Craigslist Encounter Awakening

Like most of my stories, this story is based on one of my earlier experiences and is factual. Names are never real but the conversations and activities are authentic.

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So this story takes place when I lived in another city (a smaller one where there were not many options for a straight married guy living in the closet and under fear of religious persecution). My activities were not varied by my appetite for new stories and videos had me on the internet whenever I was home alone (which wasn't often so I went hard when I had the opportunity -- often masturbating multiple times watching porn, or generally just playing video games all day).

As fate would have it my wife Angela had taken our sons to visit her parents a few hours away and would be gone for the weekend leaving me to work. I was a teacher at the time so weekends would often be spent developing materials or marking tests so this was common for us though not often.

Back then Craigslist still had personal ads so I decided to drop an ad as I often had done before -- to see what conversations I would have. At the time I was fantasizing about cuckoldry and submission, but as my wife didn't have the same sexual proclivities I ended up watching mostly man on man videos because I thought it was a more feasible fantasy.

So I posted a few ads but the one that worked out in the m4m section went something like this:

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**24M Seeks Dominant Dude**

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"My wife is gone and I'm home alone; just wondering if there are any guys that might want to come over for oral only. I want a guy that is clean and healthy like me, but is patient because I'm kind of new to this and want practice giving head. I'm 24, 5'5", 140 pounds. I am white, clean, ddf, shaved hairless, and a nonsmoker. You need to be ddf and a nonsmoker like me. I can host anytime today but the sooner the better."

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I had a few instant replies. I politely responded asking questions about them but when they didn't fit my need I declined them. One was an older much bigger guy that I declined (I don't like the smell or test of guys who have folds in their skin). One was a guy my age but only wanted to masturbate together. If it was the only prospect then I would likely have taken him up on the offer. But the one I chose was the best response of all.

"Hey I saw your ad. I think we could click if you took a chance with me. I'm fully bi and top, love to play with a twink and bust a nut. I can come over whenever you would be ready, just need to shower up first. I'm into oral sex and I'll give you some practice. I'm patient and a great teacher. I have a great cock and decent loads. Just pick out something of your wife's to wear and let me know what time."

Now that alone was a pretty decent opening message even though it didn't have any stats. So I replied with a picture of me. It was a picture I had taken a couple of years before, from my waist down showing me completely hairless with an erection. I always thought I was on the smaller side. I told myself and others that I was six inches, but that was when measuring to the base on the side not the top. My upward bend meant I was likely slightly less. But it was cut and the way I took the picture with my Angela's camera made my dick look bigger than it was.

Now I did think to myself that I've been in this situation before, having a hopeful conversation that something would become something more. Instant erection, precum in my underwear, hoping my response would get me what I hoped for.

I wasn't disappointed. I got the response a few moments later. He told me he was 39, 5'10" tall, 195 pounds, married like me so he was always discrete, white with a shaved head and a cut 7-1/2" cock ready for me to suck on and nice balls to lick. He attached a picture this time and boy did that set me off. I was immediately horny and wanted to serve this guy, this Mr. Clean -- "esque" guy. He wasn't ripped but he had abs, but the part that got me was what was below. His dick was like mine, cut, strongly erect, clean shaven but the difference was obvious -- it was bigger than his hand (significantly bigger). His face was blurred out but I could see that clean shaved head like Vin Diesel.

I couldn't respond quick enough. I said I just needed a half hour to prepare and shower up. I gave him my address and sent off the reply.

He replied right back with "See you then. 😉".

I was launched into euphoria. I leaped up from my desk to get ready. Stripping down I got into the shower and scrubbed myself head to toe thoroughly with special attention on my own manhood. I had to be careful not to cum because I knew if I came I might lose my nerve and back out (back then I was still hung up on stereotypes of gender normativity and orientation -- and even though I'm more open minded I still keep it firmly in the closet).

After the shower I took my clothes to the bedroom and put them in the hamper. I was about to pick out clothes and then I realized what he said about picking something of my wife's to wear. My heart was pounding as I went from my dresser to my Angela's, opening that top drawer that I knew she kept everything in. Now we didn't have much lingerie to pick from but I already knew what I was looking for and found it. It's not hard to spot something that's colored hot pink.

