In my line of work, I don’t get to choose where in the country I want to work. Recently, I was set up to work in a fairly remote area. There were no big cities around, so I had to live in a town of just 500 people. After checking out the two bars, and hanging out at all of the public areas, I did not have any luck picking up a date. So I decided to try a new route.
I had not looked into online personal ads before, but after hearing about it from a friend back home I figured I would check it out. I went to Craigslist, and found the nearest “big” city listed. I hoped I didn’t have to drive an hour just to get laid, but I had to try something. After scouring all of the ads, and sending messages to a dozen women, I still did not find anything great. Then after about two weeks, my luck had changed.
The posting read “Older BBW wants to get raped- 62- (SR295)”. Immediately my heart started pounding and my pants got tighter. I read through the post and immediately sent her a message. After four messages back and fourth, she was ready to go. I found out that she was a 62 year old widow who was living in a small farmhouse out on a state road nearby. At 5 foot 2 and 170 pounds, her picture did not present the figure first brought to mind when I read BBW. Her 38D-30-36 proportions set my mouth drooling and wondering how I could be so lucky. With shoulder length salt and pepper hair, creamy white skin, “Sandy” had looks to die for, maybe that is why she is a widow.
She had gotten married at just 17, before her husband left for Vietnam, and stayed faithful to him from the then, all the way until now, four years after he had already passed away. We had lengthy discussions on what she had in mind, and I was all for giving her what she wanted. She was taught all her life that men brought home the bacon, and women cooked, cleaned and served the man in the bedroom. I found out that she was apparently very experience in oral sex, but had never received it back. She loved her husband, but was upset at the fact that her husband only did two things, doggy, and missionary.
Sandy said that while she would like this to be ongoing , and she wanted to catch up on a whole lot of experimenting later on, she had just one fantasy for the first meeting. She said that since she felt she had been a piece of property for 41 years, why not take it one step further. She wanted to be raped. So she gave me her address, the time she would be out doing yard work, and 2 rules. She insisted that I use a condom, seeing as it is the first time we would meet. However I had also found out that she had never used condoms with her husband since after a few years of trying, they found out he was sterile. The second rule was her safe word; FREEZE. I found her to be well educated on the subject of rape fantasy, but she let me know all of the sites online that she was reading about it, and I also found out that I would soon be only the second man to enter into this woman.

So that is how I find myself hiding behind some brush, peering through at this gorgeous woman pulling weeds from her flower bed. I was ready to go. When she moved around out of view, I ran up to the bushes next to the porch and waited. It was then that it hit me, I left my rubbers in the car, and I only had the one in my wallet. Too late now, I’ll cross that bridge when I come to it. Sandy came back around the house, and walked up to the steps, she turned around and looked out to the road, to see if I had arrived yet. NOW! I ran up behind her and covered her mouth with one hand and held her against me with the other.
“Don’t say anything or you won’t be waking up tomorrow.” Then to be sure I said “Are you ready for this Sandy?”
She nodded. With that I walked her up the stairs and into the house. Once inside, I let her go and closed the door.
“Get upstairs!” I shouted
She looked genuinely shocked and slowly backed up the stairs. The stairs led straight up into the bedroom, then I grabbed her by the arm and pushed her into the bathroom.
“You’ve got two minutes”
I didn’t want her to be uncomfortable while I was raping her, however much sense that makes. I removed my jacket and shirt, counted in my head and then I burst into the bathroom.
“Time’s up! Get in here!”
I grabbed her arm again and pulled her into the bedroom. I tried to stay in character as my eyes fell upon her body. I turned her around and undid the ties on her checkered apron. Then I undid the button and lowered the zipper on the back of her full length blue skirt.
I spun her back around as her skirt fell to the floor and pulled her apron off from around her neck.
“Please stop, somebody help me!” She screamed.
I pushed her onto the bed. “Shut up or I’m going to make this hurt.” I said calmly as I straddled her waist, holding her down. I ripped open her sheer white blouse, and leaned down, planting a kiss on her mouth. She started to kiss me back, and then stopped herself trying to stay in the fantasy. She turned her head to take her lips away from me.
“So that’s how you wanna play this,… alright” I said as I flipped her onto her stomach. I pulled her blouse off of her arms and unhooked her bra. Then I pushed off and moved down to her hips. I hooked my fingers under the waistband of her white cotton panties, and slid them off her legs, taking her shoes off at the same time. I moved over to kneel next to her and I started caressing the length of her body.
She started to roll over, so I put my hand on her back, holding her down. “Where do you think you’re going?”
