My second time with a man

SergioDecember 2, 202316 min read3.3K views

Continuation of the story My First Time with a Man

After the incident described in the previous story, a series of events occurred that I want to share with you, dear reader.

After Max left, I couldn't think of anything except what had happened to me. My thoughts were jumbled and shifted like a kaleidoscope. I felt I couldn't wait for my wife to return and decided to relieve the tension myself, but I had barely run my hand

over the shaft a couple of times before I came. However, even after the release, I didn't calm down and realized I wanted to write a story about it, which I proceeded to do. With trembling hands, I drafted the story, sent it to the website, and while waiting for my wife, I simply sat on the sofa, finished the remaining cognac, and listened to my feelings and thoughts.

We had long ago agreed that we have no secret lovers, male or female. This is part of our agreement, and without it, we wouldn't have lasted so long together. It's probably strange to talk about fidelity in such a relationship format, but precisely the fact that I always know where my Olya is and with whom, and that she will definitely return to me, allowed me to be confident that she is faithful to me. I'm sure she felt and feels something similar.

As I mentioned, my wife herself sometimes fooled around with girls. But no one would call her a lesbian. Digging through my memories, I realized she had only met one-on-one with girls a couple of times at most. 90% of her lesbian experience was in group orgies, where she was simply aroused, and the girls served merely as seasoning to the main course. I tried to apply my opinion about my wife's escapades to myself, to my own feelings, and couldn't understand what would happen to me. Now that I had crossed a certain line, thoughts of sex with a man no longer seemed so attractive to me, though I definitely wanted a repeat. For myself, I understood that this would be a special spice in sex for me, and I didn't plan to do it particularly often. I just didn't understand how my wife would react.

Olya returned from work as always, late. While I was on vacation, her lover gave her a ride from work, and every day he somehow fucked her on the way home. This time too, as Olya told me, they pulled over on a quiet street where she blew him, and he came in her mouth without even fucking her. However, she didn't hold a grudge against him, as she had gotten a good fucking from her boss and knew that I was waiting for her at home and she wouldn't be left without a well-deserved orgasm.

"And get this, he didn't come in my ass like usual, but pulled out and came on my back. He's decent, of course, helped me wipe off with wet wipes, but some got on my stockings, and I didn't even notice. Only when I was getting ready to leave work and change shoes, I touched my thigh and there was such a giveaway. Probably many people guess I'm fucking him, it's nothing new here, but still, walking around all day with cum on your stockings is kind of embarrassing," Olya recounted quite matter-of-factly.

"So, all day?" I kept the conversation going.

"Well, yes. He called me right after the morning briefing. It hadn't happened in a while, he pounced like a beast, bent me over the desk, fucked me, and left on business. I didn't even have time to ask what happened. Probably someone fucked him over at the briefing, so he was taking it out on me," Olya said with a chuckle. I also smirked.

"Well, at least he fucked me hard, the way only he can. And you, did you see Max?" she asked the question I had been fearing and waiting for with a tremor in my soul.

"What do you mean, 'at first'?" Olya was stung by the idea that he might not have wanted her. "Did you fuck someone with him? Did you invite Lenka?"

With these words and a playful smile on her face, Olya sat on my lap. With one arm, she hugged me, and with the other, she began stroking my cock through my shorts, awaiting details.

"Well, he probably wouldn't have refused to fuck such a doll, but he got something else," I added intrigue. My darling's eyes were literally burning.

"Come on, tell me, I want to know everything in the smallest details," it was noticeable that Olya was on edge, and she spoke playfully and coquettishly. Under these urgings, she mounted me and inserted my cock into her dripping pussy. Moving more and more actively on my cock, she continued to urge me to tell her everything. And I told it like it was.

"I got him. We were reminiscing about how we double-teamed you, and I got so turned on that I sucked him off." Olya stopped for a couple of seconds, looking into my eyes. A smile slowly spread across her face.

"Ah, yes!" Olya finally exclaimed, pressed against me, and began a natural ride, whispering in my ear, "That's so awesome, maybe we were sucking at the same time. I so want to see that, no, better to participate, to suck together with you. And even better..." At that moment, Olya was shaken by an orgasm. She had little control over herself, but holding her by the ass, I quickly moved with her to the bed and continued to fuck her mercilessly until she was completely exhausted. Without coming myself, I collapsed next to her.

All evening we discussed what had happened to me and how long these desires had been tormenting me. We resumed our coupling more than once, but I only came when Olya, in the frenzy of another orgasm, shouted: "Yes, bitch, fuck me, my little faggot." By the way, Olya very rarely uses swear words, and it always means she's losing control of herself. Realizing this led to another orgasm for me as well.

