Experience popping my cherry with my dad’s friend… [Mm] [anal]

I wanted to share a story of an experience I had when I was younger involving me popping my cherry with one of my dad’s friends. I kept this story bottled up for a long time thinking it was weird and embarrassing, until I finally told a friend recently. He found it sexy and told me he was jealous, which motivated me to post it here. Regardless, I hope it helps to take some of the shame away from something that is supposedly common, and maybe show some people out there that it isn’t wrong to explore your sexuality with someone more experienced

My sexuality started budding late for a somewhat jock-type guy. Whenever boys in the lacrosse locker rooms shared nudes of girls or talked about their middle-school sex experiences like hand-jobs and making out, I felt uncomfortable. Like an outsider. Whenever they tried to hook me up with girls I would say I was waiting for marriage or something to hold them off. I was ribbed constantly for it.

I finally broke to the pressure when I was 14 and made out with a girl who had a huuuge crush on me, at a summer party. The experience was painfully awkward since I was shy and she had to initiate everything while I just kinda played along. I will spare the details but it ended with her pulling out my flaccid penis, failing to get me hard, and leaving the party in tears. That was the last time I ever tried to get with a girl. I pretty much realised I wasn’t into girls at that point and almost immediately the whole school caught on. I was never overtly bullied for it, but I felt weird and out of place, so I became more reserved and tried hard to forget about the whole thing.

I luckily moved to another state that September, so the endless rumors about my sexuality were buried at my old school. At my new school, I doubled down on sports, getting somewhat muscular, but lean and still twinky. I spent the rest of my time outdoors hiking, fishing, and camping. I was popular, but shy, which I thought made up for the fact that by senior year I had never had any sexual experience with anyone else (not to say I didn’t indulge with a certain phallic fruit when my parents left ;)) Girls were into me because they thought I was good looking (strong jawline, thin waist, good shape, thick and dark hair), but I always rejected them and told them I liked them as friends. I did occasionally make out with a girl to keep people off my back, but I can’t say I much enjoyed it.

That’s also when I started working with Todd (name changed for obvious reasons). Todd was my dad’s fishing buddy that he knew since he was a kid. Todd owned a successful landscaping company and gave jobs to fit young guys who were willing to haul ass for him. He was a damn good boss. He bought lunch, he brought beer everyone now and again after a long day, and he was out in dirt just like us. Everyone who worked for him loved him. But we had a special relationship. Around him I was never shy. I was outgoing, and joking with him constantly and I saw him as somewhat of a mentor. After a few months of work, I was the guy who he would call first for every job. As he put it: I was his number one guy. I would get butterflies as he said that and clapped my back. He was the first guy I truly had feelings for. Not the timid feelings you have for a cute blonde classmate, but true feelings of lust and desire. I emptied many tissue boxes in bed thinking about him mouth-fucking my virgin lips.

Over my senior year we started to spend more time together outside work. It started with a simple dinner after a shift, and grew from there. My dad was always pretty distant since he flew around the world for work, and pulled long weeks with little rest. In all honesty, my parents were thrilled I had a dad-like role model to look up to and learn from. He would take me fishing to his cabin at a nearby lake, and teach me everything he knew about fishing. Having no sons himself, he loved doing guy stuff and I couldn’t get enough of him.

By the time I turned 18 I fantasized about having a love affair with him. I would lay in bed hard as a rock and imagine him taking me to a hotel room out of town and showing me everything about the male form, exploring my body and teaching me to please him. When I finally blew my load, I felt sinking guilt and disgust. He must have been nearing 50 and had been married to two women, and fathered 3 girls. The thought of him being into me seemed impossible, yet I did everything in my power to turn him on. I worked with my shirt off, flexing my abs and keeping my shorts low so shadows would fill my tight pelvic muscles. I would think about him so much at work that I got hard, and then I would ask him questions and chat while flaunting my barely visibly erect penis through my shorts. Looking back, I don’t really understand why I did it. I had no intention of letting him do anything to me, but the rush I would get from flaunting turned me on more than any twink-bear porn could.

