My Boyfriend's Daddy (Humiliation Cuckolding Erotica) Read online

  My

  Boyfriend’s

  Daddy

  By

  Mary Keeley

  ***

  This is a work of fiction that contains adult situations between consenting adults. All semblances to persons or places, living or dead, are entirely coincidental.

  My boyfriend of three years Dean, his step dad Mr. Warren, and myself were all looking forward to spending the summer together before we all parted ways.

  Dean and I just graduated from high school and were going to different parts of the country to embark on our adult lives at college.

  It’s weird that I want to spend just as much time with Mr. Warren, Dean’s dad, but he has been such a big part of our lives. He was always there to help us out. He was also the laid back parent, the one you could actually could go to with your problems.

  Another thing about Dean’s dad, is that he looks really good for his age. Ever since I laid eyes on him, I’ve had kind of a secret crush on him. He is pretty much like Dean, but just more wise, mature, and even a little funnier. Embarrassing to admit, but his wide manly physique was also more attractive. Also, from what I have been able to tell, um, I don’t know how to say this—he is very hung. On many occasions, I’ve had to pull my eyes away from his midsection before getting caught.

  To kick off the summer, and fully embrace our freedom, Dean and I decided to go to a big music festival eight hours away in Chicago. We bought the tickets months ago in anticipation of seeing our favorite bands, having a few nights away from our boring old hometown, and visiting a big city we had never been too.

  Then it turns out that some old school band that Dean’s Dad loved when he was a kid was headlining the festival. So, it was only natural to let him come along. Like I said, he is so chill that you don’t have to worry about him judging you. Hell, he was the first person to buy us alcohol and the first pot we smoked came from his dresser.

  While waiting, with graduation and all, the time flew by and it was finally the night before. We all enthusiastically packed our bags. Dean and I furiously texted each other back and forth about how excited we were.

  We set out on a Friday morning. We were going to spend three nights listening to music, getting high, sleeping in a tent, and basically just unabashedly taking in life. And do this we did.

  It was so hot, I was wearing a bikini top the whole weekend surrounded by thousands of people. I danced half naked for hours in a sea of people enjoying every second. The music was good, and so loud, that I probably won’t be able to hear until fall. Dean and I slept in the same sleeping bag every night, slowly and quietly fucking ourselves to sleep next to his dad. Luckily, Mr. Warren did not seem to notice, or if he did, he did not really mind it.

  All good things come to an end, and after the headliner of the last night we had to say so long to the good times.

  Or did we?

  Mr. Warren had to work the Monday after the festival, absolutely no way around it, so we had to come home that night despite how tired we all were. Dean and I were okay with that, because, we both really wanted him to go and this was the exception we had to make. So, Dean and I made the pledge to drive the eight hours home while he slept for work.

  We all had a great time and we’re kind of delirious from the all the heat and dancing earlier that day. However, we stuck to our plan and piled into the car with our game plan for staying awake in mind. Dean had his “driving music,” and several cans of an energy drink called Electrocute ready to go, and I had a book light and my crossword puzzles. Unfortunately, I promised to keep Dean awake, so I have to stay alert and make sure we all get home safe and sound.

  Even after the first can of Electrocute, about a half hour away from the festival grounds, Dean was looking very sleepy while Dean’s Dad and I were still running on post festival adrenaline. I was yelling out my cross word questions over Dean’s blaring music and Mr. Warren racked his brain to help.

  I was getting so into figuring them out, that while sitting in the center of the back seat, I pulled my legs up to my chest, so I could better scribble in the answers that Mr. Warren and I were coming up with. After fifteen minutes, I looked up and caught Dean’s dad glancing at my private mound obscured beneath the stretched fabric of my tiny panties as I excitedly rocked back and forth. When he stopped looking, I took the chance to reach down adjusting the elastic just to make sure I was all covered.

  All in all, this probably had something to with why he was so enthusiastic about helping. Dean didn’t seem to mind or notice, and lacking sleep and apparently judgment neither did I.

