Jennifer is 34, blonde, 34D breast with a tattoo on her left one. She is married with one child, and she works for me.
I am 51, with salt and pepper hair, mustache and beard, slightly overweight and most importantly infatuated with Jennifer. After years of harmless flirting, I decided to try and take it to the next level. Would it work? I didn’t know, but I knew there was a possibility. I knew her marriage was not perfect. I also knew that when she read “50 Shades Of Grey”, it aroused her. So would she be the sub to my dom? I just had to find out.
Her husband was leaving town for the weekend, so I called her into my office and found out about his trip. He was headed to Colorado for the weekend, and would be leaving at about noon on that same day. About three o’clock, I called her back into my office.
“Jennifer, I need to talk to you away from work. Meet me at for dinner tonight at the Olive Garden at eight,” I told her.
“I don’t know that I can,” she started, “I have to find a sitter, and I was going to…”
I cut her off. “This is not a request Jennifer! You will meet me there at eight, I suggest you find a place for your daughter to spend the night.” She stood looking at me.
“You can go now, as a matter of fact, go ahead and take the rest of the day off.”
I reached in my wallet, and handed her a two one hundred dollar bills. “Take this and get you a new dress, and your hair done so you look as beautiful for our date as I know you can.”
She took the money and looked from it to me a couple of times. “Something that shows a little leg, and something that shows cleavage would be great, now go on.”
Jennifer left my office and then I watched as she shut down her computer system, collected her things and left, looking back over her shoulder in my direction as she did. I sat at my desk and rubbed my stiff cock through my slacks. The day ended and I went home, relaxed a bit, showered and then left my house about an hour early. I stopped and bought Jennifer flowers and then headed to the restaurant. I then got my name on the list and waited.
Just before eight, Jennifer walked in and I got out of my chair and met her as she came through the door. The dress was perfect, cut low on top and just off the shoulders with lots of her mounds showing. The dress was just about knee length and had a slit up the right leg to her mid thigh. Her hair was cut and styled. She was a walking wet dream!
I handed her the flowers I had got for her and kissed her on the cheek; she blushed a little as I did. Just then my buzzer went off indicating our table was ready, and we were then seated in a booth. I let her get in, and slide in beside her. We ordered wine and appetizers then made small talk while we waited. The waiter brought them and then took our order. While we enjoyed our wine, I put my hand on Jennifer’s knee. I felt her tense up. I did not move my hand and neither did she.
I told her, “I know you love your husband, and I know your relationship has it’s ups and downs. I also know there are some desires you have that he won’t or just satisfy for you. I don’t want to love you, that is his place, I want to satisfy those desires for you.”
She looked at her wine glass but did not move nor acknowledge what I was saying, bit I saw her nipples stiffen as I talked.
“Tonight is the night you give yourself to me.” I started. “You will be mine, not my girlfriend, not my lover, but tonight you will be my property, you will be my cumslut, my fuck toy, my whatever I want you to be. Is that understood.”
Her breathing had gotten more rapid and she was blushing, not just her cheeks, but she was blushing down to her cleavage. Still she looked at her wine glass and fidgeted with it, but she did not respond.
“Is that understood,” I repeated.
“Yes,” she breathed as she turned her head and looked me in the eyes. “I am yours and I will willingly do what you demand.”
“Good.”
I started as I put my arm around her and pulled her to me. As I did I let my hand slide inside the top of her dress and felt her nipple. As my fingers brushed across it, it hardened even harder. I didn’t think that would have been possible, but it did. As I was playing with her breast, the waiter brought our meal. He had a hard time concentrating on placing the meals while staring at what my hand was doing. As we were in the last booth and seated away from all other guest, except those directly across from us, I lifted Jennifer’s tit out of the dress, and asked the waiter if he liked her tattoo.
He just smiled and said he did.
I let go and as he walked away, I told Jennifer to cover it back up and enjoy her dinner. She was beet red as she did as she was told.
“Have you ever done anything like that before?” I asked.
“Never,” she replied.
“Did it excite you?”
“Yes, very much.”