As I pulled out my wife's lacey teddy (my favorite for her to wear) I realized how frail it felt. I was worried I might stretch it out so I went over to the mirror to pull it over my head. I felt the mid section stretch a bit to get over my chest and I had trouble getting my arms through the right spots (I mean this is the first time I ever had spaghetti straps on). When I was done I looked in the mirror. I had short hair and a clean shaven face, but my top half really did look feminine -- like a flat chested teenage girl -- all I needed was a wig and I may have been able to convince myself. I wish I had one because we didn't own that stuff.

The part that was weird was below the waist. My erection was standing proud and needing attention. It really contrasted the feminine aesthetic. So I went back to the drawer and found her hot pink silk panties. Back then this was a new style -- stretchy material so that it needed no seams on the edges (to hide panty lines). I pulled them on and did my best to tuck most of myself in -- but the head of my dick still peaked out. Hidden by the teddy it didn't look too bad.

Two things struck me as I stepped back to look at the mirror again. One was that I was looking like someone I would want to fuck. But the other that surprised me more so, was that I liked the feel of those panties. Cool when they went on, they were so soft and silky. In the back of my mind it nagged at my masculinity and I dismissed my inhibitions on the pretense it was just roleplay.

I was about ready to get to business. It struck me however how vulnerable I would feel greeting my guest at the door, so I grabbed my Angela's fluffy bathrobe. And that completed it. I felt naughty in her lingerie, but the soft and uber plush robe made me feel comforted. In the back of my mind I was embracing my misconceptions of femineity. I was supposed to be attractive, even seductive. But I needed to conceal it modestly -- which the robe did well.

I spent the next few minutes pacing the main floor back and forth. Thinking about what was going to happen. Last minute I had a great idea -- one that I've utilized many times since. At this time we didn't have smart phones with decent cameras, but my wife's Canon had a video mode. I went and found it, changed the batteries and took it downstairs to the basement to put on the coffee table. Then it happened.

The doorbell rang.

I erupted up the stairs from the basement, half sprinted through the kitchen and unlocked the deadbolt. As I pulled the door open I stood behind it and peered around. I didn't want any passersby to see me. When I opened the door I was greeted with a smile on that Mr. Clean face. I softly asked him to come on in. With a smile he stepped through the threshold and closed the door behind him, a hint of a manly scent. Cologne? Body wash? I wasn't certain, but I noticed he had nice shoes (like somewhere between casual shoes and dress shoes), clean tight jeans and a t-shirt which showed his muscles -- those pectoral muscles that a healthy man has.

I wasn't into small talk at the time so I started to lead him across the kitchen as I asked if it was okay if we play in the basement because it's more private and I don't want to worry about windows. He calmly responded with "Whatever makes you comfortable."

This was green flag number one for me. I didn't realize that my nervousness, combined with the vulnerability of wearing woman's clothes had me so on edge. But this comment sticks out in my mind because the stress of the situation began to taper off. I felt like my heart was going a million miles an hour as we made our way down the stairs. I felt like the robe wasn't clinging to my skin because every hair was standing up on my body.

As we got into the basement he saw the surroundings. Our tv, our coffee table and the pull out couch where my memory of the day would be etched. I think he was taking stock of both the space and of me. I'm sure he sensed my timidness and wanted to ease it. As we walked across the floor he started the small talk asking what I did for a living and how long I had lived in the city. We did this for about thirty seconds which meant we were now standing facing each other. I had my hands in the deep pockets of the robe when he casually asked "So did you put on something for me?" I responded "Yes" -- likely in a girlish response not because I was that way but because I was so nervous. He asked me if I had ever worn something like that before. Again I responded timidly with a "No..." His face broke out in a big smile and he stepped closer to me as he asked "Can I see it?" I must have been so nervous because he knew it. He put one hand on my lower back as he got close. I said "Of course." Lifting my hands out of the robe's pockets I went to the rope that held it closed to untie it, to reveal my vulnerability. As I tugged at the rope he helped me with his free hand. The rob fell open and I shrugged it off my back. It caught on his hand which was still on the small of my back. He immediately responded with "Oh now that's a pretty thing." With a big smile he pulled me close to him. This was actually green flag number two for me.

