Since I broke things off at the first date, I thought things would end there. Apparently Tim had different ideas. He kept starting conversations with me, both online and offline, and I kept responding. For a while I thought I had inadvertently friendzoned him. To be honest, it didn’t mind me that much as I liked his attention and I had been clear enough on my intention.
Our more sexual late night conversations continued as well. He kept praising my looks and handjob skills which flattered me. I didn’t see any of the shyness of that first date anymore and we actually got a bit flirty. When he praised the handjob he got again I told him that he didn’t had any comparison material, to which he reacted that I was the one who could change that. “Well, it would still be two handjobs from the same person. I can’t imagine it would make much of a difference.” – “You know I have no experience at all, I only know your hand. But I can’t imagine needing anything more.”. I know that was a cheesy and slimy line, but still it did something to me. It flattered me, but even more so I think it gave me reassurance. That I would be enough, even with my vaginismus. I hadn’t had a virgin in a while and I guess his lack of experience had the advantage of making everything I did being the best he ever had.
So I offered him a repetition of our previous experience, minus the uncomfortable date. This time no pity/consolation handjob but an actual one. He gladly accepted the offer and we made an appointment for the next day after classes. We biked to my room together, talking about all kinds of stuff and although our conversations weren’t sexually loaded at all, I thought I saw something of excitement in his eyes.
I wasn’t wrong. As we got to my room and I offered him a drink, he asked right away when we would start. “Inpatient are you? Go ahead, settle yourself on the bed then, but I’m going to drink first.” I took a glass of water and when I turned around towards the bed I saw he was already naked, sitting against the bed end with his penis straight up in the air. His penis was larger than the average one, almost beating my second boyfriend in fact. I didn’t care for that though, I only did handjobs and a smaller one, as long as it isn’t a micro, lies better in the hand. Easier to touch the right places and therefore easier to get off. But still, I could work with this.
“I can see you’re really excited!” I laughed to him while I walked towards the bed. “I see I don’t have to remove my dress to get you hard, that’s good to know”. I settled myself besides him and I could see he didn’t get that I was serious about that. I moved my right hand over his body and put my fingers around his shaft. I squeezed softly when he protested. “Aren’t you going to get naked?” – “Why should I? You’re clearly already aroused.” I always liked doing as little as possible to get a guy off. If his arousal did all the work that’s all the better for me. For me that, as well as the speed, was all part of the challenge. The fewer tugs needed, the more clothed I could be, the slower the speed of movement but the quicker the speed of ejaculation, all were signs of the guy being very aroused over me. I really craved that.
I started slowly moving my wrist up and down. “You don’t need more than this. You said yourself you only needed my hand. Prove it…” Again he protested, this time he tried flattery. “But you’re so beautiful, I want to see you.” – “Flattery isn’t going to help you this time. I know you want to see me naked, but you didn’t need that, remember? Just my little hand was enough.” I said while moving up the speed and grip in phases. I think he got the message at that point and he remained silent. “Good boy, just enjoy yourself. If you need to, you can always think back about last time.” I guess that worked as he started to breath more heavily. “You’re getting closer aren’t you? Just let it go, spurt all your little seeds in my hand. I guess you were right, my hand is all you need.” I waited a few seconds but still he held on. “Or do you want to see my breasts or vagina? What would you’d like to see?” – “Your vagina” he panted as he came seconds after saying that, overflowing my hand with his white fluids. “Good boy! See, you don’t need more than my hand! No need to actually show my body at all!” – “Shit… Fuck…” – “Why the cursing? Didn’t it feel great?” – “It did. A bit too much, I came way too soon…” – “Why would that be a bad thing?” I was serious. Like I said, I liked it when a guy was quick. Usually I told that before I started using my hand but I had a feeling beforehand that I didn’t need much this time and I apparently I got that right.
“I could hold it in for much longer last time, sorry…”. I got a bit mad “Did you hold yourself in?! What the heck for?!” I was insulted and although I knew more guys did that, I always wanted to discourage that behavior. “What do you mean? I thought girls liked it if you’re not too quick?! I practiced for that!” – “Well, this girl doesn’t. Why would I appreciate a guy taking forever and leading to more work for me? It can get tiresome you know!”. He looked a bit taken back at that. “Ooh…” – “What do you do to postpone your ejaculation?” – “Trying to think of different things, unsexy things” – “Why the fuck would you do that?! I’m doing my best here and you’re trying not to like it?!” We actually got into a bit of a fight, although Tim quickly bowed down. “Okay, okay, I get your point, sorry okay? But it’s not only that. I’ve learned from other guys in high school to edge when masturbating to prolong your stamina.” – “Really?” – “Yeah…” I originally planned to start giving Tim a bit of experience but now I started to doubt that decision. I didn’t feel in control anymore. I needed to regain it, even though that thought process was subconsciously.
“Look, I don’t mind helping you out more often and give you a bit of experience along the way. But you’ve got to get quicker. We can work on that together and with enough practice I believe you can get more like normal boys. But you have to start letting yourself go and stop edging when masturbating. Actually, let’s quit with the porn and try to ejaculate without. In fact, perhaps it is better if you don’t masturbate at all for a while.” Tim remained silent, seemingly in deep thought. I remembered he had feelings for me and decided to use that a bit. “You said you only needed my hand, right? Then prove it by not masturbating and I can help you twice a week as long as I see progression. If you get consistently under three minutes, you can see me naked again.”