All through dinner, I had my hand on her leg and stroked her thigh. She was wearing thigh high hose, and before we were finished, I had reached the tops of the stockings and was rubbing her bare leg. After we finished dinner and were drinking an after dinner wine, I asked was she wearing panties. She said she was.
I told her to go to the restroom and take them off and bring them back with her. When she returned, she handed me the panties which was a green lacey thong. I placed them on the edge of the table and laid the ticket on top of it; a special tip for our waiter.
I had rented a hotel for the weekend and I told Jennifer which one it was, and told her to follow me in her car, so that someone she knew would not drive by and see it sitting in the parking lot. When we got to the hotel, we went inside pressed the call button on the elevator. As we waited, we started kissing and I reached down and squeezed her ass cheeks. The door to the elevator opened and we stepped inside. I then grabbed the dress bottom and lifted it off of her. She stood on the elevator totally naked except for her heels. You could see the panic in her eyes.
I chuckled a bit. I leaned over and kissed her again and then looked deep into her eyes and told her, “This is just part of what your weekend will be like.”
Jennifer shuddered deep and her nipples stood erect as what I said registered.
Her reply was, “Yes, Master.”
She was mine, now to see just how much of her she would be willing to give me.
We reached the 10th floor and the elevator door opened. I grabbed her hand and we stepped out of the elevator together. As we stepped out, there was a group of six men waiting to get on. Their comments caused Jennifer to blush all over, and was a sence of pride for me. I knew how she looked, and I knew that she didn’t think she was that great.
The, “Oh damn” and, “Fuck, I want that” and other words were having an effect on both of us.
The door to the elevator closed as we walked down the hall and as I looked back, I saw the guys had failed to get on but were busy watching Jennifer.
“Walk back and give each of them a French kiss, then come back here,” I told her.
She started to protest, and I reminded her, “You are mine to do with what I want, remember. This is what I want.”
She replied, “Yes Master.”
She then went up to the group of men, all who looked college age and gave each one a French kiss. As she kissed each one, they took the opportunity to feel her bare tits, ass or slide a finger in her pussy.
I am 51, with salt and pepper hair, mustache and beard, slightly overweight and most importantly infatuated with Jennifer. After years of harmless flirting, I decided to try and take it to the next level. Would it work? I didn’t know, but I knew there was a possibility. I knew her marriage was not perfect. I also knew that when she read “50 Shades Of Grey”, it aroused her. So would she be the sub to my dom? I just had to find out.
Her husband was leaving town for the weekend, so I called her into my office and found out about his trip. He was headed to Colorado for the weekend, and would be leaving at about noon on that same day. About three o’clock, I called her back into my office.
“Jennifer, I need to talk to you away from work. Meet me at for dinner tonight at the Olive Garden at eight,” I told her.
“I don’t know that I can,” she started, “I have to find a sitter, and I was going to…”
I cut her off. “This is not a request Jennifer! You will meet me there at eight, I suggest you find a place for your daughter to spend the night.” She stood looking at me.
“You can go now, as a matter of fact, go ahead and take the rest of the day off.”
I reached in my wallet, and handed her a two one hundred dollar bills. “Take this and get you a new dress, and your hair done so you look as beautiful for our date as I know you can.”
She took the money and looked from it to me a couple of times. “Something that shows a little leg, and something that shows cleavage would be great, now go on.”
Jennifer left my office and then I watched as she shut down her computer system, collected her things and left, looking back over her shoulder in my direction as she did. I sat at my desk and rubbed my stiff cock through my slacks. The day ended and I went home, relaxed a bit, showered and then left my house about an hour early. I stopped and bought Jennifer flowers and then headed to the restaurant. I then got my name on the list and waited.
Just before eight, Jennifer walked in and I got out of my chair and met her as she came through the door. The dress was perfect, cut low on top and just off the shoulders with lots of her mounds showing. The dress was just about knee length and had a slit up the right leg to her mid thigh. Her hair was cut and styled. She was a walking wet dream!
I handed her the flowers I had got for her and kissed her on the cheek; she blushed a little as I did. Just then my buzzer went off indicating our table was ready, and we were then seated in a booth. I let her get in, and slide in beside her. We ordered wine and appetizers then made small talk while we waited. The waiter brought them and then took our order. While we enjoyed our wine, I put my hand on Jennifer’s knee. I felt her tense up. I did not move my hand and neither did she.
