Training A Fuck Buddy

I was out taking out the trash when I saw that she'd left the dome light in her car. This was a great opportunity because I loved any chance to see Ms. Sheila my neighbor. She was a full figured 50 year old milf if there ever was one - thick legs, chubby tummy and large, soft tits that bounced so nicely when I'd watch her walk and had that long line of cleavage. She wasn't a model - after a divorce, raising kids, she sagged and had wrinkles, but always, always she looked fucking sexy. I'd had a crush on her since we moved in when I was in high school. Her daughters and I had become friends, but it was mostly so I would have the opportunity to sneak peeks at their mom so I could jack off later that night. They'd both left college, which left we with fewer opportunities to see her face to face and I sure as hell was going to take this one!

I walked up to her front door and knocked - I looked down at myself and realized that I wasn't much to look at tonight. My athletic shorts with no boxers, some flip flops and a plain white t-shirt. I had never been good with girls because I was a chubby black guy and all the girls at school thought of 50 cent ripped with a six pack black guy...I was...softer and funny, but no one wanted to take this 5 ft 9 black guy to bed.

She answered the door wearing a robe that was too short and wasn't doing a great job of hiding her sexy figure. She smiled at me "Well hello Jack. How're you?" I could feel my erection coming up as I looked at her - I should have thought about that.

"I'm...ummm...I'm good Ms. Sheila. I just..."

She smiled even brighter and told me to "come in, there was something we need to talk about."

"Yes ma'am." I walked in and brushed her tits - there was no way she didn't notice - she smelled so good. I walked into the dining room that was just past the entrance and had a seat in one of the chairs with the armrests around the table. "What...what can I do for you?"

"Well Jack..." her smile faded and her voice became...stern? "I know about last month when you were in your backyard looking in my open bedroom window..." If I could have, I would've turned beet red - she was talking about when I was out back doing - - I don't even remember --- and I had seen her undressing from her window. I watched the entire incident and had been jacking off to that constantly ever since....and spending more time in the backyard at night. "...and I may have to tell your mother. How do you think she would take that?" I may have been a 20 year old guy, but between paying for community college and paying off a car, i didn't have rnt money and mom would definitely kick me out for a dumbass stunt like this.

"I...I...I'm sorry...please..." I stammered out.

"It didn't help that you came to the door with that erection, Jack...and I also think that you used to spy on me when the girls where here during the year. This makes me very uncomfortable." I started sweating as she sat in a chair across from me with that short cotton robe starting to gap a bit more at the top and riding up her thighs. I couldn't help it - I was about to be ratted out and my cock started getting hard on it's own. And I could smell...something...

"I....I...."

She placed a hand with her long fingernails around my hardening cock without breaking eye contact - "This thing is getting you in a lot of trouble isn't it? Have you ever been fucked Jack?" In any other situation, I would have been surprised to hear her say something like that, but right now I had so many other feelings that I couldn't answer - she squeezed my cock and I moaned out a "No...no..."

"Not even a little blow job or hand job?" She asked - her voice a parody of a teenage girl. I was embarrassed about her seeing me, I was embarrassed about being such a loser and I was afraid of getting in trouble.

"No...well...once..." I could barely hear my own voice. Ms. Sheila still had by my cock in her hand. She squeezed it and said "Tell me about it."

"It was a girl from college who was moving. She told me....she told me she wanted to practice giving a hand job because her boyfriend wanted one...she wanted to do it right..." I was ashamed that the one hand job that I'd gotten was a practice one.

"Well that's just pathetic Jack. Have you jacked off yet today?" She asked.

"No...well...this morning..."

"What were you thinking about?" She was leaning in closer.

"Fucking you." I looked away from her. She grabbed my face with her free hand and brought it back so I was looking at her. She laughed a little.

"You think you could fuck me? I'd have to teach you first. Stay here." She got up, walked into the other room and was back before I could even think about running off. "Put your hands on the arm of the chair." she said from behind me and I did what she said. She then proceeded to tie my arms to the chair with the rope. She did it angrily.

"Jack, if you were a real man, and not a lowly pathetic nigger, you would have fucked me already. But you're not a man yet. You're a scared little boy that needs to learn to fuck and not be afraid of little bitches. I can't believe you even let a bitch like me threaten you, and then let me tie you up. Fucking pathetic." She said all of this as she was pulling my shorts off of me, but left my t-shirt on. I was confused, but I didn't stop her. "At least you've got a fucking nice cock."

All I could mutter was "thanks?" She slapped me hard across the face.

