Straight Female / 40
Recently divorced with a young daughter, my ex husband skipped out on child support. I have a job but my paychecks go for rent, food, etc. I had a girl from work help me move into an apartment and she must have told some of our co workers about it.
One day my boss came over and told me if I needed anything he would be more than happy to help me out. His name is Bob and he is creepy as hell. He's not ugly but he has this face that makes you think about a serial killer or child m****ter at best. The other women at work would make jokes about Bob most likely having a Porn collection that would make Satan blush. Bob kept making offers for help and I kept saying no to him.
About eight months later I was informed that my daughter was going to need braces for her teeth. The Orthodontist said it would be about $3,000 to do the work. The next day I went to see Bob about working more hours to help pay for the dental work for my daughter.
I could almost read his mind when I asked for more hours. Bob said he would have to ask his boss, but they were trying to cut back on work hours as it was but he would see what he could do for me.
The following day Bob called me into his office and told me his boss said no to my request for more work hours. I just walked out of his office and went into the ladies room and cried my eyes out.
That evening I was walking to my car when Bob pulled up beside me and handed me an envelope and told me to think about it. He drove away before I even looked into the envelope. I got into my car and opened the envelope. My mouth dropped when I pulled out the banded hundred dollar bills, $3,000 to be exact. There was also a note. "Maybe we could help each other?"
I barely made it home alive thinking about "the offer" from Bob. I almost wrecked the car thinking about Bob's note. The $3,000 was mine in exchange for sex. I could barely eat dinner with my daughter that evening I was so upset thinking about Bob's offer. That night wasn't any better, I barely slept at all.
The next day I went to work, the envelope with the $3,000 was tucked down at the bottom of my purse. I decided to pass on Bob's offer and I would return the money to Bob when I had the time to get to his office.
At lunch I went upstairs to Bob's office but his secretary said that Bob wasn't in. I knew that was bs because I saw his car parked in his usual spot that morning. That evening as I walked to my car Bob pulled up beside me. I wanted to reach into my purse and give him back the envelope with the money but I didn't.
Bob invited me to dinner and I just nodded yes, the smile on his face made me cringe. He said he would pick me up at 8pm on Friday evening. He told me to wear something nice, we were going to an upscale restaurant.
Friday arrived all too soon. I got my sister to watch my daughter. I lied to my sister and told her I was invited for a sleepover with one of the girls from work. My sister said it would be good for me and took my daughter without question.
I began to dress for the date. I had a little black dress that I didn't want to wear but it was the nicest dress I had, I would wear that for my ex husband when we went out. I barely used any makeup, I didn't want to overdue this one bit. I slipped into my heels and Bob was at my door within the hour.
Bob was dressed up but his facial features still made me feel nervous. We went to dinner and he made sure I had a few cocktails. Even with the few drinks my heart was pounding inside my chest as we drove back to his house. Bob offered me another drink and I gladly accepted, the drink was strong but I didn't care.
He finally made his move on the sofa. His large hand sliding along my stocking thigh and up under the hem of my dress. He kissed me a few moments later and his hands found the curves of my breasts.
Then he took my hand and pulled me to my feet and lead me to his bedroom. There on the walls were pictures of men and women in various sexual positions. Bob turned me around and unzipped my dress, it hit the floor at my heels silently. My bra was next, he pulled the straps down my arms. I was down to my panties, stockings and heels now.
Bob guided me to the bed and he climbed on top of me. His hands and mouth were everywhere on my body. Within moments Bob was breathing heavy as his mouth sucked and bit my nipples. At some point Bob got off the bed and undressed quickly.
When his boxer shorts hit the floor I saw his fully erect cock. It wasn't the longest I had seen, but god it had to be the thickest. His cock was thick, the head of his engorged cock was weird, as if the swollen head was split almost in two. He took it in hand and stroked it.
He looked at me as he squeezed it, the pee hole opened wide. Bob knelt on the bed and I knew what he wanted. It took me a moment before I took hold of his engorged cock. It felt heavy and it filled my hand as I wrapped my fingers around his thick shaft.
