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    Losing My Oral Virginity

    Although it was a new experience for me, the same couldn't be said for him.

    After many, many letters between us here at IF, we decided to take things to the next level.

    We were both cock-hungry, and our letters just seemed to make us overly-anxious to experiment with each other.

    I felt I could trust him, and, I suppose, him, me.

    We agreed that meeting in the city at a hotel would be the best way to achieve this, which was OK with me.

    When the day came, he arrived before me and waited on the 5'th floor (in room 517.)
    I called and told him to take a shower as I would soon be there.
    I didn't really like his idea of showering together, as I didn't want too much contact (except with his dick, that is.)
    I didn't want any type of closeness or hugging/kissing, which he seemed to not be averse to.

    As I rode the elevator up, I said to myself 'I hope this is a safe encounter.'
    (Even though we had met once before, you never can tell what can happen, especially where sex is concerned.)

    An important consideration for me was to film the encounter, or not.
    I thought it important to have a record of this afternoon for me to reflect on, and also to masturbate to if it were at all hot.
    Because I didn't want to be recognized, I mentioned maybe wearing a mask would be an option.
    K told me about a tgirl he used to play with that always wore a mask and put her hair in pigtails, which he would grab when he face-fucked her.
    As I have long hair, this sounded like a good direction to go in; but in the end, the light in the room was so low, I looked like a silhouette anyhow.
    (I'm very glad I made the decision to capture it, though.)

    When I got to the room, he left the door unlocked and was lying on the bed.
    I was glad to see his erection forming a tent in the bed sheet.
    We both nodded to each other, but said nothing further.
    I decided to just strip right then and there, as he was already naked beneath the sheet.
    (I was so psyched-out, my heart pounded in my chest and mouth, and I thought nothing of embarrassment.)
    When I took off my jeans, my cock flopped out, as it was already hard; so it was evident we were both excited to see each other.
    I walked over to the bed and, without words, he grabbed my hand and pulled it to his cock.
    It felt like such a release to finally feel it - a fantasy I've had most of my life - like the beginning of an intense journey soon to occur.
    His cock felt better than I thought; long, yet thicker than it had appeared in the photo.

    It is an odd sensation, as when we touch our own cocks, we feel the sensation at the same time.
    When I touched his cock, I felt it in my hand, but the other side of the equation was missing.
    It felt like a rigid muscle (which it is) and kind of like a snake, ready to strike.
    I was initially afraid to bend it too much one way or the other, but saw after a while it was very resilient.
    I really got off on jerking him off; it's a powerful feeling; controlling a man through his cock.
    (I can now see how women get their way most times.)
    I was thinking of jerking him until he orgasmed, but thought better of it, as I wanted his cum on my face.
    I took out the lube I brought with me and applied just a bit of it to his cock, and also his balls.
    (A nice surprise was how nice his balls felt in my hand; a nice diversion from the hard cock.)

    He then pulled off the sheet and yanked my head down on top of him.
    I awkwardly hit my eye with his stiff dick which caused me to see stars.
    I thought to myself 'what a way to start a fantasy!', but quickly forgot the pain/embarrassment.

    I stuck my tongue out and began to lick the head - the taste was neutral, though maybe with a slightly salty tinge.
    We agreed on a certain amount of 'dom/sub' interplay, though I strongly stressed this was not to be too intense.
    (In fact, I told him if it did escalate in any degree, I was out of there.)
    I mention this because what he did next was to push me away, jump from the bed and order me to do the same.

    He then pushed me down to my knees and thrust his cock into my mouth and started pumping intensely (fucking my mouth, if you will.)
    Suddenly faced with reality, I was a little afraid of the size of his cock; I really thought I was not going to get all of it into my mouth.
    I did my best to keep control of his member, but there were times where I gagged when he went a little too far down my throat.
    (I've had a little practice with deep throating, but this was something else altogether.)
    I really got off on the idea of me giving him a no-hands-blowjob; something I enjoy when watching porn.
    It was such a great feeling to pleasure him with only my mouth; my hands grabbing the backs of his legs while he pumped in and out.
    This continued for some time, as I could see he was enjoying it very much and I wanted to please him.
    A nice touch was that he produced a nice amount of pre-cum for me to enjoy.
    They say this can also contain questionable content, but I decided to throw caution to the wind and lick and suck this sticky fluid.
    It was a nice thing to experience, as it's rather rare, I believe.