Why was I putting so much effort in him? Usually when a guy didn’t fit, I would just end it and not have any sexual stuff with him anymore. For some reason I tried to make a project out of Tim. In hindsight I already liked him more than I wished to admit. – “Okay. So if I would cut off masturbation, you would give me handjobs regularly?” – “In the end, yes.”
Although this time he went home right after our talk, the next few times we met in my room were more like small dates even if we didn’t call them that. If it was later in the day I cooked for the both of us and we ate together, if we met earlier in the day (usually on Tuesdays when the classes ended earlier) we talked for a few hours or watched a movie together. That was always preceded by a handjob and to be fair, they got quicker by a lot. I think his lack of masturbation and stopping holding himself in played the biggest part in that. Where his first handjob took a long time, probably about 20-25 minutes, we got to consistently less than 10 right away. To drop that number even more, I tried my best to make them as arousing for him as I could and after a while I showed him elements of my body (in the end mostly my vagina and my breasts by removing my top or bottom clothing) which helped a lot.
Although the aim was to get below three minutes we only timed once in a while. I had a good feeling on what was a good and a bad session in that regard and that was enough for me. It wasn’t about the specific time, it was about getting him quicker, which ended up as a great challenge and project for the both of us. I’m not sure if he actually stopped masturbating and watching porn but I didn’t mind that much, as long as we had a great time together.
More importantly our dates got better too. Tim completely lost his shyness around me and I started growing fond of him more and more too. Our late night talks got less sexual, probably because he stopped masturbating during our chats, but more serious. Our values aligned and he was as much a participant in the conversation as I was. We started doing things together ever so often and started spending most of our breaks together.
Then I read about triggers. If someone would concentrate on a specific thing (an image, a smell, a sound, etcetera) when shortly before orgasming, that became something they got into and should speed them up in that regard. Think of it like Pavlov’s bell that made the dogs drool, except instead of making dogs hungry, I would make a guy horny. As he got a lot quicker over time, I started unclothing myself for the handjobs most of the time, even though we probably weren’t at the 3 minute mark yet. I told him about the trigger method and I proposed using my pubic hair/vagina as a trigger, as that was already a kink of him and it was something that he wouldn’t see out of a sexual context (as to prevent “accidents”).
As we went on for longer we also started differing more in positions. Instead of mostly sitting, we alternated by lying down or with me sitting on top of his legs. We even got to do it secretly at a few semi-public locations, in which his speed greatly helped in achieving that before anyone noticing. On rare occasions I blew him, especially to catch his ejaculate when we had nothing to clean with. But the biggest step was that I started allowing him access to my vagina so he could reciprocate.
I still was a long way from curing my vaginismus, even though I was now more motivated with my exercises with the prospect of deflowering him. Despite that I let him pleasure me orally, as the first guy in years. He did remarkably well for someone with no experience in that field and after following some instructions he actually got me to orgasm most of the times. It was a bit funny, while his times got quicker and quicker and I had to do less and less work, he started to spend more and more time on my pleasure. As the trigger method dropped him to around the 2-3 minute range, he licked me for 15-20 minutes after. The dominant side of me actually liked that.
Although I didn’t stop completely with the handjobs to other guys, it got to be less and less. We didn’t discuss exclusivity, I knew I was the only one for Tim anyway, and I liked that. Although I wasn’t telling him proactively about it, I wasn’t keeping it secret either. He often asked me about my other exploits during his biweekly handjob and when I told him about them, he got aroused over the thought ever time. Looking back it made sense towards the kinks he ended up having. That would be later discovery though.
After he asked me about our status and I admitted having feelings for him too, we made things official as being in a relationship and although we didn’t discuss it explicitly, I broke things off with other guys. As Tim became my boyfriend we were together more often and our biweekly handjob turned into a more elaborate sex life. Still, for him that was exclusively through quick handjobs, which were practical for me too. In previous relationships I had periods in which I was less in the mood, now that difference in sex drive was solved with a quick easy handjob that wasn’t so energy draining or time consuming. Sometimes at a party or when we went swimming, guys used to get overly attached, now I could just give him a preventive handjob before that. I was used on getting my way with my practical outlook in sex in general and handjobs in particular from my more casual encounters. Still I didn’t anticipate having it that way in a relationship too.
Despite all that, I kept being worried about my vaginismus and inability of having penetrative sex. He could tell me constantly that he didn’t need that, or want that, but only one small remark on his regrets on being a virgin brought me back completely. Then again, the vaginismus was probably the reason we could have it like this. Were other guys would have known what they missed, he only knew the difference between his own hand and my hand. It’s like most guys with anal: most guys have never had it and if you never had it, you don’t know what you miss. If you had it and you liked it, that can get a point of contention in a relationship if the other doesn’t want to do that. But since my new boyfriend didn’t know about the sensations of penetrative sex he already appreciated the difference in having a sex life to no sex life at all. Sure, he desired to stop being a virgin anymore but that was probably more of a guy insecurity than actually wanting to feel penetrative sex. Or than actually needing it. What if I got cured from my vaginismus, would starting to have penetrative sex actually be in my advantage? Why change a winning formula when we have it perfect the way it is? That got me thinking…
Source: reddit.com/r/sexystories/comments/uk08p4/my_boyfriend_the_virgin_part_2_how_a_hjfwb_grew
Love this, thank you for continuing.
Thank you for posting! Hot and wholesome, well structured and presented.
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