My Date With Ben - Part 2 free porn video
I got a call from Ben Monday morning, and he needed to talk to me urgently. His wife was going to be coming to the proposal meeting that he had talked about and she was looking forward to seeing me there. Ben asked if I would be able to be free for the day on Thursday. My work schedule was light, and the thought of going to a business meeting with them seemed interesting, so I accepted. Ben promised that if everything went smooth and his company won this project, that he would reward me handsomely for my efforts.
Ben offered me a trip to a local day spa for the day before to get ready, and that he was going to get things set up with the consulting firm that he had talked about. I accepted and took down all the information he was telling me.
Wednesday afternoon I left my work early and headed home to get ready for the spa. I quickly changed into leggings, an oversize sweater, and some ugg boots, before I headed to the spa. I also applied some simple base make-up and touched up my lips and eyes, and pulled my hair back into a ponytail. When I arrived, the girl at the receptionist desk, checked me in and sent me to the back to change into a robe.
A salon worker met me and gave me the full package of facial, manicure and pedicure, and I ended with a full body scrub with a chocolate sugar mixture that smelled delicious. She asked me if I had any special plans, and I said that I had a big business meeting the next day and needed to relax to be ready for it. She smiled and told me good luck with my meeting.
I left and went home and enjoyed the feeling of being pampered. I had been practicing walking in my new tall pumps all week, and I put them on again to continue to try and improve. I felt so sexy and was looking forward to the next day. I ended up stroking myself and climaxed while picturing what was going to happen tomorrow.
The next day I got up early and grabbed a long shower. I still had the faint smell of chocolate on me and I didn’t want that for today’s meeting. I grabbed one of my smallest corsets and struggled to get it on, but I wanted to look my best for the day’s events. It was a black one with red lace on the front panels. It made my breasts look larger, and I wanted that for today.
I then put on a spandex thong pair of panties and slid some nude nylons up my legs and attached them to the garters on the corset. I sat at my vanity and did my make-up, going for the professional woman look as best I could. I used just a hint of eye shadow and went with the pink lipstick again for the day. I stayed with the same hairstyle as Ben and his wife had seen me with last Saturday.
I picked out a simple gold necklace and bracelet set and went with a pair of fake diamond earrings that I had bought from QVC. My nerves were getting to me, so I took a valium to help calm me down for the day. I then slipped into the navy dress that Ben’s wife thought I looked best in. After studying myself in the mirror, I had to agree that she did make a good choice, although I wasn’t my personal favorite style. I did look like a successful professional female engineer.
I stepped in to the three and half inch black leather heels that Ben had bought for me and walked around a little bit. I was getting more comfortable in them and did like the way they make my legs look wearing them. I grabbed a purse and a small portfolio and then grabbed a long coat and headed out for the day.
I drove over to the office of the consultants that Ben had said I worked for. He told me that he had talked with the owner of the company and that he had explained that he was bringing me to the meeting as a new project manager that he had hired to help with the project. The owner was a guy named Mike who had agreed to go along with the understanding that he would be compensated for his efforts also. When I got to the building, it was a small office with about a dozen cars parked outside.
I checked myself out in the mirror again and then walked into the office. I introduced myself as Erica and was here to see Mike. He came quickly out and took me back to his office. He explained to me that Ben had talked him into this, but he wasn’t sure how it was going to go. I explained that I was a recent acquaintance of Ben’s, but that he thought I could help the team get the project. Mike gave me a copy of their part of the project and told me to read up on it in case I was asked any questions.
He left me in the office, but was clearly studying me as he went about some other things he needed to get done. After about thirty minutes, he said that we needed to leave and that I would be riding with him to the meeting, since we were working together. I accepted and we walked out and got in his SUV. He explained that we were meeting Ben’s company at the office of the client they were trying to land.
We made some small talk on the way over and his eyes kept wandering down to my legs. As we got near the clients office, he asked, if I was exclusive with Ben. I said that I wasn’t, but I wasn’t sure that I wanted to mix business and pleasure. He put his hand on my leg and told me that he would guarantee my pleasure if I would ever go on a date with him. I laughed, thanked him for the offer, and slid his hand back off of my leg. I told him we could talk on the way back after the meeting.
