Jamie the Masochistic Cuckoldress

Jamie, a woman somewhat frumpy shoulder length brown hair, warm brown eyes. A mother, and wife whom I got to know over several months. I was just getting out of a bad marriage, and she was having issues in hers. So we commiserated me and my divorce, her and her job's unbelievable emotional stresses. Truthfully aside from her cute smile, I'm not sure I'd have noticed her at first. I'd run into her at the office, helped her with a few things. Then just saw her around, we ended up chatting about my divorce, and her issues.

My divorce was a nightmare as my ex had a lot of mental issues, and things she put me and my children through. Jamie helped talk me through some of it, and not lashing out at my ex. That and reminding me to keep my cool and handle things carefully and with restraint. It was unbelievably helpful to me, the amount of comfort and concern as I went through things.

Jamie meanwhile dealt with her own daemons. Her marriage was a bit of a mess, her husband wasn't paying attention to her. Or helping her with her emotional or sexual needs. He routinely recognized their was a problem then would walk off to get drunk with his friends. She dealt with a lot of emotional pain daily from her job, seeing bad things happen to people and helping them where she could. She has a big heart. But with that comes her need for a stress relief.

Jamie is the mom next door, not necessarily the milf. She had her simple features, but really she came off as soccer mom. Shoulder length brown hair, 36B-34-38 maybe 5ft 4in a bit pudgy, but not fat. Light freckles covered her oval face, sparsely on her neck, then seemed to become more pronounced on her shoulders, and back all the way down her ass.

I saw it in her, the desire to redirect the emotional pain she sucked in, and let it out through her own pain and suffering. I brought it up jokingly, that she needed to ask her husband for a spanking to help her get the relief she needed. She laughed along, and said it's happened a few times.. But her husband always avoided it, and any of her real needs. She slowly let out that she had a deep desire for punishment ideally it would have been via her husband. She'd been married for several years, with two kids. And really, he saw sex to be used for procreation, and little else. He saw her desire to be tied up, spanked, choked, and treated roughly as both disgusting and out of the question. He rarely attempted to even appease her needs, the closest he came was when she begged him to use her ass. In the end of it she told me several days later, was barely satisfying as his cock was both small, thin, and he was barely rough enough. The only silver lining was the pain, control, and humiliation she got from him taking her ass with almost no lube.

Her and I kept texting... sometimes verging onto sexting... several times we'd end up talking about some of her fantasies. To be used, be a slave, be punished, relieved of her daily stresses ideally by her husband. Metal cuffs wrists to ankles to collar, naked waiting for her husband, waiting on his every whim. Punished severely for anything out of place, or for a slow response. At night when she'd messed up, have her wear 5" high heels (anything over 3" was never easy for her) a rope around her neck holding her to the wall. A vibe pressed deep inside running high, her cunt duct taped closed, gagged. A combination of dread and excitement of when the tape will get removed with a lot of her cunt hair. Unless she's lucky and the glue on the tape wears off...

Not the most realistic with two kids running around.

Any case our conversations kept getting more interesting... we'd talk about different ways she punished herself sometimes. I'd suggest other ways to punish her tits, spank her own ass. Even a few times taking her hair brush and after masturbating with it, ending only after roughly taking her own ass with it.

After a few months of sexting and teasing intermittently, she ended up having a major blow up with her husband. From what she told me they'd started to have sex, she was on top.. Which was a common occurrence, as he wanted to put as minimal effort in as possible it seemed. While riding him, she grabbed the clamps and put them on her nipples.. She started gushing out of her cunt when she'd put them on, squeezing hard on his cock... They fucked for half a minute or he came really quickly... and proceeded to push her off of him. She started begging him to pull and tug her tits and fuck her till she came. At which point he seemed disgusted by the whole situation, leaving her on the bed. She ended up grabbing her dildo and masturbating on the bed as he walked off grabbed a beer and watched a game.

I recall walking with her to grab a coffee, she'd mentioned earlier in the day that she'd been super stressed and needed to submit. She had two phone meetings later on, and a staff meeting so she couldn't leave for the day. She was a bit nervous and was like I have a fantasy.

