Encounters on Craigslist Stirring People Up
Once upon a time, I decided to share a personal experience that I once went through. I'll use the same format as before, making sure to maintain the same length and structure.
The story I'm about to tell you is based on actual events that occurred in my past. Although the names aren't real, the words exchanged and the actions involved are.
One day, while living in a smaller city, I was leading a quiet life. I didn't have many social interactions there since I was straight, married, and afraid of being persecuted for my religious beliefs. Being at home was usually how I spent my time, engaging in various activities like watching porn or playing video games for hours on end.
But during that particular weekend, my wife Angela planned to go visit her parents, leaving me to handle work all by myself. I was a teacher back then, so weekends were often used for preparing materials or marking tests. However, this scenario wasn't particularly unusual for us.
It was the 90s, and Craigslist had personal ads. That's when I came up with the idea to create one to see what else was out there. I was particularly attracted to the idea of cuckoldry and submission, but my wife didn't share those same proclivities. Consequently, I mainly explored man-on-man pornography as it seemed more attainable for me.
My ad looked something like this:
24-Year-Old Seeking a Dominant Man
"My wife is away, so I'm home alone for the weekend. I'm looking for a guy who might be interested in a one-time oral engagement. I prefer someone who is equally clean and healthy as myself, as well as patient since I'm just starting out. I'm in my 20s, 5'5" and weigh 140 pounds. My ethnicity is white, I'm hairless (save for my head), and I'm a nonsmoker. Are you ddf and a nonsmoker? I'm available immediately if you're interested."
I received multiple responses from individuals who expressed interest in the proposal, but most of them didn't fit my criteria. For instance, there was an older gentleman with several folds in his skin that I had to decline. There was also someone my age who was interested in only masturbating together. If I hadn't been given any suitable options, I would have probably accepted his offer. However, my favorite respondent was the most promising one.
"Hi there! I think we could hit it off. I'm a bi top who loves to play with twinks and enjoy a good orgasm. I can come over whenever you're ready, with enough time to clean up first. I'm an excellent teacher and provide great oral action. I've got a beautiful 7 1/2” cock and solid balls for you to lick. Let me know what time works for you."
This response had me excited straight away. The language was flirty, and the confidence exuded by the responder was enticing. It didn't mention many specifics, but it was the tone and promises that drew me in.
Without much further thought, I sent a full-body picture of myself (from my waist down), displaying my shaved and hairless body. I mentioned before that I had always thought I was smaller than I believed. My erection made me look bigger, and the way I took the picture made it appear much larger.
Remembering previous encounters where I found myself excited and hopeful, I couldn't help but hope this would be the one to provide my desired experience.
And indeed, my hopes were not shattered. The respondent sent me a picture of his penis, and upon seeing it, I was instantly aroused. This guy was even more enticing than I could've expected. Although he didn't look like any of the muscle-bound guys in porn, the fact that he had six-pack abs is what truly grabbed my attention. And, of course, his significant endowment made me even more excited. Unfortunately, I couldn't see his face as it was shielded in the picture.
When I replied back, expressing my readiness and giving him my address, he responded with "See you then 😉."
I was overtaken by elation. I leapt up from my desk to prepare. Stripping down, I took a shower and thoroughly cleaned myself, especially focusing on my own manhood. I had to be cautious not to climax as I knew if I did, I might lose my courage and renege (back then, I was still obsessed with gender stereotypes and orientation -- and, although I'm more open-minded, I still keep it securely hidden away).
Following the shower, I took my clothes to the bedroom and placed them in the hamper. I was about to select a wardrobe when I recalled his comment about wearing something of my wife's. My heart was thumping as I ventured from my dresser to my Angela's, heading for the top drawer that I knew contained all her products. We didn't have numerous lingerie options, but I already knew what I was searching for and discovered it. It's not challenging to spot something colored hot pink.
