Straight Male / 38
Sexy Associate, The Big Time
So now this is me turning my cute little office girl into my own little slut. After our first two encounters, I went crazy thinking about what I could do to top everything. Lauren’s not completely willing, but willing enough. After what happens in here, I seriously plan to settle down and just get some casual sex in with her and calm things down so she doesn’t freak or get too uncomfortable. Again, if you don’t like what I have to say or can’t believe it, don’t read. This is for me to confess and relive it “out loud”.
I didn’t leave Lauren rest long and on Friday I called her in my office again. She had on leggings and a comfortable sweater and had been casual dress on Thursday too. After she closed (and locked…) the door, she said “I’m sorry, I just really needed to dress down today.” I said “That’s okay, don’t worry. That’s not what I was thinking about. Take a seat.” She sat semi-casually in her seat as I finished some work. She didn’t look nervous for once, as she was getting used to things.
“I have a proposal I need you to think about.” I said. I explained my plans. We would drive up to the other office our company had a few hours away. I’d pick her up at her house and could even say hello to her husband. We’d leave on an evening when her husband would be home from work. She grimaced when I suggested the hello but kept listening. We’d drive out of town and then make a stop where I would give her a special outfit. It would be very sexy. She should bring a jacket to cover up in. Some of the areas we’re driving through are a little seedy.
“Have you ever been to an adult book store with a theater or movie room?” I asked. “No, never.” She said. I asked her really no and she said really no. I explained the outfit would be for the adult book store. There are a couple along the way and we would stop at a good one I knew. I have been to some of them, but only to browse and to buy something for my wife, but I knew what could happen in there, especially at this one. Then I asked her “Ok, now be serious with me, would you have sex with other men?” I asked in plural. She stiffened in her chair, “No, I’ve never done that!” “I didn’t ask that” I said “Are you willing to have sex with other men for me to be your advocate?” That’s how decided I’d phrase it. “I don’t think so…” she trailed off quietly. “Ok,” I said, “just curious. That’s all I needed to know.” Lauren sat for a second, “Wait, what does this me for my job?” “Nothing,” I replied, “but I’m trying to be your advocate and that’s up to you.” “Would you fire me?” she asks nervously. “No, not over that.” I said, “But, you need to be really careful about your errors.” Her shoulders drooped instantly. “You seem to feel good during our little sessions, right?” I asked. “I…I…I don’t know…” she stammered trying to think. “You go home and think what you want to do, it’s your call.” I said. She stared down at the desk again, then looked at me and said, “No, it’s ok, I’ll go.”
Tuesday evening this past week came and I told her I would pick her up after work so she had time to go home and get ready. We could have left from the office, but I wanted to meet the husband. I got to their little townhouse and rang the doorbell. Her husband opens the door and we meet for the first time. He’s a nice looking guy, similar or maybe slightly smaller build than me. He’s very polite. He’s an assistance manager at some fast food restaurant but I don’t remember which…who cares? “Lauren” he calls to the stairway. Down comes Lauren, just as cute as always, dressed in a sweater, skinny jeans and a pair of flats. She has her overnight bag, a medium length camel color raincoat and her purse. That would change soon enough. “Ready to go?” I asked. Lauren stopped by her husband as he leaned in to kiss her. They gave a quick peck and “I love you” and we headed to the car to load the trunk.
I got Lauren to talk in the car…more than a few sentences. We talked current events of which she knew some but mostly as if she reads People or watches E! on tv. We got further out of town and I said, “time to pull over.” We get to the rest stop I had in mind. At the trunk, she gets out her jacket and I give her a black bag with her new outfit. I bought it online, had to overnight it to be sure it arrived early enough, and had to be careful my wife didn’t open it first. Lauren said, “Ok, I’ll go change.” I call out as she leaves, “don’t wear anything you have on, only what’s in the bag.” She’s in the restroom for a few minutes, not forever, but I’m sure long enough to be worrying about her new outfit. She comes out with her regular clothes in the black bag and her raincoat closed tight. The only difference is that instead of flats she has on a pair of 4 inch platform heels with red soles and the shoes are probably a half size big. Oops. “Do you still want to do this?” I ask. She gives a short reluctant laugh, very nervous and says, “Let’s go.”