The swollen head stretched my mouth as I began to try to suck his cock. I couldn't get much of it inside it was so thick. Bob didn't seem to mind, he just told me to suck it. I did the best I could and then Bob told me to stick my tongue into his pee hole. Bob took his fingers and spread the head of his cock. My mouth dropped as I saw this huge gaping pee hole. He told me to do it. I put my tongue into his pee hole almost without effort. His hands on my head now as I pushed my tongue in as best as I could.
Then Bob was between my legs and licking my pussy. I was dry but I will admit Bob knew how to get me wet. I climaxed within a short time and he made me cum two more times. Then he was ready to fuck me. Bob spread my legs and pushed the thick head of his cock into my pussy.
I remember almost screaming, I felt like his cock was tearing my labia trying to enter my pussy. Then he was inside and he began to fuck me hard and fast. I closed my eyes, I couldn't look at him fuck me. His facial features were even more scary now his cock was buried inside of my pussy.
Bob grunted as he ravaged me, he used his cock like a weapon and suddenly I was having a mind blowing orgasm. He pulled out and then handed me a thumb size dildo vibe. Bob lay on his back and told me to fuck his cock with it.
He reached down and separated the bulb like head to expose the gaping pee hole. He smiled and nodded. I put the rounded vibe to his pee hole and pushed. Bob immediately groaned with pleasure and I slowly shoved half of the small vibe into his cock. Bob thrashed around and moaned with pleasure, precum poured out of his thick cock.
Within a few minuted Bob pushed me away and forced me onto my back. Kneeling next to my body he began to jerk his thick cock feverishly. Bob threw back his head and groaned loudly as this thick mass of cum exploded from his cock.
He jerked his cock as a never ending stream of cum erupted all over my breasts and stomach. it seemed to pour all over me for several moments. Then he just suddenly knelt beside me with his head slumped forward, breathing rapidly as I watched thick strands of cum dripping out of his large pee hole.
I sat up and pushed Bob onto the bed and straddled him quickly. His spent cock was still mostly hard enough to ride. I climaxed again before his thick cock finally gave out. Oh god it hurt and it still felt wonderful at the same time.
Bob and I have been fucking for six months now, and he helps me financially from time to time when I get into a bind. Yes I do it for the money, but now I would let Bob fuck me even if money wasn't involved.
One day my boss came over and told me if I needed anything he would be more than happy to help me out. His name is Bob and he is creepy as hell. He's not ugly but he has this face that makes you think about a serial killer or child m****ter at best. The other women at work would make jokes about Bob most likely having a Porn collection that would make Satan blush. Bob kept making offers for help and I kept saying no to him.
About eight months later I was informed that my daughter was going to need braces for her teeth. The Orthodontist said it would be about $3,000 to do the work. The next day I went to see Bob about working more hours to help pay for the dental work for my daughter.
I could almost read his mind when I asked for more hours. Bob said he would have to ask his boss, but they were trying to cut back on work hours as it was but he would see what he could do for me.
The following day Bob called me into his office and told me his boss said no to my request for more work hours. I just walked out of his office and went into the ladies room and cried my eyes out.
That evening I was walking to my car when Bob pulled up beside me and handed me an envelope and told me to think about it. He drove away before I even looked into the envelope. I got into my car and opened the envelope. My mouth dropped when I pulled out the banded hundred dollar bills, $3,000 to be exact. There was also a note. "Maybe we could help each other?"
I barely made it home alive thinking about "the offer" from Bob. I almost wrecked the car thinking about Bob's note. The $3,000 was mine in exchange for sex. I could barely eat dinner with my daughter that evening I was so upset thinking about Bob's offer. That night wasn't any better, I barely slept at all.
The next day I went to work, the envelope with the $3,000 was tucked down at the bottom of my purse. I decided to pass on Bob's offer and I would return the money to Bob when I had the time to get to his office.
At lunch I went upstairs to Bob's office but his secretary said that Bob wasn't in. I knew that was bs because I saw his car parked in his usual spot that morning. That evening as I walked to my car Bob pulled up beside me. I wanted to reach into my purse and give him back the envelope with the money but I didn't.
Bob invited me to dinner and I just nodded yes, the smile on his face made me cringe. He said he would pick me up at 8pm on Friday evening. He told me to wear something nice, we were going to an upscale restaurant.
