It wasn't the first time, but it was the best one yet.
Between shyness and abandon.
It was late Saturday night. One of those days when you don't have a plan, but you're looking for something to do. Lying on the sofa, thirsty like a hunter, but with no plan. The TV on in the background, phone in hand, sending messages in case anyone around wants to grab a drink, we'll see.
While in the shower, a WhatsApp notification pops up. I barely dry my hands to see who replied. Zara. (Hey my little mulatto, how's it going?) A smile spreads across my face, and anticipation... That's it! Anticipation!
"Hey my skinny girl. What are you doing, shall we grab a drink?"
Her reply: "We're at El Encuentro (a local bar), we just got here."
Zara is the kind of friend you haven't known for very long, but with whom you quickly form a bond that's hard to explain. Slim, hence the "skinny girl." Short red hair, small breasts, a round, firm ass like concrete. He lives with his girlfriend, whom he hasn't been with for very long, but for Valeria's first time with a girl, things aren't going badly at all. I suppose either we men have disappointed her a lot, or it was something she'd been repressing inside.
Before he was with his girlfriend, he used to visit me fairly often. We'd have long conversations accompanied by plenty of beers, weed smoke, and the occasional snort.
I'm a discreet person in general, especially when it comes to my sex life. I'm not one of those men who brag about their conquests; quite the opposite, I prefer that no one finds out. I've told her about adventures I've had, but never mentioning names or giving any clues about who they were with. I have to admit that I fall into the promiscuous category, and quite a bit. I wouldn't say I'm a sex addict, but I am a bit of a nymphomaniac. It's something I've loved since I was very young, considering that I was twelve when I lost my virginity, with two older girls. I won't go into details now so as not to make the story too long.
In one of our conversations, she told me about her encounters with other girls, including details and answers to all my questions about sex between women. Then a pop-up window on the computer screen caught our attention. She pointed at it and said, "You got a message." A girl's picture was clearly visible. I acted like it was nothing, but she insisted on seeing what it said. So, while clicking on it, I explained that it was from a dating site, and that before she arrived, I had been talking to this girl about meeting up. This only increased her curiosity. She asked to see the profile pictures, and when I showed her the first one, she exclaimed, "She's a trans woman! I think..." Of course, she wasn't wrong. And I confirmed it. Up until that moment, even with how sexual our conversations were, I hadn't told her about this.
"She's very pretty," she commented. Followed by, "I didn't know you were into them, I never even imagined it."
"To put it bluntly," I said. The truth is, they turn me on quite a lot. What's more, I'm going to tell you something I've only shared with Roo. (Roo is a mutual friend.) I'm pretty open-minded; I don't label myself with any of the trendy definitions. I simply let myself go in search of pleasure.
"Okay. So you're bisexual," she said and laughed, before continuing to bombard me with questions.
"And what do you like to do with them? How do you find them? How many have you been with? Do you fuck them or do they fuck you? Have you ever given them a blowjob? Have you also been with men?" And a few more questions.
Watching me intently as I began to answer. The kind of attention someone can't hide their interest gives. I told him how my curiosity to try different things had started, that my preference was for women, that men didn't really appeal to me, but I had had more than one experience with one. That transsexuals did attract me quite a bit. Until he interrupted, repeating a couple of the previous questions.
"Do you fuck them?"
"Well," I stammered. "Most of the time we both fucked each other, there were a few times when only she fucked me."
"Ah," he said, smiling. "Your ass has been fucked." And he burst out laughing. He added that one of his favorite porn genres was gay, that he loved watching two men fucking.
We continued talking about related topics almost all night, we put on some porn videos, one of which I showed him was of a girl with a harness fucking her boyfriend. Before the video ended, he suggested I buy one to try it. Of course I accepted….
Let's return to that almost Saturday night where this story begins.
It was approximately 9:30 when I arrived at the bar where he was with his girlfriend. (The Encounter) A place without much glamour, the typical kind where a huge variety of people gather. A short bar, low lighting, moderately loud music, one side almost entirely occupied by slot machines, a waitress with large breasts and a plunging neckline. A small terrace at the entrance with two high tables and stools. One of those bars where you can buy almost anything.
Zara was at one of the tables on the terrace talking to a guy. As soon as she saw me, she rushed towards me, giving me a tight hug and three quick kisses on the lips because that's how she and I always greet each other. She introduced me to her friend, a brief handshake, names exchanged, accompanied by the typical "Nice to meet you." After the brief introduction, I was about to go to the bar to order a beer, but just then his girlfriend arrived with three in her hand. Since Zara's was almost full, they gave me one.
