Blackmailed, He Had To Fuck My Tits

Author's note: A friend of mine really did this to me. I'm ashamed of it, but turned on by it at the same time. I'm a beginner, so forgive my rookie mistakes. This is my 1st & probably last story, since none of my sexual encounters have been as noteworthy. :( Enjoy!

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My name is Sheryl, and a few years ago I separated from my second Husband for 8 months. His teenage Son moved in with us, and I wasn't used to sharing my hubby. This created a lot of stress between us, and two months later I decided to get an apartment so I could sort myself out. He was upset that I was leaving and he guaranteed I couldn't live on my own because I didn't make enough money. But I was doing it. I moved into a place on the other side of the county, and started over.

Let me describe myself, I was 46 at the time, but my 36 year old Husband always told me I looked younger than the women he saw at his 20 year reunion. I'm of Irish decent, and have brown eyes & lots of cute freckles. My hair's naturally brown, but I've always colored it red. It makes me feel more Irish, and plus it looks good too. I'm 5'5" tall, and my weight is 195 pounds, and I have tanned brown skin. It shows off my freckles. My most outstanding feature are my tits. My first Husband never let me call them boobs. He said old Grandmas have big boobs, what I have are nice big tits. My bra size is 38F. I can squeeze in to a smaller one, but the 38F is more comfortable. At my age, my tits sag some, but Hubby always tell me they have that sexy pear shape that he loves so much. My hips are a little wide too, but it gives me a proportional look that balances out being so top heavy. It's a big hourglass, but a do have a nice hourglass figure.

I met Kenny when I was a member of a company bowling team 4 years ago. Kenny was 48, had a nice build, but middle age was catching up to him. He started losing hair years ago, and was more than a little bald, plus was getting a beer belly. He had a good job, and had hidden a nice stash of cash away from his ex-wife, so he didn't have any worries financially. His divorce was nasty and had gutted him mentally. He was just kind of sad. But he was a good guy and we always had a good time talking. My Husband had met Kenny, and was never threatened by our friendship. He had no problem if Kenny and I went out to dinner occasionally. I didn't find Kenny attractive at all, he was just a lonely guy who needed someone to talk to and bitch about his problems. While we were separated, my Husband and I still had sex. I still loved him, and things were tense between us, but we both had needs even if I was confused about my feelings for him. If anything, it made our sex life better. Even though I lived sex, I would never have sex with him if his Son was in the house (wrong, I know), but once I moved out, it was so hot to quickly and quietly sneak one in while the kid played his Play Station when I visited him. Or he would visit me, and we would have hot sweaty sex in the storage building after he finished some yard work for me. It was like we were dating again. I was a very loyal person, if a bit naïve, so we made promises to each other to stay faithful until we either divorced or reconciled, but our separation was on again, off again. Right now it was very off again, I hadn't spoken to him in a week.

During the weekends I reconnected with friends, and usually had some over to have drinks, play cards or watch movies. They brought the booze and munchies, I provided the place. I was too broke to provide anything else. Living on one income was a lot harder than I thought it would be. One Saturday, Kenny was over along with my friend Lara, and we doing just that, drinking and playing cards. I was laughing at Kenny drunkenly trying to charm his way into Lara pants, but getting shot down all evening. Lara headed home after a few hours of rejecting Kenny, and it was just us. After another hour of tequila shots and chasers we were pretty trashed. He started whining about how he has no luck with women, which got our drunken pity party started. His boss was busting his balls at work, and I thought my marriage was falling apart. I let it slip that my car was going to be repossessed because I couldn't afford rent and a car payment, and God help me, I turned into a crying drunk right there. "How can I get to work with no car? And my Husband, he bought that car as a gift for me, he'll never forgive me if I lose it. What am I going to do?" I sobbed.

Kenny seemed suddenly sober. He stared at me for a long while, I could tell the gears were turning in his head. "I'll pay your car payment." He finally said. I looked up through my tears, what was he talking about?

Kenny said, "Don't worry about it, I'll pay your car payment." I had cleaned his house before for some extra cash, so I jumped up and hugged him and told him I would clean his house, pick up his groceries, even walk his dog for him. I was so relieved; everything was going to be okay.

"I want to fuck your tits." Kenny blurted out. I must have heard him wrong. What did he just say? "Sheryl, I... I'll pay your car payment, but I want to fuck your big tits." I just stared at him, stunned.