We talked until late at night. Olya was, as always, very attentive and showed complete involvement. She convinced me that her attitude towards me hadn't fundamentally changed; on the contrary, she was glad I could overcome this barrier on the path to pleasure. Of course, she immediately suggested arranging a joint orgy in any format. I promised to think about it but immediately said that if I did decide to offer my ass to someone, it would be someone like Max, who couldn't somehow disgrace me. After all, such desires are, to put it mildly, not encouraged in our society. We agreed on that. I noticed with surprise that I was insanely aroused when Olya called me a fag or faggot. She does it in a completely special way, not like men say it, but with a kind of affection.

Our life continued to flow as before, except that in sex with Olya, there was even more depravity. She ordered a strap-on and fucked me with it twice, but it's not the same at all. When a rather fragile young woman is panting behind you, it's still not the same as when a strong, athletic man is fucking you. I decided it wasn't for me, and we decided to use the strap-on on Lena sometime when the opportunity arose, to fuck her together.

But then, two months later, Max got in touch, this time writing directly to me. He wrote that his extended work shift was over, he was heading back, would be passing through our town again with a layover, and that he wanted to repeat with us, but this time he wanted to not be constrained by train schedules but to go all out. My wife and I quickly conferred, and since we both desired it, we quickly agreed.

Max booked tickets so that he arrived at two in the morning and left only near dawn, all on a Saturday, so we had plenty of time for an orgy.

As soon as we returned from work, preparations began. My wife helped me shave clean everything that needed to be shaved. It was a very emotional moment when my wife shaved my ass so that I could be fucked in that very ass. After all the cleansing procedures, she played with my ass and shared one of her anal plugs with me. Once, Olya's boss gave her a set of anal plugs with stones of different colors; she gave me the one with the green stone and inserted the red one for herself. We really wanted each other but decided to wait for our guest. The wait was terribly agonizing. We made the bed with fresh linens, tidied up the house, prepared snacks, and did all of this naked with plugs in our asses – it was insanely arousing.

When the doorbell finally rang, Olya, still naked, rushed to the door. I would have liked to see Max's face when the door opened and an absolutely naked, beautiful young woman appeared before him, but it wasn't meant to be. While I took his bag of things to the room, Olya showed Max to the bathroom. We turned on the TV and started a video featuring a large-scale bisexual orgy. My wife and I decided that such accompaniment would help spur our imagination. It was the first time I sat with a plug in my ass, and every movement sent waves of arousal through me.

By the time Max came out of the bathroom, Olya and I were sitting on the sofa, and she was stroking my already quite tense cock. We were sitting naked, and Max only had a towel as a loincloth. As usual, we had a drink to celebrate the long-awaited meeting, exchanged a few words about his business trip, but the tension was palpable in the air; we all understood why we were here and all desperately wanted it.

Finally, after downing a shot, Max stood up and approached me. He dropped the towel, and his amazing cock appeared right in front of my face. It was already hard and trembling as if with a heartbeat. I didn't hesitate for a moment; licking my lips, I fell upon that cock. First, I ran my tongue along the shaft from the base to the frenulum, then started licking the head (I'll add that, in my subjective opinion, doing this sitting on a sofa is much more convenient than kneeling). At the same time, Max and Olya let out practically simultaneous, very similar moans from a distance. I glanced sideways at Olya – she was sitting with her mouth open and eyes wide, watching intently and apparently having a hard time believing the reality of what was happening. After I had slobbered all over Max's cock, I moved on to thrusting motions, holding his cock with one hand and stroking his thigh and stomach with the other. But then Olya snapped out of her stupor and moved right up close to me. We began sucking alternately, while caressing each other, and even licking that beautiful cock together. It was very exciting and still resonates warmly somewhere deep inside. Of course, I had seen Olya suck other men before, but doing it together with her was something special. And then, finally, Max turned us towards the back of the sofa so that we were standing side by side, leaning our elbows on it. He entered Olya's ass first; at that time, I was stroking and squeezing her breasts, which were swaying under Max's thrusts. He fucked her just a little bit, then pulled my plug out of me. I glanced back as much as my position allowed and saw that he hadn't just taken the plug out of me but had placed it in Olya's ass, filling mine with his cock. He entered very easily; it remains a mystery to me how that works, because the base of the plug is quite thin and shouldn't stretch the sphincter much, but the sensations are radically different, and I definitely decided that if you want pure pleasure from anal sex, you need to prepare not only in terms of cleaning but also definitely wear a plug for at least ten minutes, and then you'll be guaranteed magical sensations.