For the longest time, he never once seemed to notice or make mention, until he made a comment one work day when it was just the two of us. We were working on a retaining wall at a large house near his, where this perky college girl just a year older than me lived. In the summer heat, she brought us lemonade and ice to cool us down and tried flirting with me. To show Todd I wasn’t interested I shut her down right away and she went back into the house in her tight, cut-off, short shorts. Todd looked at me and pointed out the obvious.

“Sounds to me like she likes you.”

I denied it and tried to laugh it off but he persisted. He said that she definitely wanted me. Just the mention of sex coming from Todd’s mouth made my libido rage and I told him, “I bet she would rather fuck you. You’re pretty good looking for your age.”

Todd laughed and flexed his bicep jokingly. I knew this was chance to make a move so I pushed any reservation down into my gut and told him, “If I was her, I would fuck you.”

He looked at me for a second and said “It’s a damn shame you aren’t. I would love that.” I looked away bashfully, and when I looked up he gave me a little wink. I nearly made a mess in my pants right then and there, but I managed to keep it in my cock until I got home. For the first time, I actually considered trying to have some fun with him. I didn’t care how old he was or if he would have to look my dad in the eyes the next time they watched football. I wanted to let him to anything to me. I wanted him to make me his princess. Dress me up in lingerie, complement how my ass looked and spend every day together hanging out and spend every night fucking wildly. That week I bought my first toy online, based on what I imagined his cock would be like, and named it Todd. I considered it preparation for his own penis, and tried to get it a little further every time so I would be ready for him.

Just a month before school ended, my dad promised a weekend away the first week school was out for just us two to relax. He promptly cancelled citing a work problem, but told me that if I wanted to invite a friend and an adult chaperone, we could still use the lodge he had rented at a private lake far outside the city. I faked thinking about it and told him Todd might be able to chaperone and another friend could come with us. Todd seemed excited by the prospect of coming, and I never told him about a friend, I said it would be just to two of us. As for the friend, I told my parents I was bringing a flakey friend so it was no surprise when he “cancelled” last minute.

The weeks leading up to it I prepared intensely, using my silicone Todd daily, and looking up ‘sex tips to make your man cum quickly’ online. I also bought two more toys: an inflatable one to open me up, and a plug to keep me ready for my next breeding. I anticipated the weekend to go two ways: having Todd look at me in disgust when I make my move, or fucking so much that my ass would leak cum until the end of summer. But doubt started to make me paranoid. What if he wants to use a rubber and we don’t have any? I ordered a of 32 just in case. But what if these are too small? His bulge was nominally larger than the tiny mound I was packing, so I ordered a case of 32 Mangum condoms for good measure. I also brought two kinds of lube and ordered a couple of lingerie panties in case he wanted me to pretend I was a girl. I had come more prepared for passionate sex than I did for fishing.

But as weeks passed I became increasingly unsure of our relationship. One day he would be telling me how much I have grown up these past few months and how strong I am, and the day after he would be quiet and lost in thought. I thought about cancelling so many times, but even the slightest chance that I might be getting nailed by him forced me not to. By the night before, my pubes were waxed, my supple skin moisturized, and my butt douched sparkling clean. I fell asleep that night dreaming his thick arms were around me.

I woke up early, and put my new plug inside myself. Walking around felt funny at first and I had to hold my erections down because every movement accentuated the sensation of having something inside me. The remember the drive up being full of innuendo. He asked if I was excited and I told him, “You have no idea.”

“I think you are going to learn a lot. Fishing is a man’s sport, and I’m going to teach you a lot this weekend.”

“I hope we do it a lot,” I told him as I felt my piece rising in my pants, “I have been dying to go fishing for a while.”

“Don’t you worry. We’ll be fishing all weekend, bud.” He assured me.

What I saw as subtle innuendo continued the whole ride and I could tell I was becoming visibly nervous, but Todd remained calm as he always was. When we launched the boat and got out onto the lake, Todd cracked me a beer and started fishing. It was mid-day so it would be a while before the fish started to bite, which gave me time to start testing Todd to see how far we would go. The conversation started off light, about fishing and general small talk. Then we started to get personal. He told me stories about him in college and high school, and I would try to one up him with my own stories. I loved asking him personal questions and having him answer with advice. In turn, he would ask me personal stuff and so on. Kind of like a game of truth or dare, just without the dares. Any kind of personal talk with Todd always turned me on, and being a horny high school boy, I started to get erect.

