Since people have expressed a genuine interest, I felt it was time to finally break down my week for all of you so you can see what I was going through and how it all worked out in the end.
It started with my lovely Venus going out of town for a couple of weeks after having already been away from me for a week (she lives far away, is married, and has more of a life than just me). While I had gone a few months without a partner before we started hooking up, once I had her it was hard to go back to no sex. Plus we had only just finally transitioned to bareback that last time before she was away, so it was even more of a tease.
While she was away we discussed timing and worked out that her cycle synced up well with her return. Not quite well enough for either of us to take the risk of a creampie (despite how badly we both wanted one), but well enough to take the much lesser risk of an anal one. Which would mean our first anal bareback. We were both extremely worked up about this idea, and I suspect you may have seen some of our pictorial conversations in reblogs on here.
The week before her return I got the idea to refrain from orgasm until I could fuck her ass. Not masturbation, but orgasm. I figured I could play with myself as much as I wanted, but I’d have to stop before I came each time and save it all up for her. It was my deviant form of a romantic gesture. And while she didn’t ask for it, she seemed to get a kick out of the idea.
Meanwhile I’ve been talking to a follower of the blog who recently emailed me to let me know she’ll be visiting my area next year and would like to meet up. While we’ve talked about a variety of things, obviously our shared love of sex (especially oral, in perfectly complementary opposites) became a primary topic and I din’t have to do much to get her to send me some dirty photos in exchange for a few improvised literary fantasies to get her off.
So when I got this new idea to save myself for Venus, I clued in my follower and let her know how easily she could frustrate me that week by sending me more pictures, nasty words, etc. And she took to the idea gleefully. Her competitive streak came out, and she clearly took the bait to try to break me. She sent many photos, including one that covers a kink I usually have to do some work to get, and each night I used those pictures to take myself to the edge. And when I say to the edge, I mean a new tip of the edge I’ve never found before, barely preserving my state with pulses and pre-orgasm sensations. One night a single touch of my cock would have set me off had I made the mistake.
She wasn’t all that had me edgy. Venus herself did a fine job of keeping the thoughts and text going and had me edgy as well. My cock ended up in my hand during more than one conversation with her, and one night that I almost managed to go to bed without taking any risks ended up in a chat with her that got me horny enough to find some erotica that took me so close that literally after pulling my hand off my cock and continuing to read I found my cock progressing into stronger pulses on its own. A few more words and I would have cum without touching myself. Again, I managed to shift my focus and throttle back in time, but only barely.
By the end of the week I was in pretty rough shape, and my mystery follower promised to make it harder on me by sending a video. She didn’t say what to expect, but considering how much damage the photos nearly did, I was a little concerned. So was Venus. Even though this wasn’t her idea, the idea of a girl halfway around the world breaking my plan to fill her ass to the brim with cum had her pretty pouty. And I’ve got to admit, that rivalry had me pretty turned on, too.
On Saturday I awoke to nothing specific, but hornier than ever. I stroked myself to within a few seconds of orgasm, but managed to shut off before heading out for a busy day that would hopefully distract me enough to make it through to Sunday when Venus would arrive.
And then I got the email from my follower that said only the following:
I’m going to break you later this afternoon.
I have to admit, that’s one of the hottest things I’ve ever read, given the context, and it put me on overdrive. I told Venus about it, and she began to worry, too. And while I had a busy day and very few opportunities to be somewhere I could get off, I knew it wasn’t impossible if the right evidence arrived.
By the time I was in my car headed to my party that night, I found myself in the most physically frustrated shape I’ve ever been in. My cock was so sensitive and so tense that it almost hurt, and it wasn’t even hard. I felt like if I moved wrong I’d cum. I knew I couldn’t hold out much longer, and I hadn’t received the video yet, and I was definitely freaked. I wanted to hold out for Venus, but the frustration and the tease and the game of chicken with my orgasms was too much fun, and I knew if I got that video I couldn’t hold back.
I told Venus all this and she begged me to wait to watch the video once it arrived until she was with me, until after I’d cum in her ass. I promised her I’d try, but that I was beginning to wonder if I could hold out even without it. And that’s when she decided to skip her plan to drive out the next day and would instead drive up that night, and meet me at midnight and give me her ass. I warned her I would’t last long, but that I’d probably be ready for more soon. She didn’t care. She just wanted to feel me cum in her ass. And so did I.
With that I went to my party and had a fantastic night that took my mind off of things for the most part. My cock calmed down and I had fun. And then I got the email with the videos. It took all my strength, but I held out and didn’t watch them.