  An hour later, Dean is totally nodding out while doing everything he can to stay awake. One minute he’s talking a mile a minute, turning the music up and down, opening and closing his window, chugging an energy drink, and telling us to tell him stories.

  His judgment, clouded by a lack sleep, becomes askew as he steers the conversation in inappropriate directions. He wants to hear all the bad stuff, like when we first masturbated, when we lost our virginity, and who we thought was really hot at the festival.

  Then like a flash of lightening, he asks if I remember that night we drove back from his cousin’s house and tells his Dad, “that it is a pretty good story.”

  “Of course I do. You don’t want me to tell THAT story do you?”

  “We are all so tired we will not even remember tomorrow,” Dean encourages me.

  “I don’t know . . . in front of your Dad?”

  “Okay, now I’m interested,” Dean’s Dad chimes in.

  “It will make me stay awake, so we won’t crash and die.”

  Just the mention of it seems to perk him up, so I go ahead and tell the story.

  “This trip home kind of me reminds of the time Dean and I went to visit his cousin, your nephew, when they lived a few hours away. We left late at night and he was so tired, but we decided to drive home because my parents told us we had to be back before midnight. Do you want me to go on?”

  “Yeah, yeah . . . you have to,” Dean pleads.

  “Anyways, as soon as Dean started to dose off, I reached inside of his pants and pulled out his you know what. I kept him right on the verge . . . of . . . uh . . . coming for nearly two hours. I would stop right when he told me to, so that he could keep the blood rushing making him wide awake. He told me it was better than a whole cooler of energy drinks from the gas station.”

  “Fuck yeah. Too bad they can’t bottle that feeling—that person would be a millionaire,” Dean confirms my accuracy.

  I chuckle at Dean’s joke and glance around at the guys in the front seat who were probably wishing that story was a lot longer, or a little more in depth at least. I pay special attention to Dean’s dad’s reaction.

  Applied to the present scenario, with Mr. Warren in tow, a repeat of this story seemed pretty unlikely.

  However, following the story, after a couple of minutes of silence, Dean tells me he has an idea.

  “Okay. Here’s the deal guys, I’m going to come clean. Having been around so many people this weekend, I’m horny as fuck from watching Mary walk around in that tiny skirt and bikini top in public. I’ve had a thousand unrequited boners this weekend. Just to get me through the night, and give something to look forward too, you have to show me something Mary. I’ll take anything,” Dean pleads.

  “Dad has to look away,” I say feigning modesty. I’ve known that both of them, among others, have been stealing glances at me all weekend.

  “Shucks,” Dean’s dad says to himself glancing at Dean to see his reaction.

  “Just make sense. We don’t want daddy sitting on a stiffy the whole way hom
e, the old boy needs his rest,” Dean assuredly says.

  “Dean, the voice of reason, but seriously you know I think she’s fucking beautiful,” Dean’s dad says testing the boundaries of the trios’ familiar bond.

  “You don’t have to tell me,” Dean says glancing back ready to catch a glimpse of my body. “You got more than an eyeful this weekend for sure.”

  During this exchange, I sit in the back seat with my cheeks turning bright red, feeling like I’m literally melting from embarrassment. To think that a man of Mr. Warren’s knowledge and handsomeness finds me beautiful, not even just cute, is good news.

  Dean’s dad reluctantly leans his head to the side and places his hand haphazardly over top of his eyes.

  Dean’s rapt attention fluctuates between the backseat and the highway, that he is sharing with just a few semi trucks.

  I lean back building suspense. Spreading my legs, I let my short skirt fall around my hips revealing my pink thong that hugs my young pussy before cascading into in a thin line that reveals my round ass pushed against the fabric of the seat. I make eye contact with Dean in the mirror, letting him know to keep his eyes on me. When I do this, he reaches down and charts the course of his erection. I reach a hand down my shirt. I grasps my more than a handful C cup and lift upwards while I pull my top down with the other hand. I massage my breast upward, ending by pulling my pink nipple. Closing my eyes, I do this a few more times and resist the urge to reach my hand down my panties and rub my dampening slit.