Any subtlety about me having a raging hard-on for him ended right as he took his shirt off. I looked at his lightly furry chest, so broad and thick. His gut was tight and his shoulders were wide and rounded with muscle. I had always admired his hard, square cut jaw and rugged stubble, but now I was checking him out from top to bottom as he looked right at me. He really was a man compared to me, as at the time I could barely grow chest hair. I bit my lip and looked up to him submissively as porn had taught me all good twink bottoms do.

“Can you put sunscreen on my back?” I asked innocently, “I have trouble getting it low.”

Without saying anything I felt myself go hard again and tensed my cock up in my swim shorts so it would be visible. I wanted him to see it so bad. Without even hesitating he took the sun oil and told me to lay down flat on my stomach. It started as regular sunscreen spreading, but quickly turned into a massage. I told him it felt good and I asked him to massage harder to get the stress out. To my surprise, after just a few minutes he climbed on top of me and started massaging me deep. As I let out sighs of pleasure, moved down slowly and sat basically right on my ass while gently rocking his body, caressing me under the pretense of a massage. I started to feel him work on my lower back and glutes and he was definitely getting hard.

We continued our personal conversation.

“You ever been with a man before?” he asked me.

I shook my head. “Not yet.”

He started rocking harder so my cock was rubbing against the seating of the boat through my shorts. He got gradually faster until I could feel him rubbing his manhood hard against my butt. He asked me if I liked it as he sped up and began to feel up my butt. I replied by moaning and telling him not to stop. As it when on and became hotter and heavier, I was gradually working up towards finishing all over my pants. Before I could tell him to stop so we could move on, I felt my body tense up for orgasm, and I creamed a giant load right into my thin, pink, swim shorts. I knew he could feel me cum because he started slowing down and dismounted me.

“Holy fuck I think I just came,” I told him, turning over. I was mortified at first, but he found it cute realizing how inexperienced I was.

“Let’s get you out of those trunks and have some more fun,” he told me, and I took them off and sat in his lap facing him. He kissed me on the mouth firmly, caressing and feeling me harder now and rubbing my plug. Due to my in-experience my hands just stayed gripping his back for balance.

“Touch me you little faggot,” he told me assertively, but with passion. Right away I remember getting off of his lap and slipping to my knees with both hands caressing his bulge. I unzipped his pants, eager to see his endowment for the first time. To tell the truth, it makes me feel inadequate to this day. It was like a boy compared to a man. I don’t consider myself small by any stretch, just average at maybe five and a half inches. But his was a solid half inch bigger, and much thicker and heavier. It was darker than his normal tan skin tone, and beautifully uncut. I had always wanted a big uncut penis like his. It made me feel tiny. On top of that he was not even fully hard (as an older guy it took him a while to get erect sometimes) so at that point I did not have a clue how big it actually got.

His skin was pulled back under his head and his tip was covered in clear pre-cum. I put my tongue out and sucked it all off of him and started to move my mouth over his cock, not really knowing what I was doing. He must have understood this because he started giving me instructions like “lick my balls now” and “go deeper.” Although I initially hesitated, I responded to all his requests with “yes, daddy” in my most submissive voice. It felt right and it showed him what kind of dynamic I wanted. I must have really sucked at blowing him because after half an hour he told me not to tire myself out and we started kissing again. He was the most handsy person while kissing. He rubbed my bottom, touched the inside of my thighs, stroked my cock, played with my balls, and toyed with my nipples while I sat there like his play-thing.

We both took a breather after a while and started to talk about how we felt. I gushed about everything to him. My silicone toy named after him, my preparation for the weekend. He offered to pay for all the condoms I bought and yes, the magnums fit him best (we tried them on for fun that night and now I know for a fact that I don’t have a big dick). He told me he had wanted me for a long time too, but fought the urges until now. He told me he had never intended to fuck me this weekend had I not initiated. As I looked into his eyes I felt love for the first time. I was obsessed with everything about him.

