know I wasn't exactly feeling comfortable. I had a bit of a gag reflex, the rubber feel, not knowing my way around the tool, I just wasnt super sure on what I was doing, and although nothing was communicated like I was doing it wrong, there was no take charge out of me, and she was treating me as a delicate first timer. I knew there was more I needed.. which brings me to 'first' time number two... (After I play squash I'll get back to continuing this)
    Last edited by miketobias; 12-02-2018 at 07:22 PM.

  2. #2
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    Sounds like your first time was incredibly memorable. Thanks for sharing.
    I look forward to reading about your other experiences.

  3. #3
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    thanks for the positive comment! I am wondering if its therapeutic for me , or just making me edge closer to a relapse, I get a little bit of both feelings. It helps me to get some of it out there because its just pent up inside, but also reminds me a bit of why I came there/here in the first place and makes me question - well not question, but I guess just can't help certain things..

    So my first time was awesome! I remember leaving thinking wow what the fuck did I just do, and crawling into bed just before sunrise and thinking uh oh, that was really just the hottest thing I ever done and I don't know if I'm finished yet.

    so queue three years later or so and relationships have failed, and I find myself going back to lucys ad frequently to recollect in my memory and masturbate more and more frequently. I start thinking i could have any girl really, why not try someone new and begin to read in these forums, deep diving on the reviews and who would be a good service provider for the still relative novice in me.

    in scoping through ads, I hone in very quickly on one Tania Tequila - Tila Tequila was always so sexy to me, but here was not only a knockout that resembled her but the feminity radiating off her adverisement photos was incredible. She also had a quick video clip and at the time I was really nervous about some of the reviews I read, so figuring the video was pretty conclusive that this girl was real - slowly began building the idea up that I should go for it.

    tn_taniatequila16.jpg (Large Pic)

    One night me and some of my friends ended up going to the bar and doing some partying, its xmas eve-eve, got into a little cocaine and later that night we're combing some ads and talking about getting girls over. My mind can't get Tania out of my head.. If I show them her, they will want her - and if they want her, and look into her or try to interrupt my session - they are going to find out i have a bit more sophisticated tastes.

    We call some GG service providers over, and my mindset is after I cum I will shake this feeling. My session was complete. Standard condom sex with a female, pretty good, and gave her a good time - but where was the dick for me to suck? I wanted a nice tight butthole, and have I mentioned I COULD NOT STOP THINKING ABOUT TANIA. My friends are still over but I can't get her out of my head, I go to the washroom and see her ad had been updated and its 2am but if shes up I need to see her. I call and she answers - my heart is pumping.

    We talk, she's up still, I'm about 50 minutes from the city at this point but ask if she would be willing for me to come by because I haven't been able to stop thinking about her. She laughs and asks me how big I am - I say, 5 or 6 if its really going well - and like I am clueless she laughs and goes "what?! lol, omg, i mean like muscle" - oops. lol. I give her my build details and send her a pic of me at so she can see what I look like at that moment and we hit it off - later bros - I gotta go - and off in a cab flirting by text as I run fast as I can to what is by far the best experience I think I can ever imagine happening.

    tn_taniatequila20.jpg(Large Pic)

    I get there, buzz in, but can't get an elevator to come down, I ring her and she comes to the lobby to meet me - I get in and we're the only two people there which works nice because shes in a long tshirt nighty just busty and beautiful and we start making out the elevator ride up. Now I don't think I'm doing any disservice by being honest with what happens next - at the time her ad was very clear that she was a party girl and I was honest to her about what happened earlier that night and what I was on. I did however say it was not my first time. She did not seem to believe me, I guess it was my passion and non timidness. So when we got in the door and the next thing she said was "I don't want you to get soft, we fuck" and I looked her up and down and replied, "there is no way I'm getting soft with whats in front of me right here" and I took her night shirt up slightly revealing her member and kissed it softly her putting it into my mouth. My first bbj and exactly what I craved the raw sweet taste and passion of sharing something so intimate just releasing so many endorphins and adrenaline - she pulled me up to kiss more and then returned the favor - hard as a rock and throbbing in her mouth now, I received my first bbj and it might have well been like we were fireworks from that moment on. Next she asked if I would take a viagra, I agreed and we tore up the sheets for hours. I never bottomed in the session, but for hours and hours we fucked and sucked and came and came - the kind where you go to get water still fucking, bring it back and drink it while still fucking, just could not detach - it was unfuckingbelievable and a little afraid now that it ruined me - as I kinda need a girl like that haha. I remember it was like 7 am and we hadn't slept yet but I needed to catch a go-train back to my place and I wanted to sort of do it before anyone woke up and asked too many questions, it was xmas eve now after all. Before leaving making small chat in the washroom I just asked if I could suck her cock and jerk off once more before I left - started doing that and shortly into it she put me inside her ass again and let me finish proper and intimate while lip locked too.

