I can’t believe I have agreed to do this. It’s been too long since I’ve been with a woman and I’m tired of masturbating alone. Having never done anything with a guy before, it helps knowing that you’re only doing this because your girlfriend travels a lot with her job. This means we’re in the same boat. We like women, we just can’t be with one right now.
We are going to watch porn and masturbate, nothing else. It’s weird I know, but perhaps just being around someone will help. Please don’t make this weird, not any weirder than it already is.
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I came over to your place and after a brief introduction you showed me your porn stash and asked me to pick something out. Putting porn on so quickly wasn’t rushing things, we both knew why I came over so there was no reason to act like we were old friend just hanging out, If anything, putting the porn on reduced the stress of our first meeting because I no longer had to wonder how we’d transition to the “other” activities.
We both undressed as the porn played. We were sitting next to each other on the bed as we stroked our own cocks. We didn’t talk as we stroked, but that time allowed for my “arousal brain” to kick in.
You saw how hard I’d become, so you took a chance, hoping my “need” had reached a high enough threshold I wouldn’t object. You stretched out your free hand and began stroking my cock as you continued to stroke yours.
Even though you didn’t stroke my cock the way I liked best, I didn’t stop you, and the very fact I wasn’t the one stroking it, was a turn on.
After a few moments, my incessant need to keep things “fair” kicked in so I reached over and placed my hand in your lap. When you saw what I was about to do, you moved your hand off of your cock so I could take over.
Your cock felt foreign in my hand but I didn’t get to contemplate that too long because soon you descended down my body so you could take me in your mouth.
Even though we hadn’t discussed you sucking my cock, I was too turned on to stop you or object.
You licked and sucked my cock, but you were careful to ensure you didn’t make me cum. You were aware that once I came, my “arousal brain” would end and my mindset might change instantly. If that happened I might want to leave or feel like I’m being pressured to stay until you finish. In either situation I might leave with a negative impression of my time at your place and you didn’t want that. You hoped I would want to come back.
Using an abundance of caution, you stopped sucking my cock before I was at risk of cumming. With your mouth no longer on me you sat next to me again and your hand returned to my throbbing cock once more
After the partial blowjob you gave me, my arousal was even higher which led my hand to find your cock too, so we could both continue our trek towards orgasmic relief. The uncomfortable truth was, your hand was no longer what I wanted.
As I thought about your mouth, I realized I hadn’t kept things “fair.” Without thinking about what I was doing I let go of your cock and replaced my hand with my mouth.
Even though I’d never even considered what it’d be like to suck another guy’s cock, I suddenly found myself doing it. The problem was, my personality doesn’t simply drive me to “keep things fair”, it also insists that I “always do my best.” So, even though blowing you hadn’t been the plan when I walked through your door, I suddenly felt compelled to do a good job. If I was going to suck your cock, I had to do it in a way I believed would make you cum.
I knew I must be doing something right because I could hear how you responded to what I was doing, and that motivated me to keep going. Before long I heard you say the three words of orgasmic warning…”I’m gonna cum”
Upon hearing those words, I pulled away just before you came on your chest and stomach.
Having seen you cum, my desire to do the same grew stronger. I moved next to you in the bed as I started stroking my own cock. I needed relief, even if I had to do it myself. However, you were a good host and after only a few strokes by my hand your mouth approached my cock again. When I saw your intent, I happily removed my hand, giving you a forbidden access to my body I never knew I could desire.
I didn’t want to hold back any longer nor did I want you dragging this out in an effort to build my need further. I came over thinking we’d do nothing more than stroke our own cocks while sitting next to each other, but now that we had done more, I wanted more. Fortunately, you wanted me to cum almost as much as I needed to, so you weren’t waiting long before I said those same 3 pre-orgasmic words to you.
After I came all over my chest, my arousal brain left abruptly. We exchanged a few polite words as we cleaned up, but then I drove home. — It wasn’t anything personal or something you did, it was that my mindset changed when I came and hanging out with you at that point would have felt weird.