"No, no, there is no way." I stammered. "Kenny, I'm married! And you're my friend, why would you say that to me?" I said as I glared at him.

Kenny sighed "Sheryl, your tits are gorgeous. You're a hugger, and every time you hug me you press those puppies into my chest and immediately my dick gets hard. I'm not going home to beat off thinking about cumming in your deep cleavage like I normally do. If you want to keep your car, you're going to have breast sex with me. You won't be cheating, I'll won't touch your pussy, only your tits. Think about it. What will your hubby say when your car is repossessed? You'll never live it down and you know it."

In my alcohol fogged brain, he was actually making sense. I was pissed off at his drunk ass, but he was making sense. There was no way I'd let my Husband know I lost my car, I was too stubborn for that to happen. I really needed the money, but still, it wasn't happening. I made a promise to my Husband. Even if I did break my promise, it would never be with Kenny. There wasn't a thing about him that did it for me sexually. And right now, he made me sick. I told him to get the Hell out.

Kenny started toward the door, stopped and turned back to face me. Looking at the floor he whispered to himself "Shit, fuck it. I'm drunk, and this is gonna happen." He looked up, still unsure of himself, but the tequila made him bold. "Sheryl, I haven't been laid in months. The only physical contact I have with women is when you smash you tits into me when I get a hello hug from you. I've jacked off fantasizing about fucking those tits more times than I can remember. I've even printed our team bowling photo so I can shoot my wad all over your picture. I'm obsessed with you titties and if you don't let me fuck them, I'll tell your Hubby that I fucked you and we're a couple now. Your neighbors see my truck here all the time, it'll be pretty easy to get people to believe it. Sure, I'll probably get my ass kicked, which will hurt for a week. But he'll divorce you for adultery, and everyone will think you're a cheating whore. How long will that hurt? A lot longer than a week. And you'll still lose that car that you love so much. Just a little tit fucking will make that all go away."

I stood there open mouthed. "You wouldn't dare do that to me!"

Kenny took a few steps toward me, "Tonight I would, and I will. I'm already drunk, I'll call him and he'll think the alcohol had the truth just spilling out of me. I. Will. Do. It."

And he would too. I could see it in his bloodshot eyes. Mild mannered Kenny would actually do this. At that point, I was just tired. Tired of crying, tired of worrying about my marriage, and tired of Kenny. I started to justify it to myself. It wasn't cheating if Kenny didn't fuck me, it was just a quick tit fuck. Kenny was drunk and desperate. He had me and we both knew it. But I didn't like being blackmailed, so I was going to go it on my terms. "Ok, I'll do it asshole. But I'm keeping my bra on, you can fuck them, but you don't get to see them." I sneered. Kenny's eyed got wide and he stammered "But you've got to let me see them, I've dreamed so long..." "No! You said you get to fuck them and that's all you'll get. You're a god damn scumbag for making me do this." I barked at him. "But I'd be glad to let you see them instead of fuck them..." I trailed off.

Kenny thought about it for a few seconds and started slowly rubbing his dick through his jeans as he thought about it.

He shook his head and said "No, I definitely want to fuck them, please let me fuck them Sheryl."

"I want a check for $638.00 on my table before I do anything with you." I snapped at him.

Kenny practically ran out to his truck and fetched his check book. His hands were shaking as he frantically wrote out the check. He finished and looked up at me expectantly. I told him to get a towel and sit on the couch. I hadn't unpacked all my personal items yet, so I had no idea where my sex lube was. So I got a bottle of extra virgin (how fitting) olive oil out of the cabinet, did one final shot tequila, and joined him in the living room.

There I got my first look at his dick as he was sitting on the couch jerking it in anticipation. It was long, a little over 6", but it wasn't very thick, like a slightly thicker hot dog wiener. It definitely wasn't the most impressive penis I've ever seen. I sighed and thought, let's get his over with and knelt down in front of him and took my sweater off. Kenny's mouth fell open and he gawked at the tanned mounds of my cleavage pushed up by my white bra. It was a good contrast, tanned tit meat against a bright white bra. He reached out to touch them and I smacked his hand away.

"No touching. It's like a strip club, I can touch you, but you can't touch me, got it?" I growled at him.