    At one point he wanted to open the blinds and have me suck him off in full view of the city.
    Although this can be a turn-on sometimes, I decided against it as I didn't want to call too much attention to ourselves our first time together.
    (Besides, we were only on the 5'th floor; hardly a beautiful view.)

    While looking towards the window, I noticed one section of wall covered with mirrors.
    We moved closer so I could watch myself as I gave him oral; which excited me to a fever pitch.
    One thing I wasn't prepared for though, was how unattractive I looked while doing so.
    It looked to me that my mouth was in a distorted shape as I tried to fit him inside.
    I instantly attempted to work on this so as to appear at least somewhat alluring; to him and me both.
    (This is something I definitely have to work on if I try this again in the future.)
    Girls have no problem as they are beautiful to begin with and have delicate, sensitive mouths.

    In one of my e-mails to him, I mentioned a long-held fantasy of giving a bj while lying on a table and having the cock fed to me from above.
    He loved this idea, and also suggested I wear lingerie while doing so.
    This I wasn't into, as I tried it a while ago and didn't think I looked very appealing (too hairy.)
    He mentioned this and asked if I were willing to give it a try.
    There was a writing desk in the room, and climbing on top, I laid down, facing upwards.
    He walked towards me with that raging hard-on bouncing as he came nearer.
    He bent his cock down into my mouth and I started licking and sucking him.
    Luckily the desk was near the right height for us to perform this; maybe a little low, as he is tall.

    A new experience was his balls hanging down for me to explore.
    This turned me on even more than his hot cock.
    I started to lose control as I licked his testicles because it was something I was not expecting to do - which is always a turn-on for me.
    I loved this as his balls seemed to balance the spear-like hardness of his shaft.
    Curves and hard, straight lines - like yin-yang.

    He then told me he wanted to put his cock inside me, but we had already discussed this was not an option.
    (Thank God he was not that much of a Dom, as I would have had trouble walking home.)
    (I do admit, though, that at that point, I was so excited and almost to the point of losing control that I probably would have done anything.)

    When it came time for us to cum, I was very excited, as this would be the culmination of all my long-held fantasies.
    Our previous agreement was for me to jerk him off into my open mouth, but I didn't feel safe swallowing his sperm, even though we had both been tested recently.
    I thought a good idea would be to ask him to put on a condom and fuck my face until he shot his load.
    He asked if we could forgo the condom, and would I jerk him off onto my face?
    This excited me - the thought of his hot cum spurting onto me, so I told him it was OK.
    (Though I had to remember to keep my mouth shut.)

    I jerked him for only a few minutes, as he was very horny, which was nice, as I didn't want to be wanking someone for ages before they came.
    I really liked jerking him off onto my face, but in the heat of the moment, I yelled for him to jerk it himself, as this was hotter for me - to have him use me as a receptacle for his sperm.
    He also liked this idea, because he started moaning for only a few seconds before saying 'here I cum, here I cum!'
    I thought to myself 'this is the moment I've been waiting for for a very long time!'
    In a very hot move, he backed up a few steps and pointed his cock towards my face and blasted an impressive cumshot.
    I loved this; my favorite part of sex in the videos I watch, and to have it happen to me in real life was beyond words.
    I counted the spurts - I think there were 7, but the first 3 or 4 were beautiful; semen flying in graceful arcs before landing in stripes on my face.
    When it hit me, I was surprised at how warm it was; somehow I thought cum would be cool, but that's not the case - it's actually hot.
    I have to admit, I did open my mouth without thinking and tasted it as it trickled down my cheek.
    (It was pretty salty, but not unpleasant.)
    Though I then quickly came to my senses and closed my mouth.

    As he fell on the bed, I went to the bathroom to clean up, but wound up staring at my cum-streaked face in the mirror for quite a while.
    I looked into my eyes and really felt a great relief at what had transpired, as this was literally years in the making.
    I thought of taking at least one picture as a souvenir, but didn't want to risk having something like that on my phone.
    (Besides, his cum was starting to become watery and fall to the floor.)
    But before washing my face, I rubbed it in like a beauty cream, just because I thought that was a somewhat nasty thing to do.
    (Though some do extol it's medicinal virtues.)