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I wait a little bit before I see you again. I needed time to process all that had happened and to determine if I could do it again. Eventually, my own arousal and lack of a sexual outlet compelled me to make a second trip to your place.
The next time I came over, the scenario played out in virtually the same way it did the first time. That repetition was good because that gave our activities a “familiar” feeling. Since I knew what to expect I relaxed more and was able to enjoy the situation in a slightly different way the second time.
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The third trip to your place was the same, yet again. We sit on your bed, getting ourselves hard before our hands swap places. Being my third visit, I found myself waiting for the moment you would go down on me. I both enjoy, and hate, the fact you stop halfway through my blowjob, but I no longer hesitate taking my turn sucking your cock. I find it refreshing that I can make you cum so easily and consistently. Even better than that is the knowledge that once you cum, your mouth will give me the same attention, causing me to explode as well.
These past few trips have been foundational because they’ve taken me from being unsure of the unexpected, to having me accept, and look forward, to the way we both cum.
Despite this change in thought process, I’m not attracted to you, or other guys. If given the opportunity, I’d be with a woman and never see you again. You’re simply a way for me to experience sexual relief and nothing more; however, knowing that your hand and mouth are the tools which will give me pleasure is no longer a reason for me to stay home, unfulfilled.
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The fourth time I visited your place you deviated from our familiar pattern, as you offered a test to see how comfortable I had become.
As I walked into your place I already knew that we would stroke and suck each other’s cock. Honestly, I wished I was licking a pussy instead, but the fact your cock would be in my mouth is no longer the mental hurdle it once was. In fact, knowing that you would suck my cock was the very reason why I’d driven to your place today. I may not be able to openly admit it, but deep down I know that in exchange for you sucking my cock, I’d gladly suck yours.
When I came into your place we went back to your bedroom as always. However, instead of going through the ritual of picking out porn and then undressing, you undid your pants and then guided me to my knees and your cock.
You intentionally did not have porn playing or offer me the chance to become hard. You didn’t want me swept up in “arousal brain” because you wanted to know if we’d reached the point where we could pleasure each other, without any outside influences or it being restricted to the “heat of the moment” situations, and excuses.
While I was taken by surprise by this change, I didn’t fight it. During my last visit I barely watched the porn, although it’d helped just knowing it was on as it allowed me to tell myself everything we did had been motivated by porn-induced “arousal brain”. But now that I’d placed you in my mouth, without being touched, or even being hard, I could never again comfort myself with the thoughts, “I was just following his lead,” or, “I was too aroused to stop”
Once I’d proven that I was actually sucking your cock, and not simply going through the motions to humor you, you told me to make myself hard. Just like going to my knees, I did as instructed without a fight. I didn’t remove my mouth from your cock as I reached down to open my pants so I could start stroking my own cock.
Whether it was intentional or not, I’m afraid that my mind saw the flow of today’s events as, “I started sucking his cock and then I became aroused”. That subconscious seed is small, but over time it might grow, linking my arousal to making your cock hard. Is that something I should be worried about?
You were pleased that we had crossed this new line so you rewarded my progress by switching places with me.
Just like every time before, you didn’t let me get too close to cumming before you stopped sucking my cock. Once my mouth was on your cock for the second time that day, you softly reminded me to “keep myself hard,” so I did
I was still stroking my cock as you came in your hand, and the eruptions from your cock had barely subsided before you told me to lay down. Excited that the reason I had come over was finally here, I went to your bed. I found myself moaning as I watched my hard cock disappear between your lips.
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The next time I visited your place I found myself on my knees once, making you cum, without any porn or fanfare to spur us on.
During my entire visit you only had to tell me to “keep myself hard” once. I’ve come to understand that you expect me to be hard at all times, so any time your hand or mouth wasn’t on my cock, I stroked it.
Actually, I don’t mind this new expectation because it results in a stronger reaction and more intense feeling of pleasure, the moment your lips engulf me.