I always thought that sex between men should be an exchange, one or both getting off at the detriment or humiliation of the other. I suppose this fantasy came about because of the style of porn I watched. This misconception just fed into my nervousness. But he shattered that preconception by being a strong dude with a sensitive disposition. I remember thinking that I was worried that I was 'going gay' because I liked it. Obviously I had some real psychological hang ups about my sexuality.

He asked me if I was wanting to film it -- to keep any memories. He'd obviously seen the camera and knew what I was hoping for. I said if he was okay with it I would enjoy that. He said he would be happy to do it. I think we were starting to make small talk, me in that teddy and panties, in front of a taller, stronger man who was already beginning to control my body just with that hand on my back. He reached down with his other hand. I presumed he was going to pull me closer but no -- not the case. His hand went lower as he stooped down, pulling his head down to my shoulder somewhat with that hand trailing down my shoulder and my back. He continued until his hand was on my butt and then did something no guy ever did before -- he squeezed. And not like a little caress -- no it was a handful. I felt like he was literally taking my whole ass in his hand, like he could lift me up and put me on a shelf. Obviously my imagination was getting vivid.

Then he just casually asked "So do you want to see what's under my clothes?"

This was green flag three for me. Like I said my hang ups about sex between men is that it was an exchange, usually one where a guy just offers up his dick so the other guy can service him. But this was different. He was 'inviting me'. From my memory it was this moment that I decided that this was safe, that I could trust him, and that I was going to just let go and enjoy it.

I hadn't responded to his question. I mean I really didn't need to. My hands were speaking for me. While he held me he leaned back a bit as my hands fumbled at his belt. I had to tug it taught to release the clasp. When I did I immediately went to the button on his jeans. He dropped the robe and reached his hands across his body and with both, began lifting his shirt. He revealed his abs -- and I tell you -- they were firm and ribbed. Even better than the picture. By the time his shirt was off and casually tossed on the coffee table I had the button and fly on his jeans down.

It was now that I had my surprise. As he pulled his jeans down for me his already semi-erect cock emerged (no underwear to be seen). It was just as I imagined it from the pictures. I love when products are as advertised and his looked like mine -- just bigger but proportionally the same.

As his jeans got past his knees he sat down on the couch to finish taking them off. Casually flipping his socks on the pile he pushed my robe and his clothes under the coffee table. While he sat down I was starting to mentally prepared myself. I worried that I wasn't going to be good enough for him -- that I might not satisfy his need. Needing to get psyched up I decided to kneel on the couch next to him. There were no words. He had sat down in the middle of the couch and being that it wasn't a particularly long couch that didn't leave too much room for me.

Being awkward in this position I was a bit off balance. Once I got on the couch I lost my balance, my left hand trying to brace myself landing on his right thigh. I think he realized I needed the space so he shifted over. In doing so his cock traced across my palm - and there it was: first contact. And I wasn't about to let it go. I grasped that cock in my left hand and began to stroke it. He pulled me with his arm to his shoulder. I guess he was hoping to take our time, to go slow and enjoy it. I rested my head on his chest just below his shoulder so I could easily stroke him. His left arm immediately went back to the small of my back. I began to slowly lower my head, sliding down his chest as I stroked that already semi-hard cock to life. I could tell the blood flow was coming because his cock was getting thicker and was pointing straight up now.

As I stroked I continued to slide down his chest and then his abs until my face was resting right in front of his dick. And then I started. First with a few tentative licks of the head, then adjusting my position I went down to his balls and tried to lick up his shaft. I couldn't because of the angle so instead I just held my mouth open, exhaling warm arm on the shaft as I moved up and over the head. Bending his cock away I went to the base on the belly side and started licking up his shaft till I got back to the head. No more dancing around, I popped that cockhead into my mouth and began swirling my tongue around it clockwise and then counterclockwise. I was trying to get him wet like I found helps when I practiced on a dildo.