"Until you're more than a nigger boy, you call me Ms. Sheila, do you understand?" I was surprised, and instantly responded "Yes, Ms. Sheila!"

She stood straddling the right wooden arm of the kitchen chair where my hand was tied down. "Take two of your fingers and put them in me...put them in my bitch cunt." I turned my hand over...it was uncomfortable, but I was excited to be fingering the woman who had been the center of my sexual fantasies for years. She untied the robe so that I could see her slit and I pushed my two thick fingers inside of her. I couldn't go up and down so I just kind of wiggled them around. "Niggers..." she muttered "...Never know how to finger a woman...like this" she said making a come here motion in the air with two of her fingers. That smell from earlier was stronger and I realized it was her pussy and that she was getting wetter. She closed her eyes and let me go for awhile explaining how to find her clit and to rub that. She slapped me a few minutes in for being "too gentle...you let a dirty cunt feel like she's in charge and you'll never get any." so I fingered her as roughly as I could tied up. She grabbed my head with one hand and with the other around my throat she began to squeeze and smile for the first time since I walked in "Yes...yes...use those...big...ohhh...nigger...fuck...fingers..." and she screamed "FUCK FUCK FUCK AHHHHHHHHH...." I could barely breathe but I knew from porn that I'd made her cum. My hand was soaked with her juices. She stopped humping my hand back and backed off the chair a bit. She finally let her robe fall to the ground. My already hard cock got harder.

"Ms. Sheila...you're...beautiful." I whispered.

"Don't be a pussy. That's why you're tied to the chair. A man wouldn't be in a position like that." Her beautiful tits swayed as she spoke and her pussy was smooth and she had a sexy tattoo on her tit that I'd often thought about. "Let's teach you how to fuck little boy."

She walked over, turned around and moved another chair in front of her she put her hands on it and guided my cock into her soaking wet and tight pussy. I moaned. "Jack, if you fuck me like a man, I'll suck your big cock. But you've got to treat me like a woman, like a worthless bitch...prove your a man..." she sounded different and I sure as shit wanted head.

I quietly said "Fuck me bitch..." She moaned and said "that's not good enough...you sound like a worthless nigger still..."

I tried grabbing for her hips and barely made contact with my fingers even with her wide, sexy hips. I grabbed her soft skin and pinched or grabbed when I could "Fuck me Sheila....fuck my cock...you...worthless cunt...do your job..." I was angry all of a sudden and bucking my hips into hers hard. She was riding my cock hard but I was pissed that she treated me like this and it made me hornier. She deserved to be fucked like a piece of trash. "I said fuck me like you mean it whore!"

"Oh Jack...more..." And then, against everything I wanted I stopped bucking and scooted the chair back until I was out of her. She turned around angry "What the fuck!?!"

"Listen her you fat ass bitch. Fucking untie me now. Who the fuck do you think you are?" She smile a little bit and untied me.

She bent over the table this time and said "Please fuck me Jack."

I grabbed her hips and pushed into her from behind - all 8 inches of me...I fucked her hard and into the table...she felt all 5 inches of my girth in her fucking cunt "You dirty bitch...you fucking old whore...I'm going to cum in you." I couldn't take much more

"Please cum in me! Give me your nigger cum! Please cum in me...yes...please! Your white whore needs it!" I could feel her getting tight around my cock and I lost it. I grabbed her shoulders and pushed in as deep and as hard as I could and fucked her hard and unloaded load after load of cum in her. I couldn't stop cumming in her tight cunt. When I couldn't cum anymore, I collapsed on top her on the kitchen table...my cock hanging down the crack of her ass, both of us panting.

My face next to hers, she said "Such a big, strong man."

"Bitch...you're talking too much..." I pushed off of her and grabbed her hair and pulled her into the living room. I had never jacked off and been this hard this soon after, so I wanted to take advantage of it when we were there, I sat on the couch and let go of her hair. "Suck it slut" She smiled, and got on her knees and started licking my cock from the very base to the very top. I took off my shirt. She put each of my heavy balls into her mouth and moaned when they were there. She was fingering herself and her long brown hair was on my thighs as she went up and down on my cock. I pushed my cock deeper into her mouth and throat with my hands at the back of her head. The only sound was my occasional grunt or moan and her sucking my hard, black cock.

"How do you taste, you old bitch?" I asked after she'd been on her knees for awhile. Her response was to keep sucking. She ran one of her hands up my thighs and up to my nipple and started tugging on it - it felt fucking amazing. She kept sucking and eventually let go of my nipple "Fucking old cunt...fuck...suck my cock..." was all I could manage to get out.