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I’ve lost count on the number of times I’ve visited your place, but today, when I said “I’m gonna cum,” you didn’t pull away. I have never asked you to swallow my load, but now that you’ve done it, I secretly hope it wasn’t a one-time thing.
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During the next visit to your place you swallowed my load once again, even though I had moved away when you came, only minutes before.
While I prepared to leave, my sense of “keeping things fair” rose up and suddenly I felt like I’d done something wrong. I mean, I had no idea you would swallow my cum the last time I saw you, but I had been fairly confident you’d keep doing it. If I had really anticipated that, why hadn’t I at least considered doing the same for you?
The guilt I felt was so bad that I asked if I could come back a few hours later. During that second visit, when I heard you announce that you were going to cum, I wrapped my arm around your waist, to ensure I wouldn’t pull away at the last second.
You didn’t seem surprised when I grabbed you like that, and part of me suspects that you had known that “returning the favor” had been the real reason I wanted to come back so soon.
As it turns out, swallowing your cum wasn’t so bad. By not having to make a last second retreat and then pump your cock across the finish line, the ending felt less awkward and more natural.
Now that I’ve finally remained in place, I can admit that swallowing your cum is both easier, and more convenient. I just wonder if the day will come that the thought of moving away no longer enters my mind. Will there ever be a day that I’m turned on by the thought of tasting you? I don’t see how either of those things could be true, but then again, I’ve done more with you than I ever believed I possible.
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A couple weeks after I started swallowing your cum, you decided to see if I was ready for more. While you were going down on me you moved lower and I felt your tongue on my ass. Just like everything new you’ve done, we hadn’t discussed doing this and you didn’t ask me if it’d be ok. You just did it, without offering me a choice, and I responded by offering no objection. .
Obviously you can’t suck my cock and lick my ass at the same time, so you told me to keep myself hard. I started stroking, but I only stroked enough to keep myself hard because I enjoy cumming down your throat.
Once more, you didn’t ask what I wanted, or how I wanted to cum. Instead, you stopped licking my ass just long enough to say, “I want you to cum while I do this”
Before that day I wouldn’t have thought having my ass licked would feel good, but it didn’t take long before I found myself enjoying it. Actually, it went further than just enjoying it. I soon discovered how easily, and hard, your tongue could make me cum as you stimulated me in this entirely new fashion.
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The next time I came over I wasn’t surprised when you began to lick my ass again, but you didn’t lick too long before your mouth returned to my cock. Initially I thought that was just the start to an alternating pattern of pleasure, as we sucked each other’s cocks, but I realized I was wrong when I felt you touch my ass.
Something about the way you touched me told me your hand wasn’t there by accident. While I might have been in denial as to what you are going to do, I wasn’t actually surprised when I felt your finger slipping into the hole you just made wet with your tongue.
Before I left your place, I had kept things fair by licking your ass too. However, the experience I’ll remember most was the sensation of cumming while my prostate was massaged for the first time.
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I knew where things were headed the moment you fingered my ass. It’d be counterproductive for me to deny it or pretend otherwise. You’d left enough clues in the past signaling your true desire.
A week ago you casually mentioned that you’d let me fuck your ass if I really wanted to, and I’d neither encouraged, nor discouraged, that thought. I can now see that remaining silent had sent a message of “we can move that direction”
The thing is, I’m happy with what we do and how we make each other cum. What I fear most about your offer is that if I ever fuck you, my sense of “fairness” will insist that I let you do the same to me.
As much as I want us to just continue sucking each other off, it’s obvious that you want more. I can see how you’re trying to prepare my ass to have something inside of it, and it’s becoming clear that will happen, even if I continue to ignore the offer of yours.
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I spent the next few days thinking about what I know you want and my willingness to let you do that. Truthfully I really don’t want you to fuck my ass, but when I ask myself “why” it boils down to nothing more than long held biases.