"My master would meet me out for lunch, he'd find a safe place. He'd bind my tits, then put heavy clamps on both my nipples. Tease me, then make me go back to work. Forced to walk around with my tits about to spill out of my top. And my hard nipples captured and torturing me till I made it through the day. He'd text me in between meetings and tell me to twist them, give me breaks with the clamps and then have me put them back on."

So I asked if she had those clamps with her, "yeah" she meekly said.

She pulled them from her purse, and put them in my hand.

"Well I can see what I can come up with."

The Starbucks had a family bathroom, as she walked by it. I opened the door and pulled her in, locking the door. I pressed her against the wall..

"Do you want this."

"oh fuck... yes"

Throwing my backpack on the floor, I looked her over. She'd been purposely showing herself off to me. Her knee length skirt she'd pulled up, halfway up her thighs before she'd left her desk. She'd flashed her tits at me several times, dropping her bag at one point and making sure I could look down her loose top.

Her tongue was down my throat in seconds.

She'd worn a white button down top with a deep V sweater, with three of the top buttons undone. I pulled the sweater up to her neck, as I undid the rest of her buttons as I roughly groped her tits. I then removed her bra. Her nipples hard in my hands as I groped them.

"We don't have much time."

I leaned down taking each nipple in my mouth sucking it hard, and then biting it. I slowly released them by grinding them through my teeth. All she could say was oh shit, I'd let me hand wander under her skirt. Pushing her damp panties to the side, and probing her sloppy cunt. She went up on her toes as I roughly bit her nipples, and probed her roughly.

I quickly turned her to face the cold tile wall, telling her to put her hands behind her back. I pressed on her neck forcing her tits against the cold tiles. I pulled the back of her skirt up, and had her hold it up, I pulled her panties down showing her ass off.

"Stay"

Being a bit of a geek and running around with my own stuff for work I had my tech bag with me. She didn't have large breasts, but they were still a large handful. I dug through my bag, finding both zip ties, and a bunch of rubber bands. Her tits weren't that large, and I had several 1/4" wide rubber bands. Zip ties would be harder for her to take off later, or if she had a problem.

I kept a zip tie or two out, and turned her back around. I showed her the two options her eyes bulged a bit at the two options.

"Today you get the rubber bands. The zip ties are for next time maybe it'd be fun to be forced to have your husband cut them off you.", throwing the ties in my bag. (She knew I wouldn't but the idea of it unless it was something we agreed on, but I could tell really got her off.)

I put two rubber bands on my hand, then pulled her left nipple up high stretching it. She went on her toes, gripping her hands behind herself.

"shit..shit..shit......."

"keep quiet.. people are right outside.."

I slid both rubber bands over my hand and down to the base of her left tit. It didn't seem to cinch her tit much at first, so I doubled each rubber band over. Stretching them again over her tit. That did it.

I then repeated on her right tit. She was biting her lip, closed her eyes reveling in the feeling. I then whispered in her ear "are you ready?"

unsure of what I was doing, but keeping her eyes closed I kissed her on her lips. Letting my tongue massage hers, keeping her occupied. I pulled the first clamp from my pocket, opening it wide. I quickly moved it over her left nipple, pressed deep and let go. Her eyes shot open and yelled, as I held her head to me kissing. Her body convulsed and spasmed a little, not letting her go. Holding her tight, her eyes still wide, as she calmed down. I pulled the other clamp from my pocket, this time letting her see it.

Breaking our kiss for a moment, "do you want it."

She closed her eyes, and nodded.

I kissed her, and gently rubbed the edge of the binder clamp on her thick nipple, slowly pressing it in, and gently letting it close on her other nipple.

Looking her in the eyes, I gently toyed with the two clamps. Her nipples turning an angry red from their punishment. I then used the metal loop and pulled it up into the air, exposing the underside of her tit. I bit the underside and sucked as hard as I could for almost two minutes. Then I did the other tit. Leaving her small bite marks on each tit.

I could tell she expected me to release her nipples at least. I just took her bra, threw it in my bag. Buttoned up several of the buttons, and pulled her sweater back down. The rubber bands made her tits swell more out of opening in her top. I'd left another button or two open. And the two metal binder clamps, I could tell stretched her uncomfortably from being pulled down. But under the shirt and sweater it looked like she had nipple piercings poking her shirt.