The night started to liven up, in a way I hadn't expected. At that point, when several beers facilitate laughter, jokes were made without shame, and innuendos were exchanged that needed to be deciphered to avoid misinterpretation. Zara asked me to join her for a smoke. I followed her to the threshold of the terrace entrance, we each lit a cigarette, and after a couple of puffs, she started talking. "My love," was the first thing she said. Followed by, "Let me tell you something, this friend of mine is more than horny for you. He keeps asking me what you're up to, saying that if you dumped him, he'd devour you." She couldn't contain her laughter… I suppose she immediately noticed the expression on my face and, without giving me time to say a word, added, "I didn't say anything to him, I just told him to tell you, that I'm sure you wouldn't mind!" Then, in a tone somewhere between question and statement, she continued, "Come on, tell me the truth, I know you. Look at him." That's great, you're not going to deny that you didn't fuck him.
"You're a bitch." That was the first thing out of my mouth. But honestly, even though it wasn't my plan, it's not bad at all.
NOTE: To make it easier to visualize. A guy around twenty-nine years old at most, according to my calculations at the time, maybe younger. Slim, very black hair, with features that could be described as delicate, brown eyes, tight jeans. And for me, a dose of surprise because of what she was telling me. He didn't look that old.
We continued talking about it for a few more minutes, giving her my approval so that if she wanted to, she could go for it.
We went back inside to the terrace; his girlfriend and the guy were chatting at the table. Zara discreetly took a small bag out of her pocket. "Do you want to have one?" We all answered yes. "Okay…" she said. "Come on, Vale and I will go to the bathroom first, and then you two. It won't take long; when I get back, I'll give the bag to… Let's call him Jon… Here. Now you go."
He looked at me, and I nodded. He walked towards the bathroom, followed by me. We went in, and I locked the door. He went straight to the toilet seat to prepare some of those sniffing bags, but I grabbed his arm and interrupted him. When he turned around, facing me, just inches from my face, I said,
"The skinny girl already told me. What do you want?"
Without answering, he moved closer and, without hesitating, lightly ran his tongue along my lower lip. I responded by pulling him closer, and we shared a brief kiss.
"Mmm. What a delicious mouth," he said softly. Then, "What else can you do with it?" He laughed.
"I smiled too before answering. "Well, a few other things."
We sniffed the small bag and left the bathroom, heading to the table. We each grabbed our drinks and joined the conversation. I felt the weight of the skinny girl's gaze, and when our eyes met she just gave a mischievous smile.
As it got later, a few acquaintances joined the table. They'd stay for a while, then move to another table inside; one of their friends stayed longer. Another round of beers, bad jokes, stories about things that happen in the neighborhood. And then the skinny girl with the bag made the same offer again. First, the three of them went to the bathroom, emerging after a considerable time, laughing uproariously as they returned to the table. I handed her the small bag to me and gestured to Jon to follow me. He nodded and walked behind me. The bathrooms in the bar are quite small; there are two for women and two for men. We went into the first one, which was the only one free. Jon quickly locked the door, and before I could say anything, he pounced. He grabbed me by the waist, shoving his tongue into my mouth. With surprising dexterity, he unbuttoned my pants, reached inside, and pulled out my semi-erect penis, massaging it a couple of times. He sat on the toilet, pulling me along, and put it in his mouth. He gave it a few hurried licks, looked up, and put it back in. I had to hold back a moan of pleasure. And then... (KNOCK KNOCK). Someone knocked on the door.
I'm not sure how long it lasted, but it felt like a long time. He pulled up my pants, buttoning them quickly, and we left the bathroom. We went back to the table, beer in hand again, joining the conversation. By then, I was hotter than a barbecue grill, ready to let the night take its course.
I moved around the table until I was next to the skinny girl, discreetly passing her the small bag while patting her on the back…
“You took a long time,” she whispered.
“Let’s have a smoke,” I suggested.
She came out behind me, we lit our cigarettes, a little smoke, followed by a light touch of her shoulder against mine. She repeated, “You took a long time in the bathroom,” and let out a laugh… “What? Tell me, hahaha.”
“There’s not much to tell,” I replied, laughing too. “Only that your friend had his dick in his mouth.”
She let out another laugh. “See! I knew it!” “And how was it?” she asked.
“Not bad, really, we’ll see what happens, there’s still a lot of night left.”