    I left with my head spinning again, going a bit deeper, but still not feeling yet like totally finished - I heard alot and had been interested in being penetrated. we explored with some fingers which felt nice but I had some sort of 'dignity' about my virginity hah, that I sorta thought if it happens for me I don't want to necessarily also pay for it, I mean Im giving up my butt virginity - it should be a mutual thing maybe. I fantasized about meeting a girl at one of the clubs around toronto and hitting it off and being able to replicate a passionate real intimate night but go further - although I dont think that will ever happen, I do get a little bolder some nights and really consider it.

    Since then I had been able to feel pretty satisfied - it was un-real. No intimacy - fuck session, no intimacy ever short of finding a girl just like tania and doing everything me and her did together will probably ever top that night. It was very carnal and hot and although I wanted more, without connecting and hitting an amazing win by the girl being as cool and passionate and into me as what happened my first two experiences, it was enough for me to call it a day and believe that I wasn't going to need to try and jynx this by throwing the dice again...

    But then about 2 years ago, after a bad breakup ( a terrible catalyst I know, but love hurts) I am on tinder and I connect with a girl who explicitly in her profile mentions she happens to be my type. We connect, chat, video chat, are flirty, and after a week or two she is sort of flirting a bit heavier and sexting with me. I am seeing things I have dreamt about.. But I am hesitant to pull the trigger too quickly, because its kinda real, we're flirting, I dont want to one and done, maybe we can date if I play it right. (Or was it ever going to be possible? but thats another story).

    My attempts to ask her out a few times a few places are not too well received, maybe there are other guys, we talk less as it fizzles out and I found myself back online and looking into again what excites me... some of the same girls are around, but also, some new beauties approach.. things have changed like crazy..

    Andrea Mendes...

    tn_andrea_mendes21.jpg(Large Pic)

    Dita Dior..

    tn_ditatg21.jpg (Large Pic)

    Amber Kane

    tn_tatyana12.jpg (Large Pic)

    Gina Ferrarra,
    tn_ginaferrara20.jpg (Large Pic)

    Jade ...
    tn_laylabomb26.jpg (Large Pic)


    Kymlie,
    tn_katia8.jpg (Large Pic)


    Kimberly,
    tn_kimberly10.jpg (Large Pic)

    Lola,
    tn_lola_5.jpg (Large Pic)

    Indiva,

    tn_diva23.jpg (Large Pic)


    Angee,
    tn_angeediamond5.jpg (Large Pic)


    ZARA

    tn_zara_ts9.jpg (Large Pic)




    And Soo Sooo Many More! All of them! I am in love. Holy fuck they are all incredible now. (not all these girls were available at the time psa)

    Eventually I study up more, I narrow down the list a bit and because I am spoiled from my first two sessions, I really want to try and choose right. I am thinking I might actually try get a lil bit of the action going both ways this time and see if we can make something new happen for me. I begin getting excited at the possibility of Lexi - shes in my area, and shes inked, just drop dead gorgeous. A dom, but supposedly sweet- maybe she could work me in a bit with some toys, given her reputation on the member it might be difficult to make that work on my first session. I call her up, heart is racing, explain what I'm sort of looking for but it ends up being kind of a bad timing. I was hoping for an outcall. I wanted to be in my comfort zone, I felt like maybe since its a premium price as well that the girl will also be less clock watchy because you're pretty much taking 2 hours worth of the rate or more for the luxury of a one hour outcall. In my head it all made sense. But she's unable to work it out. Im nervous as shit and getting worried about maybe I should call it quits while I'm ahead. 2 girls, 2 amazing beauties, 2 incredible times.. but I can't shake it.. I'm hurt. I want some love. I earned it. I worked out alot, I was eating right, I was being good to everyone, it was time to treat myself. I go back to the board and decide to go for it again and roll the dice with Adrianna Fox..

    (sorry for the rambles, was gonna be this, jerk it, or submit to calling up one of these lovely ladies, but I'm trying to avoid it)
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    Last edited by miketobias; 12-02-2018 at 08:02 PM.

  4. #4
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    If I remember right from others post Kymlie is post op so no cock to suck on !

    Andrea Mendes would likely be my pick from the list u posted as I never been with her but would love to ,Lola would be a top pick as well based on reviews and pics . Been with ZARA and Gina , had fun with both !
    Last edited by Jake163; 12-03-2018 at 10:51 PM. Reason: Typo

  5. #5
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    Also just to mention Indiva looks really good but has consistently bad reviews with her level of service

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    I feel what would be the most therapeutic method to help you, while being undecided at this time for the search of your third encounter you just need to close your eyes and picture that your already with me and the rest will all come together.

    Thankfully for you November is over and you can now be able to jerk your Cock and cum to release all of that tension everywhere.
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    *(416) 821-2114‬
    http://www.tsdita.com
    Canadaís Shemale Pornstar

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    Oh Iíve pictured us together a thousand times at least, and there is an energy drawing me to you that I can no longer fight. I must have you. before the end of the year, I will enter your rear. Iím not jerking it til we meet either. Iím saving everything until our session.

    Have a great day beautiful

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