I told her, “I know you love your husband, and I know your relationship has it’s ups and downs. I also know there are some desires you have that he won’t or just satisfy for you. I don’t want to love you, that is his place, I want to satisfy those desires for you.”
She looked at her wine glass but did not move nor acknowledge what I was saying, bit I saw her nipples stiffen as I talked.
“Tonight is the night you give yourself to me.” I started. “You will be mine, not my girlfriend, not my lover, but tonight you will be my property, you will be my cumslut, my fuck toy, my whatever I want you to be. Is that understood.”
Her breathing had gotten more rapid and she was blushing, not just her cheeks, but she was blushing down to her cleavage. Still she looked at her wine glass and fidgeted with it, but she did not respond.
“Is that understood,” I repeated.
“Yes,” she breathed as she turned her head and looked me in the eyes. “I am yours and I will willingly do what you demand.”
“Good.”
I started as I put my arm around her and pulled her to me. As I did I let my hand slide inside the top of her dress and felt her nipple. As my fingers brushed across it, it hardened even harder. I didn’t think that would have been possible, but it did. As I was playing with her breast, the waiter brought our meal. He had a hard time concentrating on placing the meals while staring at what my hand was doing. As we were in the last booth and seated away from all other guest, except those directly across from us, I lifted Jennifer’s tit out of the dress, and asked the waiter if he liked her tattoo.
He just smiled and said he did.
I let go and as he walked away, I told Jennifer to cover it back up and enjoy her dinner. She was beet red as she did as she was told.
“Have you ever done anything like that before?” I asked.
“Never,” she replied.
“Did it excite you?”
“Yes, very much.”
All through dinner, I had my hand on her leg and stroked her thigh. She was wearing thigh high hose, and before we were finished, I had reached the tops of the stockings and was rubbing her bare leg. After we finished dinner and were drinking an after dinner wine, I asked was she wearing panties. She said she was.
I told her to go to the restroom and take them off and bring them back with her. When she returned, she handed me the panties which was a green lacey thong. I placed them on the edge of the table and laid the ticket on top of it; a special tip for our waiter.
I had rented a hotel for the weekend and I told Jennifer which one it was, and told her to follow me in her car, so that someone she knew would not drive by and see it sitting in the parking lot. When we got to the hotel, we went inside pressed the call button on the elevator. As we waited, we started kissing and I reached down and squeezed her ass cheeks. The door to the elevator opened and we stepped inside. I then grabbed the dress bottom and lifted it off of her. She stood on the elevator totally naked except for her heels. You could see the panic in her eyes.
I chuckled a bit. I leaned over and kissed her again and then looked deep into her eyes and told her, “This is just part of what your weekend will be like.”
Jennifer shuddered deep and her nipples stood erect as what I said registered.
Her reply was, “Yes, Master.”
She was mine, now to see just how much of her she would be willing to give me.
We reached the 10th floor and the elevator door opened. I grabbed her hand and we stepped out of the elevator together. As we stepped out, there was a group of six men waiting to get on. Their comments caused Jennifer to blush all over, and was a sence of pride for me. I knew how she looked, and I knew that she didn’t think she was that great.
The, “Oh damn” and, “Fuck, I want that” and other words were having an effect on both of us.
The door to the elevator closed as we walked down the hall and as I looked back, I saw the guys had failed to get on but were busy watching Jennifer.
“Walk back and give each of them a French kiss, then come back here,” I told her.
She started to protest, and I reminded her, “You are mine to do with what I want, remember. This is what I want.”
She replied, “Yes Master.”
She then went up to the group of men, all who looked college age and gave each one a French kiss. As she kissed each one, they took the opportunity to feel her bare tits, ass or slide a finger in her pussy.
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She then turned and started back towards me.
After about five steps one of the guys shouted out, “Hey Lady, turn around.”
As Jennifer did, all six of them had their camera phones ready and Jennifer stopped, kicked her hip out and stood so that they could take her picture. She then turned around and she hurried back to where I was.