We went back to the others at the table. The night continued its inevitable course. Around three in the morning, more or less, with the weight of countless beers and something else. The skinny girl suggested buying some more beers and going to her place. Jon refused, insisting we go to his. I should clarify that they all live a short distance from the bar.
The four of us went to Jon's place. A small, two-bedroom apartment, but very cozy. Someone put on some music, and little by little, between dancing, things got livelier. Zara and her girlfriend were getting increasingly turned on and couldn't stop kissing and touching each other. Jon discreetly turned on the TV and put on porn, which heated things up even more. We were talking, I don't remember about what. When Zara's girlfriend went to the bathroom, she came over to us. She kissed me, including tongue in the mouth, and then him. She smiled, pulled us both closer, we laughed, and shared a quick kiss, to which she reacted by saying, "Just that? Come on, a real one." We kissed again, and this time it was a kiss that had everything.
There was a moment when I went to the kitchen to get a beer, and before I knew it, Jon was behind me. He pressed himself against my back, asking in a low voice, "What do you feel like doing? What do you want to play?" I turned around and answered without hesitation, "Let me tell you," I began. "Actually, my preference is for women, although I'm open to other options. I'm not usually with men, and when I am, they're trans." Before I could say another word, he grabbed the back of my neck, pulling me very close, and put his tongue in my mouth, which I obviously reciprocated. With his other hand, he squeezed my butt with relative force. "So, you're going to let me play with this?" My response, after smiling, was to nod. He continued, "I want to see what you can do with that sweet mouth of yours," he said. That smile, the one that comes from a mix of nervousness and curiosity, returned to my face. Then we heard footsteps; it was the skinny girl coming to find us.
She entered the kitchen with an expression that's hard to describe, saying in a mischievous tone,
"I see someone here is going to have a good time. Just thinking about it is getting me incredibly turned on."
To clarify: The skinny girl's partners are usually women, but she's not averse to a good cock when she's alone. She's quite the sex fiend, like me. That's why we get along so well. I'll share some experiences I've had with her another time.
Continuing where we left off, we returned to the living room where we continued drinking and a little more. After a while, Jon and I were engrossed in some trivial conversation when the song that was playing ended. As the noise stopped, we heard some moans, and that's when we realized they were gone. We went to the bedroom, and there they were. On the bed, still partially clothed, but so engrossed in what they were doing that they didn't notice us watching. I have to admit, the scene was unforgettable.
He positioned himself behind me; I felt his breath on the back of my neck. He pressed himself against my back as he began to give me soft bites on my neck. I would have liked to continue watching them, but he pulled my arm, leading me to the other room.
He pushed open the door behind us and pounced on me. He took off my t-shirt, then his own.
*One more small clarification. I'm not a young man, I'm 53, although I'm quite well-preserved, partly due to my build, since I'm mixed race, and partly because I've played sports for most of my life.
We kissed again, this time quite intensely. Then he sat on the bed and, with a gesture, suggested I do the same. He began,
"Okay. What do you want us to do? Or are you going to let me do whatever I want?"
"That depends," I replied.
- The continuous - If you let me, I'm going to eat you all up, including that sweet little ass. And he smiled.
- Be careful what you wish for. I replied. You might be scared by how much I let myself go.
We kissed again. He stood up, took off his pants, and holding his cock in his hand, said, "Do you want this?"
Without saying a word, I brought my face closer and began to slowly run my tongue over it, circling it completely before taking it into my mouth. I felt it growing little by little. He sighed, sat down on the bed, I knelt between his legs and continued sucking him. When he pushed my head down, shoving it all the way to the back of my throat and saw that I could take it, he said,
- Damn, you sure suck it well.
A pause while we finished taking off our remaining clothes, then we lay down on the bed. We stayed in the 69 position for a while, both of us sucking each other. He was underneath me, and without taking my cock out of his mouth, he started running a finger around my hole, which turned me on even more. He pushed me slightly as he sat up, leaning his back against the headboard, leaving me on my knees, perpendicular to his body. He said, "I want to see you suck it." Of course, I continued.
I heard him spit on his hand, then his wet fingers playing with my anus. Slow, gentle movements, more like caresses. At times applying light pressure, then more caresses. He made it so I couldn't help but move my ass as if searching for his hand, and couldn't hold back the occasional sigh.
He pushed me again, this time behind me. The next thing I felt was his tongue, the incredible sensation of him running it over me repeatedly. He inserted a finger, causing a stifled moan, and with his other hand, he squeezed my cock, gently masturbating it. Alternating between licks, spitting, the occasional slap, and finger insertions.