Friday arrived all too soon. I got my sister to watch my daughter. I lied to my sister and told her I was invited for a sleepover with one of the girls from work. My sister said it would be good for me and took my daughter without question.
I began to dress for the date. I had a little black dress that I didn't want to wear but it was the nicest dress I had, I would wear that for my ex husband when we went out. I barely used any makeup, I didn't want to overdue this one bit. I slipped into my heels and Bob was at my door within the hour.
Bob was dressed up but his facial features still made me feel nervous. We went to dinner and he made sure I had a few cocktails. Even with the few drinks my heart was pounding inside my chest as we drove back to his house. Bob offered me another drink and I gladly accepted, the drink was strong but I didn't care.
He finally made his move on the sofa. His large hand sliding along my stocking thigh and up under the hem of my dress. He kissed me a few moments later and his hands found the curves of my breasts.
Then he took my hand and pulled me to my feet and lead me to his bedroom. There on the walls were pictures of men and women in various sexual positions. Bob turned me around and unzipped my dress, it hit the floor at my heels silently. My bra was next, he pulled the straps down my arms. I was down to my panties, stockings and heels now.
Bob guided me to the bed and he climbed on top of me. His hands and mouth were everywhere on my body. Within moments Bob was breathing heavy as his mouth sucked and bit my nipples. At some point Bob got off the bed and undressed quickly.
When his boxer shorts hit the floor I saw his fully erect cock. It wasn't the longest I had seen, but god it had to be the thickest. His cock was thick, the head of his engorged cock was weird, as if the swollen head was split almost in two. He took it in hand and stroked it.
He looked at me as he squeezed it, the pee hole opened wide. Bob knelt on the bed and I knew what he wanted. It took me a moment before I took hold of his engorged cock. It felt heavy and it filled my hand as I wrapped my fingers around his thick shaft.
The swollen head stretched my mouth as I began to try to suck his cock. I couldn't get much of it inside it was so thick. Bob didn't seem to mind, he just told me to suck it. I did the best I could and then Bob told me to stick my tongue into his pee hole. Bob took his fingers and spread the head of his cock. My mouth dropped as I saw this huge gaping pee hole. He told me to do it. I put my tongue into his pee hole almost without effort. His hands on my head now as I pushed my tongue in as best as I could.
Then Bob was between my legs and licking my pussy. I was dry but I will admit Bob knew how to get me wet. I climaxed within a short time and he made me cum two more times. Then he was ready to fuck me. Bob spread my legs and pushed the thick head of his cock into my pussy.
I remember almost screaming, I felt like his cock was tearing my labia trying to enter my pussy. Then he was inside and he began to fuck me hard and fast. I closed my eyes, I couldn't look at him fuck me. His facial features were even more scary now his cock was buried inside of my pussy.
Bob grunted as he ravaged me, he used his cock like a weapon and suddenly I was having a mind blowing orgasm. He pulled out and then handed me a thumb size dildo vibe. Bob lay on his back and told me to fuck his cock with it.
He reached down and separated the bulb like head to expose the gaping pee hole. He smiled and nodded. I put the rounded vibe to his pee hole and pushed. Bob immediately groaned with pleasure and I slowly shoved half of the small vibe into his cock. Bob thrashed around and moaned with pleasure, precum poured out of his thick cock.
Within a few minuted Bob pushed me away and forced me onto my back. Kneeling next to my body he began to jerk his thick cock feverishly. Bob threw back his head and groaned loudly as this thick mass of cum exploded from his cock.
He jerked his cock as a never ending stream of cum erupted all over my breasts and stomach. it seemed to pour all over me for several moments. Then he just suddenly knelt beside me with his head slumped forward, breathing rapidly as I watched thick strands of cum dripping out of his large pee hole.
I sat up and pushed Bob onto the bed and straddled him quickly. His spent cock was still mostly hard enough to ride. I climaxed again before his thick cock finally gave out. Oh god it hurt and it still felt wonderful at the same time.
Bob and I have been fucking for six months now, and he helps me financially from time to time when I get into a bind. Yes I do it for the money, but now I would let Bob fuck me even if money wasn't involved.
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