As I extracted my wife's lace teddy (my preferred choice for her), I noticed how delicate it felt. I was worried I might distort it, so I ventured to the mirror to slip it over my head. I found that the midsection stretched a bit to cover my chest and I had difficulty maneuvering my arms through the appropriate places (I mean, this was the first time I'd encountered part of this type of clothing). Once I'd done so, I examined myself in the mirror. I had short hair and a smooth face, but my top half was strikingly feminine -- much like a flat-chested teenage girl -- all I needed was a wig and I may have convinced myself. Unfortunately, we didn't own that type of product.
The peculiar aspect was below my waist. My erection was standing tall and demanding attention. It sharply clashed with the feminine image. Therefore, I returned to the drawer and retrieved her hot pink silk panties. At that time, this was a new type of material -- stretchy to remove the need for any seams (to aid in concealment of panty lines). I pulled them on and attempted to tuck most of myself in -- but the tip of my penis remained exposed. Hidden by the teddy, it didn't appear too awful.
Two aspects struck me as I returned to the mirror. One revelation was that I was evoking someone I'd want to have sex with. However, what surprised me more was that I enjoyed the sensation of her panties. Cool on initial contact, they were so soft and silky. In the recesses of my mind, it unsettled my sense of masculinity, prompting me to disregard my insecurities, writing them off as mere play-acting.
I was nearly prepared to commence. My theory emerged, though: it seemed wise to add a layer of modesty. So, I obtained my wife's fluffy bathrobe. I felt indecent in her lingerie, yet the soft and immensely cozy robe made me feel secure. It was like a combination of my misconceptions about femininity: I was intended to be captivating, even tantalizing. Yet, I necessitated concealment, which the robe accomplished.
I invested the subsequent few minutes pace upon the living room floor, considering what was about to occur. On a whim, I had a wonderful thought -- one that has become a habitual occurrence since. At that point in time, we didn't own sophisticated smartphones, but my wife's Canon boasted a video feature. I searched for it, reinserted the batteries, and carried it downstairs to place on the coffee table. Shortly thereafter...
The doorbell rang.
I burst through the stairs, half sprinted through the kitchen, and unlocked the deadbolt. I peeked through the doorway, ensuring no bystanders could see me. When I opened the door, I was greeted with a smile on that clean-shaven visage. In a soft tone, I asked him to enter. With a smile, he stepped inside and shut the door behind him, leaving a subtle masculine scent.
Since I wasn't interested in idle chatter at that time, I led him across the kitchen and inquired if it was acceptable for us to engage in the basement since it was more secluded and I was concerned with open windows. He calmly replied, "Whatever makes you comfortable."
This was my first green signal. I was unaware that my nervousness, when combined with the vulnerability of wearing women's garments, had me so edgy. However, this comment stuck with me, as the tension in my situation receded. I couldn't help but feel my heart racing as we made our decent down the stairs. I felt as though the robe wasn't adhering to my body because every hair was standing upright.
We ventured down into the basement, and as we stepped inside, he took in the surroundings. There was our TV, the coffee table, and the pull-out couch - all places I had deeply engraved memories. I'm positive he was assessing the area and me simultaneously. He probably sensed my anxiety and intended to ease it.
As we crossed the room, he initiated small talk, asking about my occupation and how long I resided in the city. This continued for about thirty seconds, resulting in us now facing each other. I had my hands nestled in the pockets of my robe when he lightheartedly asked, "So did you wear something particular for me?" I responded, "Yes," but I'm unsure if it was due to being a little girlish or simply nervous. He then questioned whether I had ever worn anything like that before. Once more, I answered shakily with a, "No..." His expression brightened as he grinned and moved closer to me, inquiring if he could see it. I mustered a "Yes" as I retrieved my hands from the robe's pockets.
I was anxious when I removed the cord that kept the robe secured. Together, we swiftly released its grip, unveiling my vulnerability. He gently helped me with his free hand. As the robe slid off my back, it caught onto his palm still on my lower back. He instantly said, "Oh, that's quite the sight." Taking a step closer, he brought a smile back to his face and embraced me. This was another indicator for me.
