Monday, July 16, 2012

Deflowering a bottom virgin

This boy (ass to camera)  looks exactly
like the hottie 22 year old.
These pics from Horny Texas Fratboy show the body type of the hottest guy I ever hooked up with, described in this post. 

After my extremely disturbing hookup with Foot Fetish Guy, I  picked up the sexy 22 year-old who'd been messaging me.  He wanted some M2M action so badly and, for some reason, he decided his first time was going to be with me.

 "22, brown hair, medium build, not too hairy but love hairy men, had sex with women but never finished with a man. Would love to though.   Like men of all shapes and sizes.  hairy or not. Mostly older men "

He was standing out front of his apartment. Punctual! And hot to trot!! He was a beautiful, nervous young man... Since his roommate was in the apartment, we drove in silence to his parents' house who were out of town. He was soooo nervous and had difficulty looking me in the eye as we walked down to his old bedroom.

At my suggestion, we lay down in bed fully dressed and immediately went to it. Amazing, aggressive kisser with, pouty lips.  Flawless body;  broad, muscular shoulders, slim hips, lovely muscular thighs, perky little bum....

Sweet personality!  Aggression! Pent-up horniness! He wanted so badly to be with a man!! At my request, he allowed me to unbuckle and unzip him ..... like unwrapping a Christmas present. OMFG! The fattest, most beautiful cock ever,  cut but very smooth, with a mushroom head and the most amazing set of balls hanging beneath.   My cock worship went into overdrive!

We made out with increasing intensity as I ran through my usual repertoire and he followed eagerly. He had me squirming and moaning! At my suggestion, he straddled my chest (with me on my back) and thrust his cock into my mouth, gasping audibly as it rammed into the back of my throat.

He asked me to take his balls in my mouth, a first for me! They were so big!... his beautiful balls entirely filled my mouth and I run my tongue around and around and applied gentle pressure.... more moaning.   I was so uncertain as to much pressure to use....  but he was so vocal... much groaning & gasping in pleasure.

During my blowjob on him I stuck my lubed finger up his ass (with his permission) and he rammed his ass repeatedly down onto it, I thought, "Oh my God, his ass is hungry for it!" Sure enough, he groaned, "I want you to fuck me!"

He found a condom and put on me with his mouth (clever trick) and tried to lower himself on to my cock, with me on my back.   After much effort he said, "I can't do it, you'll have to loosen me up a bit more." He went on his hands and knees with his asshole pointing heavenwards. With much lube and one finger, then two fingers, I got my cock in and pumped his virgin ass.  Wow!

After a minute or less I went a bit soft, probably the combination of his moans of pain, I think, rather than pleasure, and the unexpectedness of being asked to top for the first time.  I was thinking, "OMFG!  My cock is up his asshole!!."   And another turn-off was the fact that .... er... he wasn't particularly clean down there (Ewww!) and we were doing it in broad daylight, although his hygiene and grooming was perfect in every other respect.

We were together for nearly 2 hours, the last 30 minutes we lay together, limbs entwined, bodies glistening with sweat and (I think) he fell asleep.   Sweetness!  I could not resist running my hands all over his body, up and down his lean, lightly furred torso, around the delicious curve of his ass cheeks, up his inner thighs.    I had to tear myself away to pick my kids up from work.

He's messaged me four times since our encounter, actively planning the next.   He asked me, in the politest possible way, if I would considering bottoming for him. .... I agreed,  but as I posted in A Reluctant Bottom,  I need to do some advance preparation first.  I'm a bit apprehensive about it....


  1. Ihave got to stop reading you just before leaving for work. Now I'll be horny at work. LOL

  2. Sounds like you both had a good time. However, the things he asked of you (lube and finger work) and ability to put a condom on another man's dick with his mouth would hardly justify putting him in the virginal or inexperienced category. Still you both could learn a lot from each other in this situation. Enjoy.

    1. I agree with you; I had my doubts about his inexperience. I did ask him if he really had not done anal before. He swore that he hadn't and I believed him. Maybe his "experience" came from a watching a lot of porn.

      I apologized for getting soft and he said that it was probably for the best as he was really uncomfortable when my cock was in his ass.. So I do believe he was a bottom virgin.

  3. Wow! That was really hot. I'm with skier.

    Hope this isn't the last time you guys get to play around.

  4. Probably the two most important things for any virgin or inexperienced bottom is a ridiculous amount of lube and a lot of time.

    The reason he was in pain was because he was not relaxed. Proceeding at a snail's pace is the best way to relax. As for cleanliness, a good bottom uses an enema in advance. By all appearances this kid will be spending a lot of time on his back with his feet in the air so he might as well learn how to be appropriately prepared sooner rather than later.

  5. What a wonderful experience for both of your despite some of the issues that came up. He is clearly so eager to learn and explore his own sexuality, and in doing that to get you to do the same. You can clearly excite one another with your moves, and now you can add some nice verbal cues. The passionate kissing that goes along with the sex can be such an amplifier - go for it and it will take you all kinds of places! I have been following your blog a long time and am linked to you - and wish you the very best in this whole new world you are entering.

  6. Thanks for commenting, everyone! It was my sweetest encounter yet! This sexy guy was not very talkative (the 'strong, silent type', not uncommon among young men.)

    After our encounter, He was laying back on the pillow, spent, eyes closed. I asked him, "Do you think you are attracted to men?" He response was gutteral, almost a growl, "OH....YES!!!"

    1. I hope he doesn't take the route we took. Accept himself now rather than later.

  7. with a boy that looks like taht and such a hot body-i think i would have loved to rim his asshole for him as dirty as it was;0.......


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