We met Ben and his company’s group, which had about six other people, including his wife, in the parking lot of the client’s high rise office. We made some introductions and then headed in to the building. Ben’s wife, Susie, told me how attractive the dress was that I had chosen, and that she liked my style, and gave me a wink. I thanked her and told her that a stylish friend I knew had helped me pick it for the day. She smiled back at me with that compliment.
We had to ride an elevator up several floors to get to the meeting room. When we piled into the elevator, Ben ended up beside me, and slid his hand along my but several times on the way up the elevator. I looked own and could see that he was sprouting a huge boner through his pants, and bumped against it to antagonize him more. I was trying to be as discrete as possible, as his wife was just on the other side of him, but she was staring at her reflection in the mirrors of the elevator.
We got to the meeting room and were shown in where four men were waiting for us. They all introduced us to each other and we began. The vice president of purchasing from the client company was a blonde surfer looking guy, named Sam, who continued to look at me almost constantly. I smiled back at him and thought about what I would be like to be with him privately. He was definitely one of the most attractive guys I had ever seen. The meeting took about an hour, and I got the feeling that things went well. I was asked one question, and I answered it quickly and quietly, thankful that Mike had given me some of the info from his company’s part of the project.
The meeting ended and as we all were getting up to leave, the guy next to me, spilled his coffee cup on the table and some splashed onto my dress. Ben gave him a glaring look, but Sam immediately offered to escort me to the ladies room where I could try to clean off the stain. I accepted and he led me through several halls to a ladies room. I went in and tried to use some water to get the stain out, but it didn’t help much.
When I came out of the restroom, Sam asked if it any better and I shook my head no. He offered to take me to his office and get some club soda to try. I accepted and we walked around the corner to his office. I was very large and on the corner of the building. He grabbed a bottle of club soda and some paper towels and asked if he could help. I said yes and he dropped to a knee and tried to blot the stain with a little club soda. I thanked him for his efforts as the stain started to disappear. I asked what I could do to repay him for his efforts to save my dress.
He smiled and asked if I would go to dinner with him sometime. I smiled and said absolutely. He told me that he was a golfing buddy of Ben’s and Ben had mentioned that he was bringing a secret weapon to today’s meeting when they had played yesterday. I sensed this was my moment so I decided to go for it.
I told him that I thought that I should be able to repay the favor now if he was up for it. He got a sheepish grin on my face and I took that as a yes. I leaned forward and gave him a soft quick kiss and reached for his groin at the same time. His cock was already hard and felt like it must have been eight or nine inches long. I unzipped his pants and slid my hand inside. His boxers were silky and his cock was definitely longer than Ben’s.
I asked if this was okay for him, and he smiled and said he was loving it. I dropped to my knees and slid his pant down so that I could get a good look at his cock. It was definitely the longest one I had ever seen, but it wasn’t very thick. I told him that I had never seen one this long, but that I would do the best I could with it. I started kissing it, and then put it in my mouth. I worked my way down, but was only able to get about two-thirds of it down my throat. He placed his hands on my head to try and help me go further down. After about four or five minutes of this, I pulled off and motioned for him to sit on his couch.
He sat on the edge of the couch, and I asked him if I could ride him to get it all the way in. He said absolutely and thanked Ben for bringing me as his secret weapon. I reached up and pulled my panties to one side as I sat down on his cock. I was riding high and he tried to push me back a little, and I told him that I wanted him in my ass, and not my pussy. He beamed at that and let me slide up so that I could impale myself on his cock.
It took a few tries of wiggling back and forth, and then his head popped inside and I slid down. It took two of my up and down movements to get him buried in my ass completely. He moaned in pleasure and said that I had the best ass he ever had. He told me that we had to be quiet, but that he wanted to fuck me so bad all meeting and he was glad we were getting to do it so quickly. He commented that he loved my ass and I started to slowly slide up and down on his cock. After only about three minutes of that, he grabbed me tight and spurted load after load of come into my ass. We kissed deeply and he thanked me for doing him. I popped up off him, and bent down to lick him clean.
After cleaning him up good, I grabbed a paper towel and wiped the come that had started to leak from my ass. He got himself dressed and composed, and promised that we would got out for dinner again sometime. He said that he was looking forward to working with our team in the future, and that we can plan on getting the contract, if he had anything to do with it. I thanked him and told him that I would love to see him again.