"Do you want my cock?" he asked. "Do you want to feel it? Do you want me to fuck you like a whore?"
My answer was yes, but a yes as if with it, the little strength I had left would escape from my body. Notice how he rubbed it all over the area. It wasn't excessively large, though somewhat thick.
"Well, beg me for it, bitch!" he declared. "Come on, ask me! I want to hear you say you want me to fuck this little ass."
It was impossible to hold back any longer. As if seized by desire, almost with a shout.
"Yes. Please, put it in me now."
He let out a laugh. "Okay, I'll oblige you, but only if you're a good little slut."
He thrust in, softening a bit after I asked him to be gentler. Little by little, he entered, initially a bit awkwardly because, as I mentioned before, he was rather thick. To make it less uncomfortable, I lay back comfortably, feeling the weight of his body on my back. He continued to gently insert it, and by the time it was fully inside, his movements were rhythmic and deliberate. We had reached that point where, from then on, everything is pleasure.
Absolutely. Inevitable sighs and moans escaped us both. Pressing his face close to my ear, he murmured,
"Do you like it like this, you little slut? Do you want me to continue?"
He increased the rhythm of his movements, as well as the force of his intermittent thrusts, and asked again,
"Tell me, bitch? Tell me if you like it like this. This is what you wanted, isn't it?"
Between gasps and moans, I answered yes.
"Yes, I like it a lot." Don't stop, please. Don't stop.
But he ignored me, pulling it out roughly, causing me to let out something like a howl.
"NOOO!" Don't pull it out.
"Do you want more? Turn around, I want to see your face while I fuck you."
I pulled my legs up to my knees, spreading them slightly as I lifted one with one hand and with the other guided that hard cock back into my ass. I could feel the sticky wetness that made it slide in easily, noticing how tight it was, causing a slight pain that was infinitely outweighed by the pleasure. That pleasure that, unless experienced, is impossible to describe.
I lifted my legs higher and demanded, "Open that ass wide, you whore, open it like the horny bitch you are so I can fuck you good." He spat. Splashing it on my face, he lowered himself, running his tongue over my lips, a long, wet kiss, without stopping the incredibly pleasurable movement. It felt incredibly good; needless to say, I was enjoying it. Obviously, it wasn't my first time, but it was the first time I'd had a cock that thick inside me.
"You're going to be my whore, right?" She nodded as she answered.
"YES! You can fuck this ass whenever I want!"
Without a doubt, I dare say that was the time I truly felt I had enjoyed it. It dispelled any doubts I had before, making it clear to me just how much I liked it. I don't usually go out with men, nor do I seek adventures with them, only with trans women, which are generally paid services. That encounter didn't change that. I will continue with my varied instincts as an explorer and collector of good times, without letting prejudices or less open minds influence them.
He thrust it in completely again, then withdrew almost completely, and then again. With each movement, I elicited a moan or a muffled cry when he pushed too hard.
I gasped, small drops of sweat falling on my back. I begged him not to stop, almost pleading that I wanted more.
"Do you want me to cum? Do you want all my cum in your ass?"
"Not yet," was all I could manage to say, trying to control my already ragged breathing. I didn't want it to end; the ecstasy it caused was incredible. By that point, there was no pain or discomfort left, only pleasure. Impossible to forget that cock snug against my ass, sliding in and out, each thrust sending a wave of delirium through my body.
"I can't hold back any longer," he said. "I'm going to cum." "Where do you want all my cum?"
"In my mouth," I replied. With a swift movement, he sat up, crawling to the level of my head as he said,
"You want to eat cum, you naughty slut?" He squirted some onto the edge of my lips, a little landing on my cheek before he took it into my mouth. I tasted that viscous, warm liquid. I let some spill out to play with while I continued sucking. He grabbed my chin, forcing me to look up, and licked my face. We kissed passionately. He spat a mixture of saliva and semen into his hand. He turned me around, rubbing it against my ass and thrusting his slightly less erect cock back inside me. I spread my legs wide, pushing back as far as I could, savoring every last bit of his hardness.
Panting, we collapsed, lying face down for a few minutes. I lit that cigarette you smoke so patiently, as if you were going to make it last forever.
After a shower, a beer, and a brief chat, she walked me to the door as I was leaving, but not before asking if I wanted to meet up again.
"Maybe," I replied. "We'll call each other next weekend and see."
We met up a few more times. Not too often, but we still enjoy each other's company.
The next morning, the skinny girl's curiosity was so great that she came to visit me quite early so I could tell her what had happened. Because when they left the room, not seeing us, they left.