I once believed sex between men was an exchange where one or both was left unsatisfied or humiliated. I presumed this notion arose from the kind of porn I had viewed. This belief perpetuated my fear. But he debunked that stereotype by being a powerful yet empathetic man. During this time, the thought of "going gay" lingered in my head since I enjoyed his actions. Evidently, I had deep-rooted issues with my sexuality.
He proposed filming our encounter - an opportunity to preserve our memories. He could tell I was interested, so he agreed. The two of us, still standing, found ourselves struck in small talk, me half-naked and entwined with a taller, more muscular man who was already controlling my body without forcing it. His hand on my back intensified, practically drawing me closer to him while seeking to escalate the situation.
Then, the unexpected occurred. With one hand on my back, he asked, "Do you want to see what's beneath my clothing?"
Green flag number three signified a break in my illusion about sex between men. He was "inviting" me, which shifted my perspective dramatically. Suddenly, this was safe, and I felt I could trust him. My mind set aside my preconceptions and prepared for an enjoyable experience. Simultaneously, my hands quivered as my fingers interacted with his belt. I had to carefully pull the belt taut to release the clasp. Then, I moved on to his jeans' button and zipper.
Next, I was in for a shock. As he slid off his jeans from his knees and sat down, he casually tossed them under the coffee table. Unnerved, I got up and sat beside him, mentally bracing myself. We were silent as he lingered in the middle of the couch, making it challenging for me to continue alongside him.
In this position, I felt a bit out of place and off-balance. After settling down on the couch, I unintentionally lost my balance and my left hand attempted to steady myself on his right thigh. He must have sensed my need for space and shifted over. His thrusting motion led to my palm brushing against his erection - marking our first physical encounter. I didn't want to lose this opportunity, so I wrapped my hand around his shaft and started stroking it. He drew me closer with his arm, urging me towards his shoulder. I placed my head on his chest near his shoulder, giving me an easy reach to stroke him. His left hand promptly returned to my lower back.
He seemed intent on prolonging the experience, desiring to go slow and savor the moment. I lay my head on his chest, sliding down it as I worked his semi-erect penis into a more solid state. The blood flow was accelerating, making his cock thicker and standing upright.
My stroking continued, moving down his chest and then his abdomen until my face was only a few inches away from his crotch. I was hesitant at first, so I began by licking the head of hiscock. With a better angle, I moved down to his balls and tried to lick the top of his shaft. However, this proved difficult, and eventually, I just held my mouth open, exhaling warm air on the shaft as I moved up and over the head. Bending his penis, I then licked along the bottom part of his shaft until I returned to the head. Wasting no time, I enveloped the head in my mouth and swirled my tongue around it, mimicking what I'd learned from practicing with a dildo.
His hand slid down my back to my butt. This time, it was my left cheek receiving a firm grasp. This squeeze urging me to go deeper propelled me forward. I could take about four inches or so of his cock at this angle. My grip around the base allowed me to cover the entirety of his cock. With my fingers and spit, I bobbed up and down on his cock, lubricating it.
After acknowledging his desire for a slower pace, I felt like I was reaching my limit. Despite this, I wanted to push myself further. The cock in front of me felt like a massive 7.5 inches - perhaps even larger. All the men I'd been with seemed to be understating the size of their penises.
Still determined to please him, I increased my speed on my bobs up and down his phallus, implemented a messier grip, and loosened my lips. I was trying to thrust my mouth up and down his cock while exploring the boundaries of my gag reflex. Unfortunately, my throat resisted and the familiar "glugh, glugh, glugh" sound resulted as I hit the limit of my gag reflex.
This audible response must have indicated to him that I was submissive and willing to put my comfort aside to serve him. He responded by reaching up, caressing my back, and pulling my hair lightly. This added to the feminine experience and encouraged me to take on a more submissive role. To cater to his desires, I shifted my hand to the base, releasing more cock for my mouth to enjoy. I picked up my pace, making long, sloppy strokes as I pushed myself towards my personal limit.
It was his hand on the back of my head that stopped me from gagging. He wasn't rough - quite the opposite, actually. He gently guided my hair, but there was a clear intent to slow things down. "Let's slow it down," he said. "I don't want to cum too quickly." Hearing him say this was a definite confirmation that he was getting aroused by my attentions. This made me more eager to continue serving him.