He walked me back out and down to the lobby where Mike was waiting for me. He apologized to Mike for keeping me so long, but had asked me few additional questions about the project and my answers were very helpful in his understanding of what our team was bringing to the table. Mike thanked him and we left. As we walked to Mike’s car, he asked what really happened. I told him that Sam just had a few questions and I helped him with them.
We drove away and my phone began buzzing with text messages from Ben. I sent him a message that the project was going to be his and I would fill him in later when I was alone. He said okay, and promised that I call him later with the details. Mike started asking me out again and I decided to call his bluff. I reached over and began to feel his crotch.
Mike’s eyes went wide and he began to smile. He asked me if I was a prostitute hired by Ben to get this job. I told him that I might be, and would he be able to keep his mouth shut if I was. He said he kept lots of secrets, and I said that was good, because I am going to suck your cock while you drive us back to the office. I told him the longer he drove, the longer I would suck his cock. He agreed and almost immediately made a turn in a different direction. I unzipped his pants and freed his cock from his underwear. It was a medium sized cock, but very thick around.
I unbuckled my seat belt and turned and put my head in his lap. I began with little kiss to the top of the head of his cock. I then kissed around it and he moaned for more. I them took him in my mouth entirely and slowly went up and down on his shaft. He continued groaning and begged for me to go faster. I leaned up and told him if I went faster, that he would come quicker and I wanted this to last for a while.
I went back to the slow up and down motion with my mouth over his cock. His groans would get deep and then light as I went up and down. After what seemed like twenty minutes, my jaw began to get sore so I started going faster. In less than thirty seconds, he started to come and filled my throat with his load. I swallowed it all down and stayed on his cock until it deflated. As I lifted my head, I thanked him for the lunch snack. He thanked me for that and offered to have me work for him anytime. I told him that the first one was free, but after that, I was a twenty-five hundred per day escort.
He stammered that he couldn’t afford that much, but I asked if he liked my blow job. He said yes, and then agreed that it would be worth it, if he got to fuck me as well. I told him that I saved my pussy for my personal life, but that I would let my business partners fuck my ass as they chose. I told him that I had never had a cock as thick in my ass as his, but that if he wanted to try, I would be willing. He agreed that he wanted to try, but admitted that it would take him some time to get hard again. I told him that I could help with that as well.
I reached back down and started sucking his cock again. Soon it started to come to life. I told him to pull over to a secluded area, as I wanted to try and have him fit that fat cock in my ass. He soon pulled over in a rest area and led me into the woods behind the building. I found a tree that was about right for me and bent over it. I pulled my dress up enough for my ass to show and slid my panties to the side and said for him to try it. He pulled out his cock and pressed against my asshole. It was still a little wet from my previous session, and he started to press in. It was getting painful as his head was fighting his way into my sphincter. I tried to relax and then it popped it and went all the way it in one stroke.
I just about fell over from the pressure and pain, but the pain quickly subsided. I asked him to go slow and he had me fuller than I had ever been. He began to work in and out and soon it became more pleasurable for me as he was hitting my prostate. He only lasted a few minutes when he came again and filled my ass with his come. As he was filling my ass, the pressure put me over the edge and I came as well. He felt me spasm on his cock and was proud that he made me come from his ass fucking.
He said that was the first time that had ever happened to him, but that it was the first time a woman ever let him fuck there ass as well. I told him it was because he was so thick and that his cock was heavenly. He enjoyed the compliments and we quickly got re-arranged and went back to his car. We drove back to his office and he asked if he could write me a check. I told him that I only accepted cash, but that I would be by on Monday to pick up my envelope. He promised that he would have it ready, and I warned him that if he didn’t, I would have to tell Ben and he would make sure that Mike paid me. Mike asked me not to tell Ben, and I said that as long as he paid me, I would keep this our secret.
I gave Mike a kiss on the lips and then got out of his car in the parking lot at his office and walked to my car. I drove home and went in and relaxed on my couch. I texted Ben to call me and he did within fifteen minutes. I gave him the brief story about Sam, and told him that the contract was probably going to be his. He thanked me profusely and asked if I could come to his house that weekend. His wife wanted to get to know me better and he said that he needed to see me again soon.