I know that if I tell you I don’t want you fuck me, you won’t, but I also know we can’t go backwards. I enjoyed your finger being in my ass, so why would you stop doing that? If we continue doing that one thing, in time one finger will become two. Soon after that two fingers will become a small plug and then that plug will become bigger.
Like most things in life, there will be a natural progression, and because of that, I already know that if I ask you not to fuck me, all I’m doing is delaying our timeline, not stopping it. If I’m really against you fucking me I can never visit your place again. Never seeing you again is the way I can really be sure your cock doesn’t end up in my ass.
I’m still not attracted to you, and we’ve never kissed because I consider that to be a sign of affection and romance. I don’t have those feelings for you, or any guy. Going to your place is only about feeling good, and I do enjoy the way I cum when I’m at your place. Plus, it’s an ego boost knowing that someone invites me over because they want me to make them cum.
A younger version of me would be surprised to hear that I don’t want to stop giving, and receiving, head from a guy. That uncomfortable truth is making me conflicted over how to handle this situation.
I wish this decision wasn’t coming down to being willing to cross the “sex” line, but it has. I want to believe there are lines I won’t cross, but since meeting you I’ve learned that I’m so addicted to pleasure, there’s little I won’t do to keep getting my fix.
While writing this I feel like I’ve made a decision, but I want to test my resolve to be sure. Once I put this notebook down I’m going to masturbate to gay porn, while I finger my own ass.
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By the time I saw you today I had already started using a small plug in my ass each time I masturbated. When you placed a finger in my ass during my blowjob, you noticed I wasn’t as tight as I had been last time. Sensing the difference you must have realized I had been placing things inside me when alone.
You failed to see the difference between me “preparing for the inevitable” versus “wanting to be fucked”. You must have believed I wanted more so you pushed a second finger into my ass. A minute later you prompted me to go to my knees.
As I went to my knees I told myself you’d move in front of me, so I could suck your cock, but you didn’t. You remained behind me and rested a hand on my hip. Things were happening too quickly and things were going too far. For the first time since coming to your place I almost told you to stop. I opened my mouth to utter that four-letter word and then I reminded myself that this was inevitable. After all, hadn’t I purchased a butt-plug? Hadn’t I put it inside of me so I could start preparing for your cock? Whether it was today, next week or next month, this was going to happen, so what was the point in delaying if you wanted it now?
Once you touched my hips you didn’t do anything else. I’d like to believe you were giving me a chance to object, and when I remained silent, you pointed your cock at my hole and leaned forward. As your cock entered me I bit my lip, willing myself to relax.
Your cock was bigger than the plug I had been using and I had just managed to get used to the discomfort and pain right before you pulled out.
The sensation of being fucked was more different than I could have imagined and the pain of my first time was so distracting that I couldn’t cum.
There was something about my ass being sore and feeling like I needed to go to the bathroom, that didn’t put me in the mood to keep going. Once you deposited your load on my back I cleaned up, got dressed, respectfully excused myself and returned home, with my balls still full.
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My biggest fear, and greatest taboo, has officially happened. I can’t go back or undo the fact I let you fuck me. I either have to stop seeing you or let you continue doing it. Those are my only choices, and I’m not writing this because I can’t decide between them. I’m writing this to say that the personality trait which drives me to “do my best,” dictates that I practice, so I can get better.
Yes, the plug I purchased had been a good start, but you showed me that “fucking” was very different than placing a small plug in me and leaving it there. Unsure of what else to do, I went back to the adult store and bought a dildo and harness.
Why did I buy both? I wanted the ability to attach the dildo to pillows, chairs or even the headboard. Maybe this isn’t a good idea, but I feel like I need to recreate positions I might be fucked in so I’m ready for whatever you might try. For once, I’m glad that your girlfriend is back in town as that gives me time. I think I’m going to need time for this.
Finally, I want to make one thing clear. Very clear. I didn’t purchase the dildo and I’m not practicing like this because I want to be fucked. Being fucked was neither amazing nor pleasurable. However, I feel like learning to enjoy being fucked will be easier than trying to ensure it never happens again.