"ready to go?"

She blinked for a second.

"I can't go out there like this"

I turned her around, flipped up her skirt and gave her 10 hard quick spanks. She held her breath, holding it in. Leaving her ass a warm red.

"are you ready now?" turning her quickly back around.

"Yes sir" (we'd talked about it in the past, and master just wasn't for me)

She was blushing, as we got our coffee. I purposely was slow, enjoying her looking around nervously. A goth college girl, walked by wearing a short dress with a bunch of piercings. She'd been staring at Jamie the whole time. I swear I heard her say she wished that milf had been in the bathroom for her to molest, as she thought she'd be up for it to her friend.

Jamie just blushed even more.

"Oh god, I came when you clamped them. But I can't go into the office like this, and my nipples will fall off before the end of the day."

"You'll be fine, when you get back hit the bathroom and take off the clamps. But the rubber bands stay on till you get home. And text me around 4pm, after your meetings."

As she walked away, I swatted her ass.

At 4, I had her slide one rubber band halfway down each tit. Then pull back and let go the rubber band, several times on each tit. She let me know she had a red line now on the underside of each tit. When she got home at 5:30, she texted me that she was removing the rubber bands. And how they were so sensitive. I found out later, she'd fucked her husband as soon as he walked in the door. Telling the kids they needed a few minutes and sent them out to play with some friends.

When I saw her the next day, she told me she had a plug in her ass. She'd been able to get him to fuck her ass in the am, and she plugged it right after. And she'd been rubbing the bruises all day on her tits, which made her cunt and ass clench. I asked if her hubby had commented about the bruises.. Oh him, she just said she bumped into something. He knows she can be clumsy.

We continued to chat, then she brought up how her husband watches porn sometimes. And he thinks he sees her in different porn movies, or pictures. Yes she's a bit of a milf, but definitely would be on the amateur end of things if she ever had. I did ask, if they'd ever talked about a 3-some or her playing around. I mean her and I had done several things, but I'd never fucked her or gotten a bj to this point. More just told her to do things, or my rough handling/groping, and a some kissing.

Most of the movies he was jacking off to were ones where the lady was cheating, with guys with huge cocks. And several with ladies taking the girl who looked similar to his wife. For Jamie the one thing she got out of this when he did this. Was she got to crawl under the table, and give him a bj while he watched vids. He just asked for a bj, she loved forcing her throat down his cock. It being what it was, it wasn't much of a challenge. It at least reached the back of her throat and hit her uvula.

So we kept chatting, different parts were getting more serious... I laid it out plain and simple. That no offense, I was just separated a few months before hand. She needed to figure out for herself whether she was going to split with her husband or not. But either way don't count me as her boyfriend, this was and is just us playing and relieving each others steam. Basically, a fwb situation and that was it.

Any case we kept talking about things...

Several times I'd had her remove her panties at work, or even at home. Use rubber bands to punish her own tits. She had a thin short vibrator she used a few times on both her cunt and ass. Jamie also had a small plug, which sent her into a very submissive mood. But she wasn't used to wearing it for long periods.

So then on a Monday a few weeks later she told me her husband was going out of state on a fishing trip with some friends. Her kids were going to their friends, and she'd be free all of Saturday.

"Sir, I want you to take me. Punish me, fuck me, use me like a whore. I don't want to cum, or I should say I don't want to have permission to cum."

"You do know that I'm fairly thick and long, and most ladies cum several times." I'm a bit of a bull. I enjoy having a woman spasming under me, which is what usually happens. Whether it's with my cock, or when I go down on them.

"But no cumming, we'll need to come up with a punishment if you do though. And you may want to stretch that ass, as I will be using it. And bring your anal plug."

Friday came, she pulled up. She was wearing black fuck boots ending just before her knees. A mini skirt, and a loose button up white shirt. Aside from some makeup and her earrings.

I invited her in, then pressed her against the wall roughly. And kissed her hard, as she pressed against me and felt my long thick cock through my pants. I put my hand against her throat, looking deep in her eyes.

"Are you sure you want to do this?"

"Yes"

"So your going to cheat on your husband? ... Go back home, climb into your marital bed with my cum up your cunt and ass?"