  This is the first time I’ve ever had my breast out in a public place, and it’s really a thrill. I would love to take my exposure a little further and let some of the weary passerby’s glimpse my young body.

  “Fuuuccckkk,” Dean’s dad says, unable to resist, turning around and glancing at my exposed tit. “I’m so sorry. I thought it was over.”

  “Dad, you are such a cheater. I would have told when the coast was clear.”

  “Ah, I have to admit I’ve thought about seeing Mary’s breast more than once . . .okay . . . well every time she bent over this weekend I was looking down her top just waiting to see what I’m seeing right now, but hell, my imagination did not do them justice,” Dean’s dad admits.

  I don’t know why I don’t cover myself up. I guess I really like having Dean’s Dad staring at my chest. It feels so wrong because I have his full attention, while Dean can only steal glimpses.

  “Dude, you’re not even supposed to be looking. Those are fucking mine,” Dean lightheartedly snaps.

  With both of these guys looking, I can feel my whole body flushing and overwhelmed.

  Something comes over me forcing me to take things a little further. I reach my hand down my panties and start rubbing my moistening lips underneath the thin cotton.

  Both men are enraptured. Dean’s dad turns almost completely around in his seat and Dean is trying to drive while taking in the back seat sights. With both of them looking at me, doing what I have only done in private a few times is a complete turn on.

  Finally, I feel a little embarrassed, I pull my hand up and decide that we have a long way to go and I need to pace myself. However, I do decide keep my long term boyfriend and his dad wide awake, so, I go ahead and undo the latch of my swimsuit top holding in my beautiful natural breast. I pull my top off exposing the mesmerizing heft of my chest.

  Torturing them both, again pulling my knees up to my chest, but not covering my breast I go back to crossword puzzles topless in the back seat.

  “I’m fucking wide awake now for sure,” Dean says.

  “Err, I second that,” Mr. Warren adds.

  Dean, trying to remain part of the temporarily interrupted show, turns on the overhead lights of the car letting the light shimmer across my white skin that shimmers with a golden hue from the weekend spent in the sun.

  Completely gushing at the thought of having my eighteen year old breast viewable to anyone that drives by, I pull at my tight panties that are glued to my wet pussy. Sitting in a mess of my inner warmth, I know before long something is going to have to be done about this.

  A couple hours into the drive, we are still cloaked in darkness of the middle of the night. Dean’s dad and I are still wide awake, pretending to be occupied, while we steal glances at each other.

  Ever since Dean’s dare, when my top came off, his Dad has been rock hard. I’m absolutely mesmerized by the hugeness of the outline of his dick uncomfortably shoved half way down his thigh. He might be older, but no need for Viagra I guess.

  Dean and I have a lot of sex and I really enjoy it, but it has been three years and has become pretty standard at this point. This makes sitting topless in the back of his car, while being eye fucked by his father, who looks to be packing a 16 ounce beer can in his jeans, exactly what I need. The cool night air feels electrified like never before.

  Dean is oblivious to the visual foreplay taking place between me and his dad. Dean has slipped into the monotonous drive, looking straight ahead with tired determination.

  I take advantage of his singular focus and put one leg down and aim the darkening fabric of my panties in his dad’s direction. Mr. Warren takes notice, glancing back at me trying not to draw Dean’s attention. I then use one hand to go back to rubbing my breasts, pushing them upward while squeezing my nipples all the while imagining Mr. Warren’s rough grip and his suckling mouth all over me while Dean watches. Almost subconsciously, I slip my other hand down my panties and start to massage my clit in a circular motion. With every fifth round, I plunge my middle finger downward and pull my wetness upward.

  Mr. Warren’s eyes keep darting between my masturbating hand, my young breast, and Dean’s eyes. Dean’s dad is becoming more and more agitated, pushing and pulling at the monster in between his legs.