What does that mean? Simple. In order to keep seeing you, I need to welcome your cock in my ass, just as easily as I do in my mouth.
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It’s been nearly three weeks since the last time I saw you, and the “real-size” dildo no longer hurts. More importantly, cumming with the dildo inside of me has become much easier.
Over the last 3-weeks the only conversation we had about what happened occurred when I replied, “It’s fine, don’t worry about it.” Given my quick termination of that topic, and the fact I hurriedly left, without cumming, I knew that you might be reluctant to fuck me again so soon.
The topic of being fucked still feels taboo to me so I haven’t known how to tell you that I’d come to terms with it. And while I could wait for things to shift that way again naturally, I don’t want things to be awkward between us until then. Unsure of what else to do, I took a page from your book and decided to just act.
As soon as we reached your bedroom I went to my knees in front of you. Once my mouth had made you hard I asked you to lay down on the bed. You probably expected me to continue my blowjob as you reclined, but instead I straddled your body so I could lower myself onto your cock.
Your cock was warm and felt very different from the dildo I’d practiced with, but the differences were mostly good. Unlike the last time your cock pierced my depths, this time I was able to enjoy myself. I still remember the surprise on your face when I came on your chest, just moments after I told you to just cum in my ass.
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I’ve been over to your place nearly a dozen times since the first time I rode your cock, and since then you’ve fucked me almost every time I’ve seen you, and yet I’ve never fucked you. While that may seem “unfair” because only one of us is being fucked, I see it as being practical
I like the fact that you can cum first and you still want to make me to cum after that. I don’t know if I’d be just as motivated for your orgasm if we switched that order around. My fear is that if I cum while fucking you, and you don’t cum too, then I might have to mentally force myself to suck you off. And what if you want to fuck me after I came inside of you? I can’t see how being fucked, once I’m no longer aroused, would be enjoyable. Would I start to hate being fucked or would I start resenting your need to cum?
The only way I see our arrangement continuing to work is by having you cum first, or by having both of us cum at the same time. The inescapable fact is that, I know I’ll cum when your cock is in my ass, so even though it may not be “fair” that I’m the only one being fucked, I’m not willing to risk upsetting the balance by gambling on your ability to cum from my cock inside of you.
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I just got home from your place, and for the first time, we both came twice in a single visit.
It started with us in the 69-position, but once we both came you asked if I wanted to stay and watch a movie. Just after the action flick reached its climax I felt yours running out of my ass and down my leg.
As much as I’m ok with our transition to actual sex, I still enjoy your mouth the most. Why? It’s because, when you’re sucking my cock I know that you’re focused only on my pleasure; whereas, when you’re in my ass I know you’re primarily focusing on yourself.
Don’t get me wrong, the orgasms while I’m being fucked feel good, but I like being able to cum while your mouth does all the work, instead of my hands. Maybe on my next visit I’ll ask you to let me finish down your throat, once I’ve let you empty yourself in me.
Honestly, just thinking about that has started to make me hard again. Too bad your girlfriend comes home tonight, I guess I’ll have to recreate that scene on my own using one of my dildos and a fleshlight.
It’s funny, I can still remember being nervous when I bought my first dildo, but now it feels weird to masturbate without one.
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I can’t believe how long it’s been since that first visit to your place. I’ve been dating a wonderful woman for almost 9-months now and we have a very active sex life. She knows about you and hasn’t condemned me for anything we ever did.
My birthday is next Saturday but she’ll be out of town due to a bachelorette party. She says she wants to make this first birthday together memorable, and since she can’t be here for it, she asked me for your number.
When I asked her what the two of you talked about, she replied, “About my expectations”.
Of course I asked her “what do you expect?” to which she gladly told me, “By the time I get home Sunday night I expect you to be so drained that you’re unable to get hard, no matter what I do”.
Here’s the thing about her. She means it.
On Sunday night I suspect she’ll pull out all the stops in an effort to make me hard. I don’t think she’ll feel like I really appreciated her gift, if I’m able to get a boner. This means you’re gonna have to completely wear my cock out. Are you going to be ok with that after all these months of not seeing each other?