I could feel my balls get tight and she must have too because she looked up at me, took one of those perfect tits in each hand and wrapped them around my cock and i started fucking her tits "You have such a big cock...please cum for me Jack...please give your white bitch your cum...please cum..."

I looked down at her and grabbed my dick from between her tits and started jerking it hard "You fucking cow...wouldn't your girls be proud of you now?...take...my...FUCKING CUM!!!!" and as I thought about the fact that I was fucking my friends' mom and the way I was talking to her I blew my load in her face and on her tits and in her hair. She was covered in my cum. She put her mouth back on my cock and sucked me until I was soft. She smiled and said "that was so good. What else do you want?"

I grabbed the back of her head and pulled her toward my cock "Suck it until you get me hard again you fucking slut." She put my softening cock in her mouth. In a few minutes I could feel myself getting hard inside of her mouth. I pulled her head back and smacked her on both sides of her face with my cock and grinned wickedly at her. "On your back bitch." She quickly laid down on her back, the cum in her hair drying, her tits held up in her hands. I lifted and spread her legs, and then realized I was going to need leverage for what I wanted to do. I grabbed a couple of pillows off of the couch, lifted her fat ass off the ground and slid the pillows underneath her and then lined my cock up with her still dripping pussy and pushed it in - she grunted "Yes...please Jack...your slut needs your cock in her pussy." I got so turned on hearing her say that, but I just needed to lube my cock up.

I pulled out my cock and pushed two fingers deep into her pussy and pumped a few times, after which quickly pushed them into her ass "Wait...no...stop...I don't..."

"Shut the fuck up and get ready to have your ass fucked, MS Sheila." Her hands came up to my chest as she was trying to pull away but i had grabbed her sexy, wide hips and pulled her close to my cock which was lined up with her asshole. I risked taking one hand away to guide my cock into her tight brown hole when she screamed as it went in.

"FUCK!!! OH FUCK!!! IT'S TOO FUCKING BIG!!!" she had a death grip on my arms as I slowly pushed into her warm, tight ass. She was struggling against me and her asshole was clamped tight. I took one of my hands, placed it on her smoothly shaven pussy put my thumb into her pussy.

I calmly looked down into her eyes, wide with fear and pain. "Sheila. You're going to take my cock in your ass and it will feel good, for me anyway. But...look at me slut...you have to pay for earlier, and you're my bitch now." She relaxed a little. I pushed my head in and she screamed bloody murder, but relaxed after a second. My cock was still rock hard and itching to fuck her tight asshole hard.

After a minute of small thrusts, I pushed more of my cock into her tight, brown asshole.

"Fucking relax and take it Sheila...you feel so good when you fight back...and...I'm..i your ass..." as I slowly picked up speed and force going all the way in until my balls were in the crack of her chubby ass and all the out until just the head was barely in her, she slowly relaxed and went from screaming to occasionally grunting and taking it. "That's right...you're a bitch...fuck...you're my tight bitch...fucking slut...you whore..." I just said it all to her as we looked into each others eyes.

After a few minutes of pushing into her ass I heard her whimper "It's making me need to pee." She looked away. I stopped with my cock in her ass. "Please let me up to go. I won't go anywhere. And I'll bend over so you can fuck my ass easier. Please?"

I smiled and shook my head. "Nothings keeping you from pissing now bitch." I started pushing in and out again. I got even more turned on when she just let her hands down to the side and she started to piss. Not a little. It was as though a hose had been turned on. The thick smell of piss mixed with the smell of sweat, shit and cum. I exploded deep inside her bowls just as she finished pissing. I didn't know my balls could hold so much cum after the previous two events, but I kept cumming and pulled out and finished cumming on her chubby stomach. I could feel my cock soften. I moved from between her legs and laid them on the piss soaked carpet. I stood as she laid there looking up at me...ashamed? Good.

I stood over her naked body, covered in my cum and reeking of her own piss. I grabbed my cock and relaxed as i felt my own stream of urine leave my body and cover her. After I was done I looked back down at her "Well, let's go shower and you'd better make an appointment to get this cleaned tomorrow. That is, if you ever want to be fucked like a bitch ever again." I smiled. She smiled as she got up from the floor and kissed me with her sexy lips. I could taste the traces of cum still on her tongue.

"We need to get my little nigger man cleaned up so he can fuck me again." She put my soft cock in one hand and my balls in another "I want so much more of your giant cock - in anyway you'll let me have it." I smiled. I wasn't going to need to jack off for a long time