I told him I would and that story is for later.
Erica
Ben offered me a trip to a local day spa for the day before to get ready, and that he was going to get things set up with the consulting firm that he had talked about. I accepted and took down all the information he was telling me.
Wednesday afternoon I left my work early and headed home to get ready for the spa. I quickly changed into leggings, an oversize sweater, and some ugg boots, before I headed to the spa. I also applied some simple base make-up and touched up my lips and eyes, and pulled my hair back into a ponytail. When I arrived, the girl at the receptionist desk, checked me in and sent me to the back to change into a robe.
A salon worker met me and gave me the full package of facial, manicure and pedicure, and I ended with a full body scrub with a chocolate sugar mixture that smelled delicious. She asked me if I had any special plans, and I said that I had a big business meeting the next day and needed to relax to be ready for it. She smiled and told me good luck with my meeting.
I left and went home and enjoyed the feeling of being pampered. I had been practicing walking in my new tall pumps all week, and I put them on again to continue to try and improve. I felt so sexy and was looking forward to the next day. I ended up stroking myself and climaxed while picturing what was going to happen tomorrow.
The next day I got up early and grabbed a long shower. I still had the faint smell of chocolate on me and I didn’t want that for today’s meeting. I grabbed one of my smallest corsets and struggled to get it on, but I wanted to look my best for the day’s events. It was a black one with red lace on the front panels. It made my breasts look larger, and I wanted that for today.
I then put on a spandex thong pair of panties and slid some nude nylons up my legs and attached them to the garters on the corset. I sat at my vanity and did my make-up, going for the professional woman look as best I could. I used just a hint of eye shadow and went with the pink lipstick again for the day. I stayed with the same hairstyle as Ben and his wife had seen me with last Saturday.
I picked out a simple gold necklace and bracelet set and went with a pair of fake diamond earrings that I had bought from QVC. My nerves were getting to me, so I took a valium to help calm me down for the day. I then slipped into the navy dress that Ben’s wife thought I looked best in. After studying myself in the mirror, I had to agree that she did make a good choice, although I wasn’t my personal favorite style. I did look like a successful professional female engineer.
I stepped in to the three and half inch black leather heels that Ben had bought for me and walked around a little bit. I was getting more comfortable in them and did like the way they make my legs look wearing them. I grabbed a purse and a small portfolio and then grabbed a long coat and headed out for the day.
I drove over to the office of the consultants that Ben had said I worked for. He told me that he had talked with the owner of the company and that he had explained that he was bringing me to the meeting as a new project manager that he had hired to help with the project. The owner was a guy named Mike who had agreed to go along with the understanding that he would be compensated for his efforts also. When I got to the building, it was a small office with about a dozen cars parked outside.
I checked myself out in the mirror again and then walked into the office. I introduced myself as Erica and was here to see Mike. He came quickly out and took me back to his office. He explained to me that Ben had talked him into this, but he wasn’t sure how it was going to go. I explained that I was a recent acquaintance of Ben’s, but that he thought I could help the team get the project. Mike gave me a copy of their part of the project and told me to read up on it in case I was asked any questions.
He left me in the office, but was clearly studying me as he went about some other things he needed to get done. After about thirty minutes, he said that we needed to leave and that I would be riding with him to the meeting, since we were working together. I accepted and we walked out and got in his SUV. He explained that we were meeting Ben’s company at the office of the client they were trying to land.
We made some small talk on the way over and his eyes kept wandering down to my legs. As we got near the clients office, he asked, if I was exclusive with Ben. I said that I wasn’t, but I wasn’t sure that I wanted to mix business and pleasure. He put his hand on my leg and told me that he would guarantee my pleasure if I would ever go on a date with him. I laughed, thanked him for the offer, and slid his hand back off of my leg. I told him we could talk on the way back after the meeting.
We met Ben and his company’s group, which had about six other people, including his wife, in the parking lot of the client’s high rise office. We made some introductions and then headed in to the building. Ben’s wife, Susie, told me how attractive the dress was that I had chosen, and that she liked my style, and gave me a wink. I thanked her and told her that a stylish friend I knew had helped me pick it for the day. She smiled back at me with that compliment.