We did a little photoshoot on the boat that day, which helped my confidence. He told me I was a perfect bottom while bending me over and taking pictures of me spreading. We filmed a video of me giving him a blow job, and I made it kinky by deep-throating him until tears streamed down my face. We must have taken over 200 photos that day on our phones until our batteries were dead and our storage was near full.

We docked early in the evening and skipped dinner for a few glasses of wine (naughty me) and more kissing. He eventually popped a Viagra and we got to serious business. I had firmly told him earlier that I wanted to be fucked hard enough to be able to take a cock in college, but that it was my first time. That being said he started the experience slow, by rimming me and using a vibrator on my hole to loosen me up. He kept putting lube on me and telling me to relax. I lay back on the towel in the master bedroom and let him work his magic. One moment I would be on my back with my legs spread while he licked and stroked me, the next moment I was stomach down with a toy opening me up. It seemed to go on forever and put me in a state of heaven just by realizing that Todd was getting ready to breed me.

“You ready to fuck, baby?” He finally asked.

I let out a moan I had heard many times in porn and said, “Fill me daddy. I want this so bad.”

“Get on all fours and bend your back, I wanna fuck you doggy style.” He instructed, and I did just that.

With my head down and ass up, he pulled the toy out of me and oozed lube all onto my boy hole before rubbing it with his rock-hard piece and easing the head in. He coached me from tip, to head, to shaft, telling me to breath deep and take it.

“Take it deep you little slut, this is what you want right? If you want my cum you have to take me deep baby. Keep spreading for me that’s it, baby.”

As he kept coaching me through I whimpered and moaned and repeated “oh god, fuck, ow, oh god fuck, fuck” about a thousand times. I was definitely being a bitch about it. But slowly he got his head in and put more lube on, and then pushed deeper. He kept repeating it until he was at least half way in.

“I’m gonna fuck you now baby, don’t take the cock out.” He told me. This was the first command I couldn’t follow that day. Almost immediately after beginning to thrust I started to cry out and tried moving my butt right to remove his cock, but he wasn’t letting go of my hips and he pulled me in closer jamming his cock deep into my virgin boyhole. I jolted forward and his cock slid out of me bouncing and covered in shiny lube. I was pretty embarrassed, but he wasn’t the slightest bit deterred. He turned me onto my back and kissed my while liberally lubing my hole and telling me to guide his cock in.

He was way harder than he was on the boat, and bigger now too. I pointed it into my hole and said “it’s there, put it in daddy.” He started slowly again, this time pushing my legs toward me and spreading them while towering high and dominant over me. I grabbed hold of his arms as he leaned in close and kissed my lips again while inserting himself deeper and deeper. He did it slowly and his cock seemed to never end, until he stopped, took my hips, and held me tight and close.

“It’s all the way in.”

His thrusting started slow and he kept adding lube onto me. At first he just wiggled his hips, but eventually he was moving in and out as if I had a girl pussy. He spent a good minute thrusting hard before I jolted again and he was out. I went to apologize, but he just flipped me over commandingly and started coaching me again.

“Don’t move baby, let me put it in. That a boy. You like it when I fuck you hard? Take that cock you little slut! Are you daddy’s little slut?” he questioned.

I tried to get words out but I was overpowered by moans and whimpers. I won’t lie, it hurt like hell in the best way possible. I felt my ass stretching wide for him past the point of pain and into numbness. That’s when he started going hard. I felt him jamming his manhood deep in my boy pussy, his thick testicles slapping against my tight balls, while hearing his deep moaning and moist sliding of lube as he moved in and out. It was the best sex I have ever had.