I took my other hand and slid it in between her legs. I found a thick mound of pubic hair waiting for me, which I pushed through finding her lips dripping already. I pushed in further reaching her love button. I started to rub it, immediately getting a shudder from her body. After working her button for a short time, I swiftly plunged three fingers into her canal.
Sandy let out a short squeal and then buried her face into the bedspread as I stroked into her. I could feel myself about ready to break my zipper, and I thought to myself, “Rapists don’t have to last all night, I’m ready for the main event!”
“Stay down!” I commanded as I withdrew my hand and stood up. I kicked my shoes off and dropped my pants. I reached into the pocket of my jeans and got my wallet out as I stepped out of my pants. I had that rubber on in record time and jumped back on top of her, straddling her legs. I reached over and grabbed a pillow, and then I lifted her up shoving it under her stomach. Then I let her down and repositioned myself. I pinned her legs together and pressed forward sliding my cock between her legs.
“FREEZE!” Sandy shouted.
“Damn it!” I thought to myself. She’s going to back out. She’s having second thoughts.
She rolled over, pulling my dick out from between her legs. She looked down to check that there was a condom on my penis, and the proceeded to roll back onto her stomach.
“O.K….go” She said, with her voice quivering, and then pressed her face back into the bed.
“Thank god!” I said to myself.
I grabbed my dick and guided it back in between her legs. I carefully positioned it at her entrance, and then proceeded to slam the length of my cock into her with one push. I was amazed at the amount of juices that gushed out of her as I entered. She let out a short scream, and I proceeded to violently thrust my manhood into her surprisingly tight vagina.
After pumping away for what seemed like an hour, I decided I wanted to get deeper. I pulled out and flipped her over. I pulled her legs apart and immediately entered again.,
“Please, stop!” she cried out, with a tear running down her cheek. I reached up and pinned her wrists down. I worked my knees out to lift up her legs, and started pounding. I could reach a lot deeper now and I could feel the tip of my penis contacting her cervix. I continued to thrust as I stretched out my tongue and licked the tear from her face.
I pulled out of her and stood up. I grabbed her behind her knees and quickly pulled her to the edge of the bed. I lifted her legs and pressed her knees up to he breasts. I held her knees with one arm and reached down to her cunt lips. I wiped up some juices and spread them onto her anus. I slid my middle finger into her ass to lube it up a little. I then pulled out my finger and pressed my penis to her tight little rose bud. I slowly slid my manhood in until the just the head was inside. I then brought my hand back up and started working her nipples. I pinched them and rolled them around while Sandy started to moan. I continued to slowly sink the rest of my shaft in until I was buried all of the way.
She continued to cry, as I started thrusting into her ass. I picked up the pace and I could hear my balls slapping against her ass. I reached down, grabbing her ankles and lifting them up over my shoulders as I stood up. I continued to pound away until the worst happened. I felt the condom tear as I was thrusting into Sandy’s extremely tight asshole.
I continued to push into her, watching her face. It didn’t look like she noticed. By this time, the sun had set, and the room was getting dark. I pulled out of her rear end and quickly slipped the broken condom off. Meanwhile I took the other hand and wet it with the juices that were continuing to flow, soaking her pubic hair. I then switched hands, and started rubbing her clitoris, while I slicked down my now bare penis. I set it at her entrance once again, and quickly thrust myself inside of her, keeping a rapid pace. I figured she may not notice if I kept it moving. I continued to pound away to the point of exhaustion. I could not keep my pace going, but I was on the verge of climaxing.
Just before I could reach the top, I felt her hand rubbing against my cock. She had noticed the difference now that I was slowing.
“No, no…..ahh,…ff,…freeze,…FREEZE….FREEZE!” she slowly came out of her comatose state.
But it is too late now.
“No, really, STOP!” she cried out.
I leaned forward and put my hand over her mouth. I guess it was real now. I continued to pound away. I threw her legs over to the side and picked up the pace as I thrust into her. I took my hand off of her mouth and grabbed her arm.
She started to cry as I held her on me. I was almost there, when I felt her start to squeeze tightly. Her body was clenching tight and she started to scream out as tears continued to roll down her cheeks.
Watching her cry as she orgasmed , all the while I was actually raping her! There was no reason to stop now. I was already there. She squeezed down once again as I erupted inside of her. I exploded load after load into her canal.
I collapsed on top of her, holding myself inside, until I started to soften. I pulled my cock out of her and she just laid there. I quickly got dressed and left. It was over as quickly as it had started. I knew that I had gone too far, but I wondered what would come of it. I did worry that there would be some serious trouble ahead, but I had not told Sandy my real name, or given her any real information to find me with, so I hoped that would help.
When I got home from work the next day, Sandy had left me an e-mail. The subject read: “So when are you free?”

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