We had to ride an elevator up several floors to get to the meeting room. When we piled into the elevator, Ben ended up beside me, and slid his hand along my but several times on the way up the elevator. I looked own and could see that he was sprouting a huge boner through his pants, and bumped against it to antagonize him more. I was trying to be as discrete as possible, as his wife was just on the other side of him, but she was staring at her reflection in the mirrors of the elevator.
We got to the meeting room and were shown in where four men were waiting for us. They all introduced us to each other and we began. The vice president of purchasing from the client company was a blonde surfer looking guy, named Sam, who continued to look at me almost constantly. I smiled back at him and thought about what I would be like to be with him privately. He was definitely one of the most attractive guys I had ever seen. The meeting took about an hour, and I got the feeling that things went well. I was asked one question, and I answered it quickly and quietly, thankful that Mike had given me some of the info from his company’s part of the project.
The meeting ended and as we all were getting up to leave, the guy next to me, spilled his coffee cup on the table and some splashed onto my dress. Ben gave him a glaring look, but Sam immediately offered to escort me to the ladies room where I could try to clean off the stain. I accepted and he led me through several halls to a ladies room. I went in and tried to use some water to get the stain out, but it didn’t help much.
When I came out of the restroom, Sam asked if it any better and I shook my head no. He offered to take me to his office and get some club soda to try. I accepted and we walked around the corner to his office. I was very large and on the corner of the building. He grabbed a bottle of club soda and some paper towels and asked if he could help. I said yes and he dropped to a knee and tried to blot the stain with a little club soda. I thanked him for his efforts as the stain started to disappear. I asked what I could do to repay him for his efforts to save my dress.
He smiled and asked if I would go to dinner with him sometime. I smiled and said absolutely. He told me that he was a golfing buddy of Ben’s and Ben had mentioned that he was bringing a secret weapon to today’s meeting when they had played yesterday. I sensed this was my moment so I decided to go for it.
I told him that I thought that I should be able to repay the favor now if he was up for it. He got a sheepish grin on my face and I took that as a yes. I leaned forward and gave him a soft quick kiss and reached for his groin at the same time. His cock was already hard and felt like it must have been eight or nine inches long. I unzipped his pants and slid my hand inside. His boxers were silky and his cock was definitely longer than Ben’s.
I asked if this was okay for him, and he smiled and said he was loving it. I dropped to my knees and slid his pant down so that I could get a good look at his cock. It was definitely the longest one I had ever seen, but it wasn’t very thick. I told him that I had never seen one this long, but that I would do the best I could with it. I started kissing it, and then put it in my mouth. I worked my way down, but was only able to get about two-thirds of it down my throat. He placed his hands on my head to try and help me go further down. After about four or five minutes of this, I pulled off and motioned for him to sit on his couch.
He sat on the edge of the couch, and I asked him if I could ride him to get it all the way in. He said absolutely and thanked Ben for bringing me as his secret weapon. I reached up and pulled my panties to one side as I sat down on his cock. I was riding high and he tried to push me back a little, and I told him that I wanted him in my ass, and not my pussy. He beamed at that and let me slide up so that I could impale myself on his cock.
It took a few tries of wiggling back and forth, and then his head popped inside and I slid down. It took two of my up and down movements to get him buried in my ass completely. He moaned in pleasure and said that I had the best ass he ever had. He told me that we had to be quiet, but that he wanted to fuck me so bad all meeting and he was glad we were getting to do it so quickly. He commented that he loved my ass and I started to slowly slide up and down on his cock. After only about three minutes of that, he grabbed me tight and spurted load after load of come into my ass. We kissed deeply and he thanked me for doing him. I popped up off him, and bent down to lick him clean.
After cleaning him up good, I grabbed a paper towel and wiped the come that had started to leak from my ass. He got himself dressed and composed, and promised that we would got out for dinner again sometime. He said that he was looking forward to working with our team in the future, and that we can plan on getting the contract, if he had anything to do with it. I thanked him and told him that I would love to see him again.