    As for me cumming, I didn't want him to return the favor.
    I preferred to masturbate myself while I sucked him off again.
    We returned to the desk with me taking his cock from above.
    Though his cock was drained, it was still swollen; maybe more so than before he came.
    After only a few seconds, I gagged on him as I shot my load high into the air; maybe just as impressive as his performance had been.
    (Looking back, I should have taken it a bit slower, as I really wanted to savor the experience.)

    After this great time together, we decided to take a break for a drink in the hotel bar.
    We got dressed and headed downstairs.
    This was a waste of time, as after only a short time talking of what happened, we both had raging hard-ons once again.
    (I guess it was the newness of the situation, like when you have a new girlfriend and you both can't keep your hands off one another.)

    So it was quickly back to the room to have another 'go' at one another.
    This time the sensation was even stronger than the first time (at least for me.)
    I stopped him when he started to get undressed.
    I liked the idea of me kneeling before him with only his cock sticking out through the opening in his jeans.
    But I took off all my clothes, as this has always been a fantasy of mine; to be naked and submissive, while the other person is clothed.
    As I started to suck him, he got so hard it was painful to see his cock straining through the small opening.
    I told him to unzip and let his cock out so I could work it better and also massage his balls.
    I gave him the best blowjob I was capable of, but only for about 5 minutes.
    Then the most amazing thing happened:
    He started to moan and lose control, as I could hear him almost choke and gulp on his saliva as he was mouthing his words.
    I could actually feel his balls tighten and see them retract up into his body.
    When this happens with myself, I know it's going to be a very powerful orgasm.

    I still have misgivings about what happened next, but you can't change the past:

    The situation got so intense, I tried to push his cock further down my throat as I could, and keep it there.
    I had done this before, but always took it out quickly, as you can't breathe when it's lodged in your throat.
    He then seemed to really get into his 'Dom' persona, as he grabbed the back of my head and held it there so I couldn't back away.
    I started to panic, but thankfully, his utterances rose to such a fever pitch, I knew he was going to cum in a matter of seconds.
    And I was right - with his cock down my throat, I could feel his balls throb with each spurt.
    It was an odd sensation, as I could sense his cum was shooting straight down into my stomach, but couldn't really feel or taste it.
    All this time, I was breathing through my nose, relaxing my gag reflex and trying to keep calm.
    While he was cumming, I was so excited, I also ejaculated hands-free, as my hands were around his bottom.

    He fell backward and he released his grip as his cock pulled out from my mouth.
    As for me, I just laid on the rug and saw stars dancing around while the room went dark.
    (I think this was for lack of oxygen, and not a very smart thing to do to oneself.)
    I thought to myself 'what did I do, why did I swallow his cum?'
    Dangerously, I often seem to throw caution to the wind when in the throes of sexual abandon.

    When I regained my composure, I joined him on the bed; where he looked at me with concern.
    He said 'sorry I came without the condom' but I didn't feel too threatened as we had both tested negative for any sexual diseases.
    I did feel rather queasy though, as I suspect sperm will do if ingested.

    I did make an attempt to clean up the room a bit, as there was sperm and saliva over most of the bed and floor.
    I tried to spare the maid this messy job.

    Afterwards we talked a while, though I did feel somewhat awkward sharing such an intimate part of myself.
    Yet I did feel I had met a friend; this friendship where we could explore our fantasies.
    It really does take a lot of trust to achieve this.

    It was a little sad though, as he was to move away in the next 2 weeks, and this was the only time we had before then.
    I can always visit him, or him visit me in the future, so it's not over for good.

    It was something I will never forget, as, in a way, it's like losing your virginity all over again.
    With me, it was my oral virginity.

     
      Posted on : Sep 1, 2022
     

     
    Add Comment
    rebop
    rebop's profile
    Comments: 875
    Commented on Sep 3, 2022
    thanks for sharing your story. i am enjoying reading it while i masturbate. it is giving me a nice boner reading about all the different ways you sucked your friends cock and enjoyed playing with his balls. i looked at your pics too. you have a very sexy cock
     
    LuvsToes
    LuvsToes's profile
    Comments: 1,089
    Commented on Sep 2, 2022
    loved reading this, would also desire to reciprocate similar events with you should the opportunity ever arise.
     




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