Kenny just nodded dumbly as he kept stroking his cock. He may be blackmailing me, but he was still a pussy behind all that booze. I had the tits and the control. "If you touch me, the deals off, understand?" Again, he nodded dumbly. I opened the olive oil and started lubing up tits. Kenny's eyes were wide as he stared into my oily cleavage, and his breathing was ragged. When my well lubed hand disappeared in the valley between my tits, Kenny let out a high pitched grunt and cum shot out of his long skinny dick and landed on the top of my chest. His white load quickly slid down into the oily valley of my cleavage and disappeared in two seconds. If you've even seen cum on an oily body, you'll know what I'm talking about. . I could feel it exit out of the bottom of my bra and slide down my stomach.

Kenny blurted "Oh my fucking God, that was so hot how my load ran down your tits." A huge smile on his face.

As he sat there panting, I shook my head at him in disgust. "Jesus, I didn't even touch you yet. What are you, a bump and squirt teenager?" I snorted as I mocked him. But his dick acted like he was 18, it had barely lost any hardness. And as I stood there wiping his cum off by belly, it started to swell again. I pointed at the door and said "There you go, you came on my tits fulfilling your fantasy, time for you to go." "No, that wasn't the deal!" Kenny shrieked in an unmanly manner as he stood up, his now hard dick throbbing in front of him, "Dammit Sheryl! The deal was a tit fuck. Like you said, you haven't even touched me yet! I'm getting that tit fuck or I start making phone calls."

He quickly sat down as I stomped over to him. He sat there looking up at me with puppy dog eyes, trying to make eye contact, but he couldn't keep his eyes off of my cum covered tits.

"I don't know how a pussy like you found the backbone to do this." I said as I rolled my eyes at him. His passive/aggressive shit was getting old. I thought to myself, "He came that fast without me even touching him, so this tit fuck should go pretty quick."

"Alright prick, just sit there, and don't touch me." I snapped as I knelt down between his legs. I applied some more olive oil to my bra'd up tits, making sure the valley between was nice and slick as Kenny stared intently. I grabbed his hard dick for the first time, getting a long low moan from him. Damn, his cock was so hot in my hands, and hard as a steel rod. Not bad for a balding middle aged man that I hated at the moment. I felt a pang of guilt, this was the first dick other than my Husbands that I had touched in 15 years. I quickly put it out of my mind and put his dick under the bottom of my bra, and slowly leaned forward sliding it into my cleavage until the head of his cock popped out of the top of my tits under my chin. I stopped so Kenny could take it in. I was kneeling in front of him, my oiled tits squeezed together in my bra, with his balls against my belly, and his dick sticking up through my cleavage pointed at my chin.

The look on his face was pure joy and amazement. He started to say something, but I shushed him, and started sliding my tits up and down around his hard cock. As you can imagine, this was not my first experience with breast sex. Having large boobs since I was 14, almost all of my boyfriends wanted to fuck them. After years of experience, I definitely knew what I was doing with my tits. And of course, it's always been a huge turn on to have a hot piece of man meat sliding between my tits. I absolutely loved the feel of hot cum all over my tits. So despite my complete lack of attraction and outright loathing of Kenny right now, I was starting to get wet. The sight of the head of his long prick disappearing and then popping out from between my slick cleavage was just so hot! I felt my nipples swell and could see them sticking out through my bra. I looked up at Kenny, he had an intense look in his eyes as they were glued to the action on my chest. I would slide up to where his dick was the only thing nestled at the bottom of my tits, and then slowly slide down until the head of his dick would poke out between my tits. It was so erotic, my pussy was starting to ache in my soaked panties. I started moving faster. It was like Kenny wasn't there, it was just me and this hard dick. I started to feel dizzy as I got caught up in the moment and started moving faster. I heard myself whispering, "Oh, that feels good, I love that hard dick between my big titties. It's so hot against my chest. Fuck yes. You gonna shoot your big load all over my chest? Gonna cover my big wet tits with your hot cum?"

I was shocked back to reality as I heard a load throaty "uuuuhhhhh" from Kenny. I didn't care as he broke the rules and his hands roughly squeezed my bra and tits together. I just wanted that cum on me, his cum on me, any cum on me. I didn't care at this point! He thrust up hard and almost all of his cock was sticking out the top of my cleavage.

His eyes screwed shut, Kenny loudly grunted "Oh fuck Sheryl! Fuck, fuuuuuuuck!"