I feel his hand slide down my back to my butt. This time it was my left cheek getting the firm squeeze. That firm squeeze pulled my body forward -- like it was urging me to go deeper. And so deeper I went. I took him as far as I could in that position -- which I wager was four inches; maybe a bit more. My hand now gripping the base I could cover his whole cock this way. I began to bob up and down, trying to lube up the shaft with my spit.

I could tell he sensed as I was at my limit but wasn't being aggressive about it. I felt a bit bad actually because I thought I could manage more. But that cock felt like a big 7-1/2". If that's what it really was then some other guys must have been lying and him honest because this was the biggest I had had to date.

More squeezing my ass, more bobbing up and down on that cock. I knew not to swallow my spit but to let it drool down his cock. I was working up a good amount and could now use my hand too. I relaxed my grip to let the spit work my fingers and his cock, then gave a couple of twists to spread it around. With a relaxed grip I resumed my bobbing but added my fist into the action.

It was this moment I felt that left hand ride back up, rub my back in a couple of circles and then it came up higher, resting on the back of my head.

Now I've had a couple of different guys with their hand on the back of my head before -- one was too aggressive and another just left it there like a limp noodle. But my Mr. Clean did something different. He played with my hair. It added to the feminine experience I had going and now I leaned into it more. I wanted to perform for him like I see the women in porn do. So I relaxed my grip and moved my hand all the way to the base, freeing up more of his cock for my mouth. And then I started it. A faster pace, a sloppier relaxed lip -- I was trying to fuck my mouth with his cock. And I was trying to push my limit. I felt my throat resist as I tried to make my fantasy happen -- but it wouldn't. Instead of getting past that point I was just constricting, making that all too familiar "glugh, glugh, glugh" sound as I hit the limit of my gag reflex.

This was obviously the sign to him that I was here to be submissive, to willingly put my comfort to the side to try and serve him. His hand grabbed the back of my hair and pulled it up. Not aggressive - don't get me wrong. But it was abrupt. What he said sticks out in my mind "Let's slow it down. I don't want to cum too quick."

Affirmation! I was doing it! I was getting his rocks off -- which just made me want it more.

He pushed me off saying "Let's switch it up." Not knowing what he meant I got off the couch as he stood up. Then with a gentle hand he pressed down on my right shoulder with his right hand. I knew where he was going with this. In a moment his cock was in his hand and I was kneeling between his legs. I opened my mouth to suck him again but instead he started slapping my face with that big cock. I had seen this but this was the first time for me that a dick was literally slapping my face. And I was enjoying it. It was covered in slobber, which was now spreading around my face. He put his left hand on the back of my head to steady me up as he continued. And then he leaned forward so his cock was sliding up my face. At first I thought he wanted me to lick the shaft up and down. But no -- he put his left foot up on the couch and continued to press my head lower.

I knew where this was going and wasted no time. As his nuts came into view I noticed that they were more droopy than I normally see. The classic 'hangers'. So I began to lick them and then slowly sucked the one into my mouth, and then the other. Back and forth as his dick was taking a break from my ministrations. He encouraged me to put them both in my mouth. I think my own erection (which by now I was aware was sitting in wet panties soaked with precum) lurched a bit in anticipation. And by golly I did it. I sucked the one nut in my mouth and then stuffed the other with my hand until I quite literally had the biggest balls I'd played with filling and stretching my mouth. I tried to caress them with my tongue but it was difficult to slide it around the underside just because of how full my mouth was. He pressed my head a bit lower. In retrospect he may have been hoping I was going to toss his salad but I was new to this and just missed the clue. But lower I did go, and I was able to push my tongue in and out on the underside of his nuts. He let go of his cock so he could play with my hair again. I looked up at him. I could barely see around the cock that was resting on my face and forehead, but I felt so submissive. That big Mr. Clean smile greeting me -- those eyes -- eyes with desire and anticipation.