Images
- An awkward position on a couch.
- A woman in a submissive pose with a man's hand on the back of her head.
- A woman giving a blowjob in a submissive position.
Headers
- Being awkard in this position.
- Losing balance on the couch and landing your hand on his thigh.
- Confronting first contact in a sensual moment.
Lists
- Mentions of Cock in the text.
- Keeps the same order as in the input sentence.
- Does not add any new elements.
Links
- "Mentions of Cock in the text" link redirects to a fictional page about the subject (inallen.com/cock.html).
Highlighting
- No words are highlighted, leaving the paragraph intact.
"He shoved me aside and said, 'Let's change things up.' Unsure of what he had in mind, I got off the sofa as he stood up. Then, with a tender touch, he applied pressure to my right shoulder with his right hand. I realized what he intended to do. In a brief moment, his cock was in his hand, and I was kneeling between his legs. I anticipated sucking him again but instead, he started smacking my face with his big cock. I had witnessed this but this was my first time experiencing it personally. It was slick with spit, which was now smearing all over my face. He put his left hand at the rear of my head to stabilize me as he continued. Then he moved close to allow his cock to slide up my face. At first, I believed he wanted me to lick the length of it. However, no, he raised his left foot onto the sofa and continued to push my head lower.
Understanding where this was headed, I didn't hesitate. When his testicles reached my view, I observed that they were more saggy than what I was used to. The 'hanging balls' aesthetic. So, I began to lick them, followed by slowly sucking each one into my mouth. I carefully alternated between them. He urged me to put both in my mouth. I suspected my own erection, which at this point was hidden in saturated underwear soaked with precum, might have reacted to this. And true enough, I managed to suck both simultaneously. I stroked the one nut in my mouth while using my hand to accommodate the other. To my surprise, my tongue struggled to slide around the underside of his balls because my mouth was so filled. He applied more pressure to my head. In hindsight, he might have been hoping for 'ball sucking' but I was inexperienced and just missed the cue. Nonetheless, I descended further, and managed to insert my tongue beneath his balls. He released his cock to play with my hair again. I looked up at him. I could barely see around the massive length of his cock and forehead obstructing my view, yet I felt exceedingly submissive. That broad grin and those eyes - eyes that held desire and longing - gazed back at me.
It was at this moment he inquired if I desired to go deeper. I answered affirmatively, but please be cautious since I didn't want to vomit. He responded that there was no cause for concern, that he was experienced and familiar with the procedure. My trust in him grew the more he had displayed decorum. So, I declared my confidence in his abilities.
He removed the pillows from the sofa and placed them at one end before instructing me to lie down. I doubted this would function due to the angle. After all, I had previously experienced a man sitting on my face to allow me to suck his balls, but I could only take the tip of his cock in my mouth due to the angle. Thus, I was astonished when he approached the end of the sofa, grabbed me under both armpits with his hands, and pulled me half off the sofa. His only instruction was 'just lay back'.
I understood. The pillows weren't for my head. They were for my back. With my head between his thighs, the armrest - that was for my neck. As he instructed me to relax, I slumped my head onto the armrest, suspended there. This was exhilarating because now I was unable to detach his cock. I was restrained. He separated his legs and advanced - his balls on my lips as I engulfed one, then the other, and then retracted them. As I recollect, he was talking to me, yet with my head where it was, betwixt his thighs, I'm uncertain what he said. I appeared to respond with a hum, indicating my willingness to continue.
He stepped back and nodded before plunging his erection into my mouth, causing it to expand. I twisted my tongue around the head, just as I had when I was performing oral sex on him in his lap before. However, this time, I couldn't regulate the depth, the rhythm, or the twist. I held my hands interlocked atop my chest, the teddy I wore accentuating my feminine appearance. Meanwhile, I serviced a man. A man who was now in control of the entire scenario. Was he about to fuck my face? Would he force himself so deeply that I would struggle to breathe and generate heaves? Could I vomit?"