  Mr. Warren assuredly realizes he is never going to sleep, when the only thing he can think about is shoving his dick in his son’s girlfriend while zooming down the highway at 80 miles per hour. Getting brave, Mr. Warren unfastens his pants button and slowly unzips his jeans. Mr. Warren has obviously made up his mind about what to do.

  As though not to startle a wild animal he slowly reaches in his jeans pulls his mammoth dick out of his jeans. My brain is screaming, “shit, shit, shit, shit . . . .is this really happening.” I feel like I’m trapped in some insane fever dream.

  Momentarily Mr. Warren leans his head back and gently tugs himself to a very large full erection. At this point, my gaze is fixed and my brain short circuits with a combination of excitement and fear. Despite this, my hands still feverishly work my soft breast and wet pussy—I’ve even pulled my panties off to the side to reveal the slick mounds of my labia. With one hand steadying the base of his cock, and the other slowly ascending up and down its length, Mr. Warren turns around to take in the real live porno happening on the highway under the umbrella of night.

  Unable to control the desire to feel such a mammoth cock in my tiny hands, I say Dean be damned. Reaching forward I replace Mr. Warren’s hand at the bottom of his cock with mine. I lean in and take a closer look and every bit of the thick eight and a half inches is enticing.

  My leaning forward must have interrupted Dean’s driving stupor, as he slowly turn his head to take in what has just started beside him between his girlfriend and dad.

  Who knows? Maybe this will really keep him awake.

  “What the fuck guys?” He says with just a hint of rage.

  “It’s Mary’s fault son. Her tits are hands down the most perfect I have I ever seen,” Mr. Warren says while brazenly reaching towards my chest and grabbing my breasts. “And whenever I would start even thinking about sleep, this thing would start twitching,” Mr. Warren says looking down at his cock now being slowly pulled from the base to the head by my hand.

  “Dad, that’s not fucking cool,” Dean says while gradually kind of glazing over watching my hand stroke his dad’s mammoth cock. “Your dick is a fucking cannon . . . Jesus Christ . . . man, it’s bigger than Mary’s forearm,” Dean says gla
ncing between the yellow line, Mr. Warren’s hard dick (now being measured against my arm), and me as I’m unknowingly licking my lips. “Mary, there is no way you could take that in any hole you have. Sorry about your luck Dad—you might as well put that back in your pants,” Dean says nervously, as though he has unwittingly just offered us a challenge.

  I’m turned on enough right now to take this bet.

  “Oh yeah,” I say leaning in for a very close look. I glance up at Dean, who is adjusting his growing cock. With my face this close, I realize his dick is a big as my entire head. I start small, holding his dick steady with my hand while I start licking from the base of his cock upwards. Then eager to jump right in, I put his swollen cock head into my mouth, feeling it’s about as far I can go, while rhythmically tugging upward with my hand. Occasionally, gagging each time, between my rhythmic sucking I’ll test the limits of my mouth by shoving his length down my throat as far I can. Trying to help, Dean’s dad has unbuckled his seat belt so he can better thrust into my face. Mr. Warren is now slightly moaning with his eyes shut only opening them off and on to check my progress and glimpse my round breast pushing against his thigh.

  Feeling slightly bad for Dean, as the slurping sounds coming from his dad’s cock going into his girlfriend’s mouth become more and more pronounced. I decide to take sucking breaks, in which I just pull at Mr. Warren’s length while making lascivious eye contact with Dean as if to say, “I’m doing this for you.” Even though, as I grind my wet pussy against the center console, I assuredly believe that I would follow Mr. Warren’s hardon anywhere in the world.

  “Well fuck,” Dead says turning bright red with embarrassment, but unable to stay out of the action any longer. Dean unzips his pants while turning on the cruise control. Catching his action out of the corner of my eye, I use my free hand to assist him in pulling out his comparatively average stiff dick. I continue to slobber, gasp, and gag on Mr. Warren’s enormous rod while I begin stroking Dean’s erection.