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Friend with Painful Benefits

Story of weekly sm romps with an older women I became friends with.
I met Sheryl about 10 years ago, when she married my older cousin Dan. I was impressed, because she was very attractive and seemed very together. It was surprising, because while Dan was a fine looking guy, he was pretty much a loser.

This was her 2nd marriage. Sheryl was in her late 30's, had a pretty face and long dark blonde hair. The day I met her, she was wearing a red tank top which showed off her fit arms and shoulders. She wore tight black cotton pants which showed off her nice tight ass. Not bad I thought. 

I did not see her again for 8 years. Around that time, I had just started my own construction and trucking company. Dan who had been very experienced in both, called to see if I would hire him. I agreed I could use the help and he joined me. Sheryl stopped by work one day to drop off something for Dan. She came and we talked about how long it had been since we met and how time flies. She had aged a just a little bit, and had gained a few pounds. Overall very good for a women in her mid 40's. As she turned to leave, I checked out her ass. Even with a few extra pounds her ass looked great still. She was wearing tight white shorts and I could see a floral print thong under them. Not bad at all I was thinking.

It turned out that Jessica, a girl who I hired to work my front desk, had known Sheryl from a previous job.

"Oh my god, I can't believe that is Dan's wife!" she said.

I asked what the big deal was.

"I used to work with her at the mall," Jessica said.

"So why can't you believe that's Dan's wife?" I asked.

"Nothing, I just know some things, that's all," Jessica replied.

Jessica did not want to tell me anything, but I would not let up until she did. Jessica told me that at a work party, Sheryl had gotten drunk and dished out details of her sex life. Sheryl had told Jessica she was a nympho and wanted sex several times a day. Sheryl told Jessica she liked it every which way including in the ass. Sheryl also told her about loving to dominate, and how she got off on spanking and whipping her man.

She told Jessica that she was bummed out because her first husband was into and she could quote "Whip the shit out of him as hard as I wanted". Sheryl complained that Dan was a total "pussy" about it and that he told her to stop, even if she wasn't hitting him very hard. Sheryl admitted to Jessica that she had gotten together with her ex-husband just to whip him and spank him. Sheryl said they never had sex at these meetings, just whippings and spankings. Sheryl told Jessica she had a trunk in her closet where she kept whips, straps, paddles, and restraints.

Fast forward 1 1/2 years. One day without notice, Dan hit the road. Quit his job with me and left Sheryl a Dear John and divorce papers. Sheryl called one day. She was not to broken up about things, but asked if I might be able to help out. She needed some things moved into storage. I told her no problem and I could help her.

The next Saturday morning I was on my way to her house. I was thinking about all the stuff Jessica had told me. I had fantasized about Sheryl a little bit in the time after Jessica told me everything. I imagined how she would look using a whip or giving a spanking. I didn't know how, but I knew I had to find someway to let Sheryl know I was into whipping and spanking. I was a little shy about it, but I had a golden opportunity.

I arrived at her house about 10 am. She answered the door looking sleepy and still in her pajamas. "Sorry, I just got up," she said.

I went in the door and followed her to her kitchen. She was wearing black silky pajama shorts and a matching tank top. The pajama shorts were bunched up her ass crack so when she walked I got a nice view of her round ass cheeks.

She made us coffee, and we small talked a little bit about Dan splitting and what she was going to do next. She said she wanted to move her old bedroom furniture from the basement to her bedroom, and take the furniture she had in there now to storage. That day we move all her existing furniture to a near by storage facility she had rented. It took us most of the day. She said she could find someone else to help her move the other stuff as she did not want to burden me any more. I told her it was no problem and that if she wanted to I would stay around that evening and move the stuff.

"You are so sweet," she said and gave me a big hug.