Beside some really meaningless small banter to pass the time and pretend there wasn’t tension we did have one frank conversation before we got in the book store. I asked her, “Did you get birth control?” She replies, “No not yet, but I made an appointment.” I replied “Holy shit Lauren, this isn’t going to work.” She sat quiet, then said “I get my next period in like five days, maybe seven. My husband and I try to keep track and he pulls out.” My immediate comeback, “He doesn’t cum in you?” “No”, she replies, “he always goes on my belly.” I say, “Damnit Lauren, this ruins it.” She starts to panic in silence a little, I can sort of tell, then she says, “I don’t think it’ll happen and my period is coming soon. I should be okay.” “Are you sure?” I ask and she replies, “Yes, it’ll be okay. We go a few more minutes in silence, then I ask, “did he ever cum in your ass?” knowing I had just done that two days ago. “No,” she says, “he always pulls out and comes on me somewhere else.”
We get to the book store and I park to the side near one of the few lights. There’s a truck stop across the street and even now there were two truckers walking across to the book store. The store is just a cement block building with a small sign saying “XXX Books and Movies”. I look at her and put a hand on her arm lightly. “The coat stays in the car.” I say. She exhales and says “Oh, God.” We get out of the car and she takes of her coat and throws it on her seat. I come around the car to stand a few feet away and take her in. Lauren looks a little like Selena Gomez like I said, maybe even better and has a hot body. Her hair is down to her shoulders, straight and lightly parted on the left side. The outfit is fantastic. Her perky chest is covered by a little black tube top that just covers her boobs. Her midriff and flat stomach are exposed. The skirt is fake leather and measures 8 inches long, just covering her crotch where her legs meet but nothing more and probably less when she moves. I motion for her to turn around and she does, still looking down. The skirt hangs on her hips, but it’s not enough to cover all of her ass cheeks. It has slits on the sides that are two inches high and are already stretch with how tight the outfit is. Maybe an inch or so of cheek poke out the bottom as she stands still. Her legs are amazing and stand out in the 4 inch heels. “Ready?” I ask, and motion for her to walk in front of me to the door. As she walks I see the slits allow the back of the skirt to pull up so that the back panel is maybe 5 or six inches of coverage. She basically moons me.
We get inside and the few guys in the retail area basically stop and stare as Lauren walks in. We go directly to the main desk with bullet proof glass and I lean down to speak through the glass. “Are we okay to go in?” I ask. The guy looks at Lauren and scans her several times to take her in. “Fuck yeah!” he goes, “But do you want to?” He was talking to me but Lauren leans slightly over and says “Yes.” matter-of-factly into the glass. As she leaned over, I heard a guy behind her go “Wow.”
I will post the rest next.
I didn’t leave Lauren rest long and on Friday I called her in my office again. She had on leggings and a comfortable sweater and had been casual dress on Thursday too. After she closed (and locked…) the door, she said “I’m sorry, I just really needed to dress down today.” I said “That’s okay, don’t worry. That’s not what I was thinking about. Take a seat.” She sat semi-casually in her seat as I finished some work. She didn’t look nervous for once, as she was getting used to things.
“I have a proposal I need you to think about.” I said. I explained my plans. We would drive up to the other office our company had a few hours away. I’d pick her up at her house and could even say hello to her husband. We’d leave on an evening when her husband would be home from work. She grimaced when I suggested the hello but kept listening. We’d drive out of town and then make a stop where I would give her a special outfit. It would be very sexy. She should bring a jacket to cover up in. Some of the areas we’re driving through are a little seedy.
“Have you ever been to an adult book store with a theater or movie room?” I asked. “No, never.” She said. I asked her really no and she said really no. I explained the outfit would be for the adult book store. There are a couple along the way and we would stop at a good one I knew. I have been to some of them, but only to browse and to buy something for my wife, but I knew what could happen in there, especially at this one. Then I asked her “Ok, now be serious with me, would you have sex with other men?” I asked in plural. She stiffened in her chair, “No, I’ve never done that!” “I didn’t ask that” I said “Are you willing to have sex with other men for me to be your advocate?” That’s how decided I’d phrase it. “I don’t think so…” she trailed off quietly. “Ok,” I said, “just curious. That’s all I needed to know.” Lauren sat for a second, “Wait, what does this me for my job?” “Nothing,” I replied, “but I’m trying to be your advocate and that’s up to you.” “Would you fire me?” she asks nervously. “No, not over that.” I said, “But, you need to be really careful about your errors.” Her shoulders drooped instantly. “You seem to feel good during our little sessions, right?” I asked. “I…I…I don’t know…” she stammered trying to think. “You go home and think what you want to do, it’s your call.” I said. She stared down at the desk again, then looked at me and said, “No, it’s ok, I’ll go.”