As we got into the room, she took me in her arms and kissed me passionately.
“Oh Master, I am so excited. I need you to take me please, I need release, please fuck me,” she begged.
“Not yet,” I told her. “Undress me first, then show me how much you want me.”
She took off my suit coat, tie, shirt and then socks shoes and slacks. Leaving me in my boxer briefs and while I was like that, she placed her lips over the bulge my cock was making and blew her hot breath through the material. This caused me to suck in a deep breath and hiss at the same time. It felt great. She then slide down my underwear and took my 8 inch cock all the way down her throat, I could not believe she could deep throat me like that, she was good and she used her skills. She then took my cock out of her mouth and sucked first one and then the other of my balls into her mouth, then turned her attention back to my cock. I grabbed her head and started fucking her mouth. After just a couple of minutes, I held her head with her nose against my body and shot several loads into her mouth and she swallowed every drop.
I told her to get on the bed and prop several pillows behind her so she was almost sitting up. As she got comfortable, I pulled the room chair around so I was at her feet.
“Now I want you to spread your legs and masturbate for me.”
“I have never masturbated in front of anyone before," she said.
My reply was, “You have never kissed six guys you have never met while completely naked in a hotel hallway either. Now do as I said.”
“Yes, Master.”
She closed her eyes; spread her legs, and started running both hands across her breast, down to her pussy and then back up. She then moved one hand down and started rubbing her clit. She started moaning and then her other hand went down and she placed first two and then three fingers into her cunt. After just about three minutes, her hips raised up off the bed, her head thrown back and she came hard. Her hips bucked up and down and her pussy juice ran out her lips, down her ass crack and then dripped on the bed spread. As soon as she collapsed back on the bed, I jumped up and dove between her legs and planted my mouth on her pussy and started licking and sucking her to another orgasm.
As the second orgasm subsided, I pushed her legs up and had her set her feet on my shoulders. I then grabbed her ass, parted her cheeks and ran my tongue around her asshole. She tensed up again, and I kept moving my tongue around her ass until she relaxed a bit. I then jammed my tongue as deep in her ass as I could.
“Oh God,” she repeated over and over as I tongue fucked her ass.
I pulled away and rolled her over. I pulled her up on her knees and spread her legs. I then attacked her asshole again but this time, I used my hand on her clit. She screamed into the pillows as she came a third time within about 10 minutes. Before she could recover, I moved up and slammed my cock deep into her pussy. I slammed hard over and over and within just a couple of minutes I pumped her full of my seed. I collapsed beside her and pulled her to me and we soon fell asleep.
I was woke up to a warm feeling on my cock. As my eyes opened, I saw Jennifer on her knees with my cock back in her mouth. Soon she had me hard as a rock. I pulled her off me and brought her up face to face with me. We kissed.
“Hi, my little fuck toy.”
She smiled and replied, “Hi.”
“Enjoying the night so far?” I asked.
“Better than I thought it could be,” was her reply.
“Good, now you have one more hole that I need to take care of, and I have an idea for that.”
“I have never had sex there, I don’t think I can do it.”
“Look bitch, you don’t tell me what you can and can’t do. That is my job. You enjoyed my tongue, you will enjoy my cock. Now since you decided to tell me what you could or would do, you will be punished.”
I grabbed her by her tit and pulled hard, pulling her out of the bed. I took her around to the foot of the bed and pushed her over so she was bending at the waist. Before she realized what was happening, I brought my hand down hard on her bare ass cheek. She stood up and I pushed her right back over.
“Don’t you ever do that again when you are being punished.”
I then came down again over and over on her ass until every inch of her cheeks were red.
“Don’t move,” I told her as I walked over to where my clothes were laying and I took out a small tube of lube.
I then walked back to where she was bent over and instructed her to spread her ass cheeks for me. As she did, I put lube on my finger, then on her ass. Then not so pleasantly I pushed my finger deep in her asshole.
“That would have been gentle, but because you decided you could submit, you made me do it this way.”
“I understand, Master,” she cried out as I worked my finger in and out.