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My girlfriend leaves town for her bachelorette trip tomorrow. I had expected a wild night of sex with her since she’d miss my actual birthday, but she surprised me yet again.
Apparently she asked you if I could use your “pussy” this weekend, since hers would be 300-miles away. Not only did you tell her “yes” but you said that you’d happily give me your virginity, since you’d taken mine.
When she found out that I’d be your first she decided to start my time with you tonight, instead of tomorrow after she left.
When she told me you were coming over tonight, she made it clear that she didn’t invite you over for a 3-some. While I wasn’t surprised to hear that she wanted to watch me fuck you for the first time, I was shocked to hear her admit that she also wants to see me make you cum, while my balls are empty.
I told her that I never cum first, but she replied, “I know, but you will tonight.” I started to explain why you had to cum before I did, but she responded by saying, “He’ll be here in 45-minutes. While I pack for my trip, why don’t you come to terms with the fact that you can cum first and it won’t matter.”
I’ve been sitting here, thinking about what she said as I wait for you to arrive. One thing I know for sure is that I’m not attracted to guys. I don’t want to kiss you, make-out with you or be in a romantic relationship with any guy. But, I can’t ignore the fact that she’s right. I do like the things we’ve done and it’s time I stopped pretending like I have to be in a pre-orgasmic state before I can take your cock or swallow your cum.
I shouldn’t have to say it, but I love her. I love her terribly, but she’s also making me think about the fact there are other things I enjoy too. There are things which she simply can’t provide, and I’m not sure how to tell her that.
Actually, I guess she knows that. Maybe that’s the reason she reached out to you. Maybe this is her way of saying she loves me enough to let me indulge in those desires. Or maybe this whole birthday-weekend cum-fest is more about her, and not me.
Could that be true? Have I been misreading her intentions this whole time?
I’ve been thinking that she’s trying to get me to finally accept that I like being with a guy, but let’s be honest, that isn’t a giant leap anymore. No, the real purpose of this weekend could be for her to discover her reaction.
While she’s well aware of what we’ve done, the difference between hearing stories and seeing it first hand is huge. Maybe she’s wondering if she’ll get mad if I’m unable to get hard because someone else made me cum first. What about jealousy and repulsion? Could she be worried that negative feelings might creep in or prevent her from opening her legs to me if she also knows the taste of cum is still in my mouth?
I don’t know why, but those fears make sense. I think she may be testing herself to see if she can handle what we’ve done and to find out if she is capable of sharing me with someone else, on a purely physical level.
If that’s the case, then I owe it to her to not hold back. She needs to see you cum in my ass and down my throat. The moment you leave I need to devour her pussy as if I’m a starving man and she is the only food for miles. In the middle of the night I need her to wake up, as my cock is sliding into her. as if I’m so desperate for her body that I can’t wait a second longer.
By the time she leaves town tomorrow I want her to know that my “other” desires won’t damage our relationship or replace my need for her pussy. I think it’s important that she understands that I can enjoy, and want, both.
Did I just say what I think I did?
I did.
I think that’s the first time I’ve ever said that.
Doing things with you was always something I did because I had no other sexual option. But, I have another option now. I have an amazing girlfriend and we have mind-blowing sex, yet I didn’t even consider turning down the offer to spend the weekend with you. Why am I just now realizing that?
I want her pussy. I love her pussy. I’m virtually addicted to the way she tastes, but I want your cock too. I can’t believe I’m saying this but, I want your cock, even though I can have her pussy.
Now that I’ve admitted that, I know she’s right. I know that after I cum in your ass tonight I will immediately go to all 4s for you. Soon after I will stroke my cock as I suck yours, not stopping until your second load is my throat. I’d want to do that, even if it wasn’t the show she was expecting to see.
I want this. I want cock, and after this weekend, I’m not going to want to give it up. I hope she’s ok with that.