Sheryl went to the store to grab some dinner and 12 pack of beer for us. While she was gone, I rummaged around her room. She had put her stuff in boxes while we were moving her furniture out. I looked in her closet and found a few nighties, and a lace thong body suit, but no leather or kinky looking stuff. In the back corner of her walk in closet I saw a large wood trunk. It looked very old. I tried to open it but it was locked. I remembered when were moving her other things she had taken two small keys from a drawer and put them on her bathroom counter top. I quickly retrieved them and tried them on the trunk. The second key opened the lock.

I opened the trunk to discover it was her toy box. I pulled out some of the goodies she had and looked the over. She had a several ordinary looking leather belts. All of the belts looked worn and weathered. She had a leather strap with a handle. There were two large wood paddles and blue plastic ping pong padde. In the bottom of the chest was coiled up bullwhip. The bullwhip had knots tied in the loose leather strands at the end. There was also a rod with two leather tails on the end. My cock was rock fucking hard.

I closed the trunk and put the keys back. I started moving things and thinking of how to break the ice on the whole whipping and spanking topic.

Sheryl returned from the store. We had a bite to eat and each had a few beers. The beer caused me to both lose my motivation. I said maybe we could finish tomorrow.

"But, we are almost done now," she said.

"Okay, Okay," I said. "Your a real slave driver, you know," I told her.

"Damn straight, don't make me get out my bullwhip!" she said sharply.

I saw my opportunity and jumped on it, "That might be fun actually," I said giving her a look of approval. "I don't mind a little discipline from a pretty lady," I told her.

There was a pause for a moment as we looked at one another. "You better be careful what you say mister, or you might really get a whipping," she said.

"Yeah I've heard you like to crack the whip a little," I said.

"Oh really, who told you this?" she questioned. "Was it Dan?" she asked.

"No, it was actually Jessica," I told her.

"Fuck. I forgot all about telling her that stuff," Sheryl said putting her hand on her forehead. She was looking a little embarrased.

"Don't be embarrassed, I am into it too," I said.

She didn't speak, staring at the wall. Then she looked at me and said "Is that why you agreed to come out here today?"

"I wanted to come and help you anyway, but I'd be lying if I said I hadn't thought about it a lot".

She paused again, then walked over and put one hand my arm, "This is a little awkward isn't it" she said. "I never would have thought you were the submissive type."

"Oh, but I am," I said.

She looked in my eyes for a moment and said "lets do this".

I used Sheryl's shower for a quick rinse off. When I was done she told me to wait in the living room while she showered. While I was in the shower I noticed that she had tightly closed all the blinds in the house.

She emerged from the bedroom about a half hour later. She was wearing a leopard print thong and matching bra. She sat next to me on the couch and we started to make out. I had my hands all over her ass as I kissed her neck and the top of her tits. She got on top of me and started to grind her pussy against my hard cock. She seemed like she wanted to fuck right then. I thought may be she wanted to fuck and then whip me. She turned around and sat on my lap, she was leaning forward and kept rubbing my cock up and down her thong pushing it into her pussy and anus.

"Damn, I jealous of that thong," I said.

"Why is that?" she answered.

"It gets to be against your pussy and up your ass the whole time," I said.

"Oh you are a naughty pervert aren't you," she scolded me. "Should I put you over my knee and spank you, or do you need something harder to teach you your lesson?" she asked.

"Well, I would love to be spanked over your knee, but I'll take something harder too," I answered.

She moved from the couch and sat on the edge of the ottoman. She sat up nice and straight and tapped her hand on her thigh "Over my lap" she ordered. When I stood up she pulled my boxers down to my knees and then positioned me over her lap. She pushed my hard cock between her legs against her pussy. She started to spank me, alternating blows on each ass cheek. She was very heavy handed. I looked back at her face and she was totally focused on what she was doing. She spank me about 5 times on each cheek and then stop and caress my ass. This went on for about 10 minutes. She told me to get up and sit on the couch.

She stood in front and swayed her ass back and forth in front of my face, "Kiss my ass all over," she said. I obeyed. I kissed her ass from top to bottom and made sure I gave good firm kisses. Nothing wet and sloppy. She grabbed the back of my head and pushed my face into her ass until my nose was touching her thong. I could smell her wet pussy. She released my head and began to kiss her ass cheeks again.