Soon, I was working a second finger in and she was moving her ass back to meet each thrust. She was getting into this, moaning and telling me to give it to her over and over. I then added a third finger and told her to play with herself. Soon she was on the brink of orgasm and I told her to stop before she could cum. I then smeared lube on my cock, then I pulled her off the bed by her hair and we walked over to the balcony doors. I pulled the curtain open then opened the doors. We walked out and looked around, both of us still naked.
As I looked to the right, a couple of balconies down the six guys from earlier were sitting out drinking. I moved Jennifer to where she was facing them and told her to grab the rail. She did, and I bent her at the waist again, this time I put the tip of my cock at her asshole and pushed. She gasped, and when she did one of the guys heard her. He looked our way then pointed us out to his buddies.
I pushed my cock slowly up her backdoor until I was completely buried in her. Then I started working it back and forth. Before long she started getting into it. I reached around and fondled her tits as I fucked her ass.
“Are your eyes opened or closed?” I asked.
“Closed,” she told me.
“Open them and watch them watch you getting fucked,” I told her.
She did, and as she opened her eyes and watched them, she pushed back harder.
“Fuck my ass, Master,” she said loud enough so the men could hear.
“He’s your master?” one of the guys asked.
“Yes,” Jennifer hissed back as I pumped in and out of her ass while pulling her nipples.
“Does that mean you’re his slave?”
“Yes. Oh, oh. Cum in my ass, Master. Please cum in me Master,” Jennifer began to beg, all the time looking the one who asked the questions in the eyes.
I grabbed her hips and really started pumping hard, just seconds away from filling her previously virgin ass. I then pulled her hard back to me and stiffened out as my sperm shot out my cock and deep in her bowels.
“Fuck yea, oh yea, oh yea,” Jennifer moaned and she came at the same time.
I pulled my cock out, stood her up and against me. I turned her face to me and kissed her as I squeezed her tit. Jennifer raised her arm and wrapped it around my neck and kissed me back. I then looked up and told the guys good night and hoped they enjoyed the show.
Jennifer blew them a kiss and we walked back into the room.
After about five steps one of the guys shouted out, “Hey Lady, turn around.”
As Jennifer did, all six of them had their camera phones ready and Jennifer stopped, kicked her hip out and stood so that they could take her picture. She then turned around and she hurried back to where I was.
As we got into the room, she took me in her arms and kissed me passionately.
“Oh Master, I am so excited. I need you to take me please, I need release, please fuck me,” she begged.
“Not yet,” I told her. “Undress me first, then show me how much you want me.”
She took off my suit coat, tie, shirt and then socks shoes and slacks. Leaving me in my boxer briefs and while I was like that, she placed her lips over the bulge my cock was making and blew her hot breath through the material. This caused me to suck in a deep breath and hiss at the same time. It felt great. She then slide down my underwear and took my 8 inch cock all the way down her throat, I could not believe she could deep throat me like that, she was good and she used her skills. She then took my cock out of her mouth and sucked first one and then the other of my balls into her mouth, then turned her attention back to my cock. I grabbed her head and started fucking her mouth. After just a couple of minutes, I held her head with her nose against my body and shot several loads into her mouth and she swallowed every drop.
I told her to get on the bed and prop several pillows behind her so she was almost sitting up. As she got comfortable, I pulled the room chair around so I was at her feet.
“Now I want you to spread your legs and masturbate for me.”
“I have never masturbated in front of anyone before," she said.
My reply was, “You have never kissed six guys you have never met while completely naked in a hotel hallway either. Now do as I said.”
“Yes, Master.”
She closed her eyes; spread her legs, and started running both hands across her breast, down to her pussy and then back up. She then moved one hand down and started rubbing her clit. She started moaning and then her other hand went down and she placed first two and then three fingers into her cunt. After just about three minutes, her hips raised up off the bed, her head thrown back and she came hard. Her hips bucked up and down and her pussy juice ran out her lips, down her ass crack and then dripped on the bed spread. As soon as she collapsed back on the bed, I jumped up and dove between her legs and planted my mouth on her pussy and started licking and sucking her to another orgasm.
As the second orgasm subsided, I pushed her legs up and had her set her feet on my shoulders. I then grabbed her ass, parted her cheeks and ran my tongue around her asshole. She tensed up again, and I kept moving my tongue around her ass until she relaxed a bit. I then jammed my tongue as deep in her ass as I could.