"Oh fuck..."

"Listen, we go any further and you need to realize what you are doing. We can stop at any time."

"I want it. I want you."

I let my other hand wander down grabbing her tits roughly as she moaned. I worked my hand down, groping her pussy. As she squirmed against the wall, as I held her by her throat.

"Spread those legs!"

As she spread them I swatted her inner thighs, making her open wider. I let my fingers work their way up her thigh. Reaching her crotch I encountered her panties, pushing them aside, I slid my finger inside of Jamie. She groaned, as I probed her soaking wet cunt deeply..

"So two things slut. First your wearing panties, secondly your cunt looks like a forest"

Taking her by the neck, I quickly lean her over the dining room table. She put her hands behind her back. I reached under her skirt and pulled her panties off, slipping them into my pocket.

Standing behind her, she was grinding her ass against me. I put my hand on her lower back, stepping to the side. I gave her a few spanks on each ass cheek, leaving them both a light pink.

Pulling her against me by her hair, I used my other hand to continue groping her all over.

"Upstairs down the hall, is my bedroom. Strip, and masturbate on the bed, no cumming, and leave the door wide open."

Her eyes went wide with that.. she'd mentioned several fantasies of being watched. She'd also mentioned that anytime she'd ever done anything sexual she locked her door, even with her husband.

I took my time downstairs, got two glasses of ice water. Spent a minute or two checking on things, and made sure the door was locked. I didn't need my ex or anyone else just walking in, or if her husband was tracking her phone. I doubted it, but didn't mean I needed an issue at my house.

I stood at the door, she'd stripped but had kept her fuck boots on. She was moaning, one hand grabbing and twisting her nipples as hard as she could. The other rubbing her clit, with a finger probing her cunt roughly.

Seeing me, she stopped.

"Jamie, we talked about filming this, would you like to?"

"Really? Yes definitely...."

"Cunt did I tell you to stop masturbating?"

"No sir"

She continued masturbating, as I walked through the room setting the glasses down.

I grabbed the camcorder and stand I'd prepped earlier in the day in case she really did want to record it. Popping it off the stand, I turned it on. And got it recording, recording her face, and down her body. As she roughly pulled and pinched her nipples. Down to her hairy cunt, then put it back on the stand making sure her cunt and face would get recorded.

Her eyes a bit wide at the idea, loving every second of the attention. We'd talked several times about how in most of her fantasies she was essentially used in public, or caught. And the idea of others watching the video later and masturbating to it, really got her going.

I went to my bathroom, got my electric razor and other shaving supplies.

Setting them on the edge of the bed.

I went to my nightstand drawer, and pulled out a set of clover nipple clamps attached via a long chain, a blindfold, as well as a bullet vibrator.

"May I cum sir."

"No"

Pushing her hand away from her crotch, I slid the vibrator in, setting it on low.

"Slut, what were you to do before you came here?"

"I was to prepare myself for you."

"And what does that mean?"

"I was to prepare my holes, I was to trim my cunt, and clean my filthy ass to make it presentable. I was to then dress as sexy as I could for you."

"So since it's obvious you didn't trim your cunt, did you clean your ass out?"

"I did once this morning, I should have twice but I didn't have time. And I forgot about my cunt."

"Well those are two things we can fix. Grab your ankles and keep them by your head."

"yes sir"

I took both nipples playing with them roughly, and pulled on them hard. Pulling her slightly off the bed.. arrgghh.... I took the chain wrapped it around her pony tail, tilting her head to look at her crotch, holding it there, I took the one clover clamp and released it behind her nipple.

Agghhhh.. Fuck..

I proceeded to grab the other clamp, and released it over her other nipple.

Fuck...fuck... through gritted teeth...

"Would you like me to re-apply them?"

"no..sorry sir"

"I think a milf like you would have a better behaved mouth.. Why don't you just nod or shake your head instead.."

I shook her head for her, which caused her nipples to be tugged roughly..

"Thank you sir."

I released her head, that I'd been holding up..

aArggggg...

She then did her best to keep her head up, looking down at her crotch.

"Good, now I think I can get this mess dealt with. Oh and since you didn't take care of it, I'm shaving it all off. I'm sure your husband will notice."