"So you also need something harder than a spanking?" she asked.

"Would you like to give me something harder than a spanking?" I replied.

"I want to whip you, but I have to warn you I like to give it hard," she said. "I like my man to grit his teeth and take it no matter how hard I give it. That's what gets me off. Do you think your man enough to be whipped by me?" she quizzed.

"I'll submit and take it for you," I said.

Without saying a word she went to the bedroom. She came out a few minutes later. She had her bullwhip in one hand and a pair of high heeled leather boots in the other. She dropped the whip down on the couch next to me and put her foot up on the ottoman. She slipped her feet into her boots and zipped them up one at a time.

"There is just something about wearing boots when I whip a man," she said. With her boot she pushed the ottoman into the center of the large living room. "I want you to lie over the ottoman and stick you us up and present it for my whip," she said. I did as she said.

She walked to the kitchen, took a cigarette out an lit it. She stood over my naked body for a few minutes as she enjoyed her cigarette. "Don't you just hate anticipation," she said. "You have to lie there over that ottoman waiting for me to enjoy my cigarette and knowing that when I finish I'm going to give you a lashing you won't forget."

"That's cruel," I said.

"What can I say, I'm a mean bitch," she said.

"I like you that way," I replied.

"I haven't whipped you yet my dear, lets see if you still like me when I'm done."

"Oh man" I said.

She walked over to an ash tray by the banister and put out the cigarette.

She left the room for a minute and then returned without saying a word. She picked up the bullwhip from the couch and walked to across the room from me to my left. She flipped the whip out a few times to judge her distance. Then she flipped it out and let it gently fall over my ass.

"Are you ready my dear?" she asked.

"Ready as I'll ever be" I said.

She put her left leg forward and drew the bullwhip back over her right shoulder. She paused for a moment and then brought the whip down across my ass. She repeated the pattern several times. She took her time bringing the whip back and drawing it over her shoulder between each lash. It hurt but it was tolerable. After about 10 lashes she began to increase her intensity. After about 30 she coiled up the whip and walked over to me. She ran her hands over my ass. She stood next to me tapping the whip against her thigh.

"You are already getting red marks and I have not even gotten started," she said.

She walked back to the spot she had whipped me from. I watched her ass jiggle a little as she walked. I was liking this. She again put her left leg forward and brought the whip over her shoulder. This time she brought it down with more force. I could feel the knots on the end of her whip bite into my ass. She followed with more lashes at that intensity and I began to question if I would hold up. I was letting out loud yells with some of the lashes.

"Be quiet," she said.

She gave my ass a little break and began to lash the back of my legs and the sides of my hips. Those knots at the end of the whip felt like yellow jacket stings. I could feel welts raising up on my ass and legs. After working my legs over for about 20 lashes, she came back to my ass. This time she let me have it all out. She gave me ten lashes as hard as she could. I yelled in pain for the last four.

"I'm going to have to shut you up so my neighbors don't hear you," she said.

She walked over to me and dropped set her whip down on my back. She walked in front of my and slipped off her thong. She pulled my head up by my hair. "Open your mouth," she ordered. Sincerely afraid of disobeying her I opened my mouth and pushed her wet thong deep in my mouth. "That will shut you up."

She picked up the whip and this time stood directly behind me. She started whipping me again using criss crossed lashes and alternating ass cheeks with each lash. She started moderate but it was not long before she was lashing me full force again. I had to bite down hard on the thong in my mouth in order to take the pain. Every time I bit down I got a rich taste of her pussy juices that had soaked the thong. Sheryl would take a few breaks and caress my burning welted ass

After making wait as she enjoyed another cigarette she took her spot up again just to the left of me. I liked this better than when she stood behind me because I could see her. There are more beautiful women with much better bodies, but I have never seen anything hotter than this Mid 40's women standing with a bullwhip punishing me. 