“Oh God,” she repeated over and over as I tongue fucked her ass.
I pulled away and rolled her over. I pulled her up on her knees and spread her legs. I then attacked her asshole again but this time, I used my hand on her clit. She screamed into the pillows as she came a third time within about 10 minutes. Before she could recover, I moved up and slammed my cock deep into her pussy. I slammed hard over and over and within just a couple of minutes I pumped her full of my seed. I collapsed beside her and pulled her to me and we soon fell asleep.
I was woke up to a warm feeling on my cock. As my eyes opened, I saw Jennifer on her knees with my cock back in her mouth. Soon she had me hard as a rock. I pulled her off me and brought her up face to face with me. We kissed.
“Hi, my little fuck toy.”
She smiled and replied, “Hi.”
“Enjoying the night so far?” I asked.
“Better than I thought it could be,” was her reply.
“Good, now you have one more hole that I need to take care of, and I have an idea for that.”
“I have never had sex there, I don’t think I can do it.”
“Look bitch, you don’t tell me what you can and can’t do. That is my job. You enjoyed my tongue, you will enjoy my cock. Now since you decided to tell me what you could or would do, you will be punished.”
I grabbed her by her tit and pulled hard, pulling her out of the bed. I took her around to the foot of the bed and pushed her over so she was bending at the waist. Before she realized what was happening, I brought my hand down hard on her bare ass cheek. She stood up and I pushed her right back over.
“Don’t you ever do that again when you are being punished.”
I then came down again over and over on her ass until every inch of her cheeks were red.
“Don’t move,” I told her as I walked over to where my clothes were laying and I took out a small tube of lube.
I then walked back to where she was bent over and instructed her to spread her ass cheeks for me. As she did, I put lube on my finger, then on her ass. Then not so pleasantly I pushed my finger deep in her asshole.
“That would have been gentle, but because you decided you could submit, you made me do it this way.”
“I understand, Master,” she cried out as I worked my finger in and out.
Soon, I was working a second finger in and she was moving her ass back to meet each thrust. She was getting into this, moaning and telling me to give it to her over and over. I then added a third finger and told her to play with herself. Soon she was on the brink of orgasm and I told her to stop before she could cum. I then smeared lube on my cock, then I pulled her off the bed by her hair and we walked over to the balcony doors. I pulled the curtain open then opened the doors. We walked out and looked around, both of us still naked.
As I looked to the right, a couple of balconies down the six guys from earlier were sitting out drinking. I moved Jennifer to where she was facing them and told her to grab the rail. She did, and I bent her at the waist again, this time I put the tip of my cock at her asshole and pushed. She gasped, and when she did one of the guys heard her. He looked our way then pointed us out to his buddies.
I pushed my cock slowly up her backdoor until I was completely buried in her. Then I started working it back and forth. Before long she started getting into it. I reached around and fondled her tits as I fucked her ass.
“Are your eyes opened or closed?” I asked.
“Closed,” she told me.
“Open them and watch them watch you getting fucked,” I told her.
She did, and as she opened her eyes and watched them, she pushed back harder.
“Fuck my ass, Master,” she said loud enough so the men could hear.
“He’s your master?” one of the guys asked.
“Yes,” Jennifer hissed back as I pumped in and out of her ass while pulling her nipples.
“Does that mean you’re his slave?”
“Yes. Oh, oh. Cum in my ass, Master. Please cum in me Master,” Jennifer began to beg, all the time looking the one who asked the questions in the eyes.
I grabbed her hips and really started pumping hard, just seconds away from filling her previously virgin ass. I then pulled her hard back to me and stiffened out as my sperm shot out my cock and deep in her bowels.
“Fuck yea, oh yea, oh yea,” Jennifer moaned and she came at the same time.
I pulled my cock out, stood her up and against me. I turned her face to me and kissed her as I squeezed her tit. Jennifer raised her arm and wrapped it around my neck and kissed me back. I then looked up and told the guys good night and hoped they enjoyed the show.
Jennifer blew them a kiss and we walked back into the room.