Tuesday evening this past week came and I told her I would pick her up after work so she had time to go home and get ready. We could have left from the office, but I wanted to meet the husband. I got to their little townhouse and rang the doorbell. Her husband opens the door and we meet for the first time. He’s a nice looking guy, similar or maybe slightly smaller build than me. He’s very polite. He’s an assistance manager at some fast food restaurant but I don’t remember which…who cares? “Lauren” he calls to the stairway. Down comes Lauren, just as cute as always, dressed in a sweater, skinny jeans and a pair of flats. She has her overnight bag, a medium length camel color raincoat and her purse. That would change soon enough. “Ready to go?” I asked. Lauren stopped by her husband as he leaned in to kiss her. They gave a quick peck and “I love you” and we headed to the car to load the trunk.
I got Lauren to talk in the car…more than a few sentences. We talked current events of which she knew some but mostly as if she reads People or watches E! on tv. We got further out of town and I said, “time to pull over.” We get to the rest stop I had in mind. At the trunk, she gets out her jacket and I give her a black bag with her new outfit. I bought it online, had to overnight it to be sure it arrived early enough, and had to be careful my wife didn’t open it first. Lauren said, “Ok, I’ll go change.” I call out as she leaves, “don’t wear anything you have on, only what’s in the bag.” She’s in the restroom for a few minutes, not forever, but I’m sure long enough to be worrying about her new outfit. She comes out with her regular clothes in the black bag and her raincoat closed tight. The only difference is that instead of flats she has on a pair of 4 inch platform heels with red soles and the shoes are probably a half size big. Oops. “Do you still want to do this?” I ask. She gives a short reluctant laugh, very nervous and says, “Let’s go.”
Beside some really meaningless small banter to pass the time and pretend there wasn’t tension we did have one frank conversation before we got in the book store. I asked her, “Did you get birth control?” She replies, “No not yet, but I made an appointment.” I replied “Holy shit Lauren, this isn’t going to work.” She sat quiet, then said “I get my next period in like five days, maybe seven. My husband and I try to keep track and he pulls out.” My immediate comeback, “He doesn’t cum in you?” “No”, she replies, “he always goes on my belly.” I say, “Damnit Lauren, this ruins it.” She starts to panic in silence a little, I can sort of tell, then she says, “I don’t think it’ll happen and my period is coming soon. I should be okay.” “Are you sure?” I ask and she replies, “Yes, it’ll be okay. We go a few more minutes in silence, then I ask, “did he ever cum in your ass?” knowing I had just done that two days ago. “No,” she says, “he always pulls out and comes on me somewhere else.”
We get to the book store and I park to the side near one of the few lights. There’s a truck stop across the street and even now there were two truckers walking across to the book store. The store is just a cement block building with a small sign saying “XXX Books and Movies”. I look at her and put a hand on her arm lightly. “The coat stays in the car.” I say. She exhales and says “Oh, God.” We get out of the car and she takes of her coat and throws it on her seat. I come around the car to stand a few feet away and take her in. Lauren looks a little like Selena Gomez like I said, maybe even better and has a hot body. Her hair is down to her shoulders, straight and lightly parted on the left side. The outfit is fantastic. Her perky chest is covered by a little black tube top that just covers her boobs. Her midriff and flat stomach are exposed. The skirt is fake leather and measures 8 inches long, just covering her crotch where her legs meet but nothing more and probably less when she moves. I motion for her to turn around and she does, still looking down. The skirt hangs on her hips, but it’s not enough to cover all of her ass cheeks. It has slits on the sides that are two inches high and are already stretch with how tight the outfit is. Maybe an inch or so of cheek poke out the bottom as she stands still. Her legs are amazing and stand out in the 4 inch heels. “Ready?” I ask, and motion for her to walk in front of me to the door. As she walks I see the slits allow the back of the skirt to pull up so that the back panel is maybe 5 or six inches of coverage. She basically moons me.
We get inside and the few guys in the retail area basically stop and stare as Lauren walks in. We go directly to the main desk with bullet proof glass and I lean down to speak through the glass. “Are we okay to go in?” I ask. The guy looks at Lauren and scans her several times to take her in. “Fuck yeah!” he goes, “But do you want to?” He was talking to me but Lauren leans slightly over and says “Yes.” matter-of-factly into the glass. As she leaned over, I heard a guy behind her go “Wow.”
I will post the rest next.
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