He walked me back out and down to the lobby where Mike was waiting for me. He apologized to Mike for keeping me so long, but had asked me few additional questions about the project and my answers were very helpful in his understanding of what our team was bringing to the table. Mike thanked him and we left. As we walked to Mike’s car, he asked what really happened. I told him that Sam just had a few questions and I helped him with them.
We drove away and my phone began buzzing with text messages from Ben. I sent him a message that the project was going to be his and I would fill him in later when I was alone. He said okay, and promised that I call him later with the details. Mike started asking me out again and I decided to call his bluff. I reached over and began to feel his crotch.
Mike’s eyes went wide and he began to smile. He asked me if I was a prostitute hired by Ben to get this job. I told him that I might be, and would he be able to keep his mouth shut if I was. He said he kept lots of secrets, and I said that was good, because I am going to suck your cock while you drive us back to the office. I told him the longer he drove, the longer I would suck his cock. He agreed and almost immediately made a turn in a different direction. I unzipped his pants and freed his cock from his underwear. It was a medium sized cock, but very thick around.
I unbuckled my seat belt and turned and put my head in his lap. I began with little kiss to the top of the head of his cock. I then kissed around it and he moaned for more. I them took him in my mouth entirely and slowly went up and down on his shaft. He continued groaning and begged for me to go faster. I leaned up and told him if I went faster, that he would come quicker and I wanted this to last for a while.
I went back to the slow up and down motion with my mouth over his cock. His groans would get deep and then light as I went up and down. After what seemed like twenty minutes, my jaw began to get sore so I started going faster. In less than thirty seconds, he started to come and filled my throat with his load. I swallowed it all down and stayed on his cock until it deflated. As I lifted my head, I thanked him for the lunch snack. He thanked me for that and offered to have me work for him anytime. I told him that the first one was free, but after that, I was a twenty-five hundred per day escort.
He stammered that he couldn’t afford that much, but I asked if he liked my blow job. He said yes, and then agreed that it would be worth it, if he got to fuck me as well. I told him that I saved my pussy for my personal life, but that I would let my business partners fuck my ass as they chose. I told him that I had never had a cock as thick in my ass as his, but that if he wanted to try, I would be willing. He agreed that he wanted to try, but admitted that it would take him some time to get hard again. I told him that I could help with that as well.
I reached back down and started sucking his cock again. Soon it started to come to life. I told him to pull over to a secluded area, as I wanted to try and have him fit that fat cock in my ass. He soon pulled over in a rest area and led me into the woods behind the building. I found a tree that was about right for me and bent over it. I pulled my dress up enough for my ass to show and slid my panties to the side and said for him to try it. He pulled out his cock and pressed against my asshole. It was still a little wet from my previous session, and he started to press in. It was getting painful as his head was fighting his way into my sphincter. I tried to relax and then it popped it and went all the way it in one stroke.
I just about fell over from the pressure and pain, but the pain quickly subsided. I asked him to go slow and he had me fuller than I had ever been. He began to work in and out and soon it became more pleasurable for me as he was hitting my prostate. He only lasted a few minutes when he came again and filled my ass with his come. As he was filling my ass, the pressure put me over the edge and I came as well. He felt me spasm on his cock and was proud that he made me come from his ass fucking.
He said that was the first time that had ever happened to him, but that it was the first time a woman ever let him fuck there ass as well. I told him it was because he was so thick and that his cock was heavenly. He enjoyed the compliments and we quickly got re-arranged and went back to his car. We drove back to his office and he asked if he could write me a check. I told him that I only accepted cash, but that I would be by on Monday to pick up my envelope. He promised that he would have it ready, and I warned him that if he didn’t, I would have to tell Ben and he would make sure that Mike paid me. Mike asked me not to tell Ben, and I said that as long as he paid me, I would keep this our secret.
I gave Mike a kiss on the lips and then got out of his car in the parking lot at his office and walked to my car. I drove home and went in and relaxed on my couch. I texted Ben to call me and he did within fifteen minutes. I gave him the brief story about Sam, and told him that the contract was probably going to be his. He thanked me profusely and asked if I could come to his house that weekend. His wife wanted to get to know me better and he said that he needed to see me again soon.
I told him I would and that story is for later.
Erica
Hester
- 11.07.2022
- 15
- 0
- Category:
- Crossdressing