In my mind, I was struck by a sudden shift when he started. He wasn't shoving it in my mouth; there was no skull fucking. Instead, his dick glided across my tongue, back and forth. Saliva started building up. He gradually went deeper each time until I felt my gag reflex kick in, "glugh" as before. However, this time it wasn't a poke but pressure. It wasn't extremely firm, but it was present.
Now that I wasn't trapped beneath his legs, I heard his next command, "relax, we're just going to stay like this." Then, each time he pushed down to my limit, he held it there. At first for a second or so. Then, a few moments later. But then, it kept getting longer and longer each time.
Then I realized I was panicking and slowly starting to calm down. That he knew more about my body than I did. The feeling of trust intensified, and I acknowledged that he held himself at my gag point for so much longer - maybe close to eight seconds. He then simply said "breathe." So I did. Breathed with the cock all the way down my throat.
From my perspective, I could see his nuts, just a few inches away from my eyebrows. I could see them move away and towards my face as he retracted his dick and thrust it back in my mouth. He held himself there lengthily this time. I wasn't panicking. I was chill and relaxed. And then, it finally happened.
I didn't expect it at all but could hear him murmur, "oh yeah there it is," as those nuts, which had been hanging in front of my face, were suddenly right beside me. My nose was covered in that fleshy man meat that suspended them. I realized that with the right technique and the right level of patience, my throat had turned into a new zone to investigate. He had been granted access due to his patience with my inexperience. He withdrew and questioned if I enjoyed it. I confirmed, saying yes. I then released my hands, grabbed his ass on both sides - just like he did to me - pulled it towards me, and positioned his nuts on my face. I felt spit leaking out, down his balls, dripping onto my cheeks (or was it up?). We repeated this process a few more minutes. I adored every bit of it. The spit just kept coming. Soon it was running over my eyes as well, sticking to his nuts which were lightly prodding my face. It was fantastic. I felt so filthy - yet I was still feminine. I couldn't quite put a finger on this feeling - but I loved it.
He chose to step back, took hold of my head, and guided me to sit up straight. At that moment, I realized how messy I had become. My face was covered in a thick, sticky substance. I had no clue if it were mucus or vomit; it had undeniably been combined with my saliva. He proclaimed, "Sexy." Then he asked me, "So you want to record a video now?"
I momentarily forgot about the camera, but instantly agreed. I grabbed it, turned the display towards me, activated the video mode, and placed it on the coffee table. He asked for my preferred position. I suggested the same one but in the middle. So I laid on the couch, lifted my feet up onto the backrest, and turned my head to the edge to get ready for the porn we were about to stage. I left my face in that awkward position in anticipation of the grand finale of our nakedness.
The video we created was merely a few minutes long. Warmed up and all set, he knew my jaw was beginning to ache (he had seen me stretching and massaging it when I stood up), so he was ready to execute the climax.
The video provides a unique outlook. When watching it back, it felt like I was observing someone else. It showed a young guy dressed in pink lingerie on the couch. The video commenced with a man's legs appearing. He was naked and erect. He dropped to a low stance so the boy could suck his dick. The boy, who was powerful, took two measured thrusts. You then see the nuts land on his face. The grip on the man's ass by the boy's hands is noticeable but not in sync with the man's movements. His eyes focused on the camera as spit flowed from his face.
The boy is deliberately sucking the man's dick, not an accident. His hands pull the man in, and after the man pulls his dick away, he brings the man back in again. The boy clearly wants the dick in his throat. You can tell he's initiating the thrusts, ahead of the man's movements because he's setting the tempo. The pace starts to quicken. It was a few seconds between thrusts before, now it's just like a clock ticking. Tick. The dick is fully in and out again. Tock. The balls swinging make a slapping sound as they hit the boy's face. The boy is being pounded into the couch and as he slides up from the barrage, the man's balls obstruct the view of the boy's eyes. The only thing visible is a large blob of spit dripping down each side of his face as the speed increases.