She again drew the whip back and brought it down hard. This time she alternated the lashes between my ass and the back of my legs. It did not take long until she was again delivering the lashes with full force. Toward the end I could hear her grunting a little as she was bringing the whip across my flesh. She finished with a barrage of about 20 lashes as hard as she could whip me. It bit down so hard on the thong in my mouth that I thought my teeth would break. She gave me mercy only when I broke to tears.

She rolled up her whip and tossed it on the couch. "I think you've been punished enough for today." I stayed over the ottoman trying to compose myself. She kneeled next to the ottoman and gently rubbed my welted burning skin, and she pulled her thong out of my mouth.

Once she could see I was okay, she helped me up. I was so sore I could hardly move. She held my hand and led me to her bedroom. She laid me down her bed. My ass was so sore even her soft comforter felt like sand paper on it. After a few moments of her kissing me and rubbing her pussy on my cock I began to get erect again. When she had my cock hard she mounted me on top and rode me until she got off. It was painful to have her weight on top of me pushing my sore ass harder in to the bed. She fucked me hard though and got off harder than I have ever seen a woman get off.

"Are you able to get off, or are you too sore?"

"I want to try," I said.

Sheryl moved off of me and got into the doggie style position next to me on the bed. I had to move slowly but I managed to get behind her to mount her. I bent down slowly and kissed her on both ass cheeks.

"You have a gorgeous ass," I said.

"Thanks," she replied. "We can try it in the ass if you want. I haven't done it in a while and I don't know how long I can go that way, but we can try."

"OK," I said wincing a little from the pain radiating from my whipped ass.

She got up from the bed and walked to the bathroom. She came back with a small tube of KY. She took my cock in her and and rubbed the lube all over it. She stroked it and got it rock hard. She then got back on the bed in front of me. She reached back and rubbed KY on her asshole. I began slow just pushing my cock against her anus and then backing out I did this for several minutes until she relaxed enough for me to penetrate her ass. I moved my cock in and out slowly. She moaned with pleasure every time I went back and forth. I was enjoying her tight asshole so much that the pain from the whipping had left my mind.

After several more minutes of slow motion I was able to start fucking her ass hard. When I did this I came almost immediately putting my load all over her ass cheeks. She turned over on her back and pulled me in for a kiss. "That was fucking great" she said. I flopped over next to her on the bed and the pain from my ass and legs began to throb again.

"You whipped me good baby," I said.

"I warned you" she laughed. "Sorry, I won't whip you so hard next time," she said.

"So you are saying we can do this again?" I asked.

"I hope we do it a lot more," she answered.

"Me too, and you don't have to take it easy on me either," I said.

"Good then," she said as she curled up next to me and we went to sleep.
 
When we woke the next morning she sat up and surveyed the marks still on my ass and legs. "I like to admire my work." she said. As I was leaving her house that morning she said, "Just as soon as those marks go away I want you to come back for another punishment."

"I will Sheryl, so what does this make us? Should we say you're my mistress and I'm your slave?"

"How about we just say we are friends with benefits from now on," she said.

"Friends with painful benefits," I said as I rubbed my hand over raw ass cheeks over my jeans.

"See you soon," she said with a smile.

10 days later she texted me pictures from her camera phone. The first was of her ass. She was wearing the same leopard print thong she had worn the night she whipped me. 'REMEMBER THIS, COME AND GET SOME' the text read. The other was a picture of the high heeled boots she had worn. She put them on the ottoman and coiled up her bullwhip around them. The text with the picture said 'I HEARD YOU HAVE BEEN A BAD BOY AGAIN. I GUESS YOU DIDN'T LEARN YOUR LESSON. BE HERE SATURDAY AT 7PM TO GET YOU PUNISHMENT.'

 I texted back 'I DO WANT SOME MORE OF THAT ASS AND YES I HAVE BEEN A BAD BOY AGAIN.'

She responded with a video text of her cracking the bullwhip in the air. "See you Saturday, baby," I could hear her say at the end.
 
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