Olya stroked my back and kissed me passionately while Max held me by the waist with his strong hands and drove his piston into me.

He switched our asses several times like that, and when he wanted to switch to Olya's again, she said she wanted us to take her together, like in the good old days. With the plug in my ass, I sat on the sofa; she mounted my rock-hard cock, and Max positioned himself at her ass. We fucked her like that for a while, but keeping the same rhythm is not easy at all, as it depends on the woman, who in such a situation has poor control over her body. In the end, I slid down and lay on the sofa, Olya on top of me, and Max above us. Hugging and securing my darling, I could control the rhythm myself, and Max and I were able to drive our cocks into her simultaneously without missing a beat, quickly bringing her to orgasm. Olya went from moans to cries of pleasure, asking for more and more, and we still didn't stop. I felt her go limp on me and become just a doll on our cocks, but we continued to fuck her. Finally, Max couldn't hold back and, in his characteristic manner, began calling Olya a bitch and a whore while pumping his sperm into her ass. This time, this male wasn't pounding me into the sofa from behind but was towering over me. I liked his appearance and the words he used for my beloved, and I wanted next time to also be facing him when he came in me.

Olya lay on the sofa, barely breathing, and Max and I, having caught our breath a bit, decided to have another shot.

Barely having a chaser, Max abruptly approached me, hugged me with both arms, and kissed me. At first, I was stunned, but he continued to push his tongue into my mouth. Recovering from the stupor, I returned his kiss and began stroking his back. Then he bent me over the coffee table, took the plug out of me, and began fucking my ass like a man possessed again. It seemed to me that this time he had even more energy than the very first time. He grabbed me by the elbows and lifted me. It turned out that I was now leaning on nothing, and Max was not only driving his cock into me but also pulling me onto him. At the same time, partly to not fall, partly in sweet pleasure, I myself pushed back, impaling myself on the piston of my stud. Nevertheless, holding this position wasn't easy, and when Max got a little tired and eased the pressure, I suggested he lie on the carpet, and I mounted him, sitting facing him and bracing my hands on his chest. So I rode him, if you can call it that, more like wiggling. Maxim stroked my thighs and caressed my cock with his hand, as much as my movements allowed.

Then I noticed that Olya had already recovered from her orgasm and was watching us with interest. When our eyes met, she got up from the sofa and approached me with a charming smile.

"Oh, you, my clumsy little faggot, let me teach you how to give a man pleasure," Olya said, gently pulling me back. I leaned back, bracing my hands behind me. She also showed me how to position my legs and at what angle to start riding. Her advice was very timely; pleasure spread in waves through my body, and my rock-hard cock slapped against my stomach. While Olya kissed me and pushed her tongue deep into my mouth, Max's cock penetrated deep into my ass. At some point, I realized I was slamming down onto him all the way, and it was insanely exciting. Apparently, Max liked it very much too, and he growled, "Yes, bitch, I'm gonna come now." I abruptly changed position, returning to him and rolling over my side, pulling my stud with me, ending up under him. Maxim, grabbing my wrists and holding me down, began to growl furiously and drive his cock into me, while I lay submissively under him with my legs up, enjoying it, catching the changes in his facial expressions and literally feeling his pleasure. Right before his release, our eyes met.

"What an amazing ass you have," Max growled this, then leaned down and pressed his lips to mine. This time, I returned his kiss without the slightest hesitation, and he rewarded me by filling my hole with his seed. Through the kiss, I moaned with pleasure; the tenderness of the kiss multiplied the pleasure from the roughness of what he was doing with his cock.

After emptying into me, Max kissed me long and tenderly. When his cock finally went soft and he pulled out of me, I looked around and realized Olya was in the bathroom. Max noticed this too.

"You still haven't come," he said, running his hand over my erect cock. Max turned to me, leaning on one elbow, and with his other hand began to jerk my cock and kiss me on the lips. After everything that had happened, it took me less than a minute to come in his hand.

"You're an amazing fag. Mind if I call you that?" Max asked.

"Asks the man who just fucked me and is holding my cock in his hand," we both smirked. After that, I pulled his head towards me myself and kissed him as tenderly as I could. He responded with enthusiasm.

"Look at the lovebirds," Olya's playful little voice came from behind Max.

Maxim moved away from me and lay on his back again, and Olya lay on her side next to him.

"Ooh, and it

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