Venus beat me home, but not by much. I came upstairs to find her sitting on my bed, and I promptly threw her down on her back and embraced her lips with mine as I ground myself against her crotch until I was fully erect, which couldn’t have taken long. I yanked down my pants only as far as was necessary, threw up the bottom of her dress that she had worn to the wedding she had attended earlier that night, and plunged my cock into her cunt balls deep on the first thrust (she was very wet).
I fucked her hard, I fucked her deep, and I fucked her fully dressed. My stamina was apparently fully under my control despite the week, and I got to ride it out until I was ready to shift tactics, get out the lube, and lube up her sweet little asshole while she rubbed her pussy to yet another orgasm.
Once she was ready, I carefully slid my cock into her ass. She was so desiring, and I was so desperate, that I think it took only three strokes before I had bottomed out, bareback, in her ass for the first time and began to buttfuck her in earnest, with strong, full strokes, slowly ramping up to the speed and strength with which I’d normally pound her pussy. And like my good girl she took it with only the most desiring looks on her face.
Finally when I told her I was ready to cum she began to beg me to cum in her ass. What I love about Venus is that she meant it. She didn’t merely want me to make myself happy, she deeply wanted my cum in her ass. As much as I wanted to put it there. And when I was fully convinced of that, I rammed my cock as deep as it would fit and unloaded blast after blast after blast of my hot cum into her and watched the reaction on her face as she felt me filling her up.
We kept my cock in her ass like a cork for as long as possible, and she kept my cum in there for quite a while longer before we finally called it a night and passed out in each other’s arms.
Sunday morning started out with Venus being awakened by my cock fully penetrating her apparently already-soaked pussy which led to a session ending in her swallowing my load like the good girl she always is. Less than 30 minutes later I was back in, fucking her from behind and finding my edge once again, pulling out only in time to cover her ass with what was still a surprisingly large amount of cum.
We fucked throughout the day in various places, on various things, and against various walls. She sucked me, I ate her, fingers, hands, tongues, etc. were all employed. She came many times, I held out to make sure I’d get it in the right place at the right time.
Our evening culminated on the couch, watching TV, when we forgot about the TV and she ended up back on top of me and began to ride my cock, bareback, in her pussy. The tone was different, and there was a sense of desire in both of us. She wanted me to cum again, but she didn’t want to pull off of me. I could see her doing math in her head, but we both knew we couldn’t risk it. But we also knew we could’t stand to stop. She wanted to feel my cum in her pussy as badly as I wanted it in there. She began to warn me that I was going to have to stop her before it was too late, because she wasn’t going to want to pull off. She rode me until I knew I couldn’t last much longer and I had to shove her off. She grinded my cock with her pussy for a while while we talked about how badly we wanted to push our luck, and I finally told her I was ready for round two of our little game of chicken.
This round didn’t last as long, and the stakes were higher as both of us were having a harder time fighting it. I finally managed to shove her off, but with a much closer call and a lot more resistance from her.
We talked as I came down from the edge and formulated a new idea. She wanted to fuck me ‘til my cock was good and wet with her juices and until I was truly at the absolute end of my limits of control and then, when I definitely couldn’t hold back the cum any longer, I’d pull out and shove my unlubed cock straight into her ass to finish. In all honesty, it was a stupid, reckless, dangerous idea. And I agreed to it wholeheartedly.
Round three began and I worked my way back. I knew I had to time it just right because too early and I’d have to fuck her unlubed and risk some serious pain. Too late and she’s have a pussy full of cum. I fought and held and finally called it at a moment that by a complete force of sheer luck was right on time because as I shoved my cock up against her asshole I started to cum, and realizing the risk I slammed her body down and felt my cock slide deep into her as I came for all I was worth. I didn’t honestly at that moment know WHAT hole I was in, but I was in, and it was too late to stop it and we might as well enjoy the ride.
Once my orgasm subsided she confirmed that I had found her ass just fine and my cum was deep inside it. I was relieved and exceptionally happy. She was in pain and just as happy. But I think the timing of my orgasm as the head of my cock pushed into her ass helped, as I think I literally lubricated myself on the way in. I could never time it like that on purpose, I bet.
We fucked one more time last night, but I didn’t cum, nor did I care. Venus managed to break the record for most orgasms a partner’s gotten out of me in 24 hours (four), and I had had lots of sex and cum in her ass twice.
I did get one more orgasm with her this morning, but on her back. I just couldn’t move fast enough from the edge I found in her pussy to her mouth to have her swallow it, so I settled for cumming on her.
I eventually left for work and hours later when I finally visited the restroom I found the evidence that we literally fucked my cock raw this weekend. So while we managed to even out my average for having skipped so many orgasms last week, I’m going to have to pay for it in healing time this week. My poor cock looks very badly abused. And I don’t regret it in the least.