His hips were arched off the chair and his purple dick was touching my chin as he shot the wad I craved so much. His load shot off my chin and ran down all over those tits he had dreamed about all those long years. Even though it had only been 20 minutes since he came, it was a huge load. I could feel his dick spasming as he shot his thick ropey gobs of cum all over my chin and chest.

Kenny sank back on couch, spent. He twitched and made whining "ah ah ah" sounds as I slid his super sensitive cock from between my tits. I was torn. My head felt disgusted as I watched him sit there trying to catch his breath. But my pussy was on fire as I looked at my cum covers tits and bra, feeling the wetness of the oil/semen mix slide down my belly, starting to soak the top of my pants. I couldn't remember the last time my pussy had ached for dick this bad.

I made my decision. I leaned over and grabbed Kenny by his shrinking dick. His eyes jerked open and a smile crept over his face. I leaned my cum covered body and face close to his, and again he suddenly had trouble making eyes contact. I felt his dick start to twitch in my hand.

"Was that everything you dreamed it would be?" I purred. He just nodded. "Did that give you a lifetime of jerk off material?" Again, the goofy nod. "Good." I stood up and put my sweater back on over my sloppy chest.

"The deed is done, get the Hell out of my house, now." I told calmly told him. "I think this business transaction has killed our friendship, you black mailing mother fucker."

Now back in the "same old Kenny" mode, he struggled up from the couch and fumbled putting his wilting cock back in his pants. He kept mumbling "Sheryl, I'm sorry, okay. I'm sorry..." as I half walked/half dragged him to the door. He said he'd call me as I locked the door and turned out the light.

After I made sure he left, I locked down the house. I stripped off all of my oily clothes and I sat on my bed, with feelings of guilt. But I was still covered in oil and cum, and my pussy still ached. The smell of the cum was making me throb. My pussy needed to be full. Now. I ransacked the unpacked boxes in the corner of my room looking for my dildos. I found the condoms we used for the occasional anal escapade, but no dildos. I lay back and shoved my fingers in my cunt, but that wasn't doing it. "Fuck!" Frustrated, I looked around for anything that I could fuck myself with. Everything I found was either too big, or too small. I plopped down on at the end my bed and rested my arm on the bedpost. No, I couldn't, not that. I started stroking the bedpost, testing it's size with my hand. It stuck up about 5 inches above the mattress, so it was long enough. It was bigger than any dick I'd ever had, but not by much. The wooden ball at the top would definitely be the hard part. The more I thought about it as I rubbed my pussy, the better it looked. After the night I had, the tequila, the dickhead, the cum bath. I was going to fuck my bedpost.

I slipped the condom over the bedpost. I didn't find the lube, so I coated it with olive oil (hey, it works, try it sometime!) I turned my back to the bed and bent my legs a little until my pussy touched the big wooden head. I positioned it right at the entrance. I slowly let my weight push the bedpost into my honey hole. It was big, God was it big. But with the oil and my drenched pussy, it slid in 2 inches before it got rough. Biting my lip, I eased more of my weight on the wooden ball. The stretching felt good and uncomfortable at the same time. I bounced up and down on the head gently for a few minutes, enjoying the bit of fullness I was getting. I was so hot, something had to give! My gentle bouncing slowly got harder as I closed my eyes, getting caught up in the moment like I did earlier tit fucking that dick. Suddenly...

There was a rush of pain, a quick pop. FUCK! I nearly passed out as the hard wooden ball of the bedpost shot all way into my cunt, slamming into my cervix! I staggered clumsily, grunting like some kind of animal, trying to get all my weight off of the post. I lost my balance, slipped and drove it even deeper. I came like I never had before in my life! Finally! Yes! There was a pleasure and pain tidal wave of sensation that overloaded my brain. I've never before, or since, experienced anything like it. I stood there, connected to my bed in a most obscene manner, panting like a dog, my ears ringing, whispering "oh my fucking god, oh my fucking god" over and over again.

Finally, my tingling pussy got my attention, and I slowly started to lift myself off the post. I expected me to be sore, but damn, it still felt good. I gingerly moved up and down to make sure I was okay, and decided to give myself a proper fuck. I started riding that bedpost like I hadn't had dick in years. I was bouncing up and down, squeezing my big tits, and rubbing all that oily cum all over them. The smell of Kenny's cum, mixing with the scent of my flowing pussy was intoxicating. I could feel my hot pussy juices squirt along the inside of my thighs as the bedpost forced it out of my cunt each time I slammed down on its wooden head.