At this point I was calling him daddy, begging him to fuck me hard, to make me his slut, and he would slap my ass and tell me how tight I was, or how good of a slut I am. He whipped out his phone at one point to take a video, and I amped up my moaning and got into the moment completely. Everything other than my asshole and Todd’s beautiful cock no longer existed to me and as he hit my spot I couldn’t stop myself from shooting pearly cum onto the towel below me. All my muscles tensed hard and relaxed and the orgasm persisted as he kept hitting a spot inside me. I orgasmed loudly in ecstasy for longer than ever before. The result was a still growing pool of thick cum that rocket shot out of me. I was completely at his mercy now. He controlled my body, my orgasm, and my libido.

But after cumming, I could feel my asshole getting sore again. I knew I couldn’t last long, so my dirty talk changed. I began to beg for his cum. “Seed me daddy. I want your cum so fucking bad.” He fucked me harder but I talked through it. “Oh god, fill me with your cum, I want to feel you inside me dad. Oh fuck.”

I bit the pillow hard and waited while he thrashed my hole and moaned louder.

“Fuck, Carter. I’m gonna cum.”

He pulled out until just his head was inside and with his hand he rubbed his penis. I waited for the moment I anticipated since first falling for him. I waited and nothing happened at first, until he let a loud moan out and moved me back and forth over the top of his cock. He slapped my bubble butt and stayed still panting and letting long breaths out. At first I felt nothing. Then a little wetness inside. Then the sensation came all at once in a wave of moist, sticky warmth that filled me deep and squirted into my hole. He pulled out of me and I basked in the fact that my lover’s cum was finally inside me.

“Don’t move, stay like that baby.” He kept one hand on my ass and pick something up. Then he squeezed my cheek exposing the swollen, used hole in between, and I heard the photo sound on his phone go off a few times as I felt his gooey seed leak from inside me. “Push out the cum for me, baby,” he told me.

I tensed my body and the load popped from inside me and leaked down onto my testicles and around my hole. I heard him take some photos and stroke his cock.

I turned my head to look at him, my ass still in the air, legs shaking and my hole raw. He looked like a god with his heavy breath and his cock still hard from the Viagra.

“Are we done?” I asked.

“Come take a shower. Let’s get you clean and ready to fuck again.”

I told him I would be a minute and I collapsed on the bed, my bum still full of his warm semen trying to find its way out and now leaking onto my cheeks. I just rested a while trying to compose myself. I was overcome with emotion. I felt like crying with joy. I just had my cherry popped by my first love. Todd eventually came into the room wearing a towel and picked me up playfully, taking me into the shower, cleaning me from head to toe, and teaching me how to get his cum out of myself.

That night we rented a porno and Todd asked if I was ready for round two, but I declined because the soreness was too much. We kissed and blew each other for a few hours before bed and we talked about what life would be like now that we were lovers. He said he would tell me when his wife was out and I could come over for some discrete play, but I knew it couldn’t happen. I would leave for college in September and I couldn’t risk letting anyone find out. I fell asleep in his arms that night and we came home from the trip a day early due to bad weather. My ass was sore for days after.

We exchanged accounts on Kik so we could keep chatting while I was away. He sent me some of the videos he took that night and I still have them today. Every now and again he sends me nudes on Kik and tries to get us to meet up, but I never send more than a few pictures in return. We have both moved on to other people. I have had boyfriends and one night stands and threesomes with college jocks, and he divorced his wife and tells me he has a young boyfriend a few towns over. I still go to him for advice and sex tips, but it isn’t the same anymore since I know he still wants to get with me despite this relationship with another college guy.

I made plans to meet with him this past summer for another affair. We had a hotel planned just like my teen fantasy, but he started talking about coming out to my college town so we could spend time together. I asked him why and he told me he loved me. That gave me cold feet and backed out. Over the phone I told him I didn’t regret anything, but I don’t love him. He seemed okay with it, but what he said when I told him I couldn’t come hit me hard.

“You don’t have to love me… but you have to admit that not many people stay this close with the person who has took their cherry.”

Sometimes, I regret not going. He would have loved to see how much I have improved. But I don’t know if the sex would ever be as good. I know he browses reddit from time to time, so in case you see this Todd, you know who you are. Maybe you will find your way back inside me some day and make me feel 18 again <3

Source: reddit.com/r/sexystories/comments/9gsxoq/experience_popping_my_cherry_with_my_dads_friend

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