The boy is skillful. His face is drenched in spit. Long strands droop to the ground. But he doesn't choke. He doesn't cringe. He's probably an expert at this. Then the man's hands appear, gripping the boy's wrists. Not in a gentle manner like you might hold someone's hands, but taking hold of his wrists as if he owns them.
The hands disappear from the frame as they go behind the man's body, in front of him. Only one returns, loose and laid back, then placed on the man's hip.
The man's tempo remains the same - as if he's thrusting from behind, not the boy's mouth anymore.
At this pace, the man starts to moan. With a few forceful thrusts, it's evident he's filling the boy's throat with a load since he grounds his dick there and moans. There's a prolonged pause. No sounds or activity except for the ball sack pulsing, ejecting a load into the boy's throat. Then the boy's right foot jumps once. The man and boy remain stationary in that position - twenty to thirty seconds. The boy's feet begin to move - as if trying to escape, like he's trying to breathe. As the man pulls away, he moves to the side, revealing the boy with a messed-up face, gasping for air, coughing out a clump, more cum flowing down his spit-soaked face. Yet, it's the hands in the shot that are thrilling. You can see that the boy's wrists are crossed, and both are held tight by the man's left hand. And he's trembling. Not from fear but from pleasure. Until then, we didn't know what was happening outside of the view, but it's obvious the boy was merely a tool for the man to ejaculate into his throat. At that moment, the boy's pleasure was secondary - it was all about the man's satisfaction.
The man chuckles and asks, "So, what did you think?" The boy struggles to answer and says, "Perfect." You can tell he had difficulty expressing himself, his face a wreck and his nose clogged with spit and probably some cum. A cum bubble forms on one nostril as the boy tries to wipe it off.
The man approaches the camera, with his drooping and sticky dick the final frame of the video. The video omits the aftermath. Mr. Clean complimenting me on my performance as I wipe a tangled mixture of sperm, spit, and snot from my face. He instructs me to use it. "Use that mess to lubricate your dick and cum. You earned it."
I don't need to be told more. At this point, I feel used, like I'm a sex doll. I scrape a decent amount of that gunky mixture off my face and stuff it into my silk panties and start stroking. He joins me and offers me his cock once more. It's limp now but that's a new experience. It's slippery and limp so I suck it up like a big spaghetti noodle and just keep it in my mouth, my tongue licking his balls. Both of his hands grip the back of my head as I tremble. Once more, I can't breathe due to my face being sealed against his pubic area.
I'm intensely aroused, feeling hot and horny. I might have managed ten strokes before I profuse a massive load. I'm completely covered in cum and spit.
Now, the internal inhibitions resurface, and I realize I'm garbed like a feminine, totally drained. I'm soaked in my own spit and Mr. Clean's semen. My mouth and jaw ache, and my throat is lined with sperm, all caught on camera like a prostitute.
He knows it's time to leave, heads to the restroom to wash up, put on his clothes, then climbs the stairs and exits the building. His final comment is a sarcastic, "Thanks for letting me teach you a lesson." accompanied by a beaming smile like Mr. Clean.
After he leaves, I remove my clothing and shower, using approximately twenty paper towels to clean up the mess (the puddle was around 18 inches wide). I toss my wife's undergarments into the washing machine and remove the camera card, save the video to a clandestine folder on my computer. I put the camera back, check twice to ensure no traces of my actions remain, and then watch the video I recorded.
What transpired that day was the most arousing thing I've ever done and witnessed. I prefer homemade pornography to strangers online, and this is better than anything I've ever produced. I watched that video three additional times that day, masturbating during each viewing.
Slowly, my perspective shifts. Perhaps I've come to comprehend homosexual play. Maybe bisexuals exist on a spectrum, with some being so strongly attracted to one end that they cannot fathom the other. However, despite this, gender and orientation assumptions seem less relevant. I must be somewhere in the middle with fantasies that revolve around activities rather than gender identities.
I gained insight on several levels that day. I learned to endure the gag reflex through tolerance and with the appropriate partner. I realized that I should evaluate my fantasies based on the activities and the individuals involved, rather than their gender. And finally, I discovered my attraction to humiliation, submission, and fantasies when I can keep them hidden. Reveal
