Before I got married, I was working with an attorney in Dallas. I was his investigator. I wasn’t in the office very often, but would stop by a few times a week to get an expense check or pick up a few files. As usual, there were several girls that worked in there and they were always gossiping about something it seemed.
One Thursday afternoon, I stopped by the office around 4:30 and most everyone was packing up to head home. I wander around for a while and I start to head out when I see Mandy crying at her desk. Mandy is probably 30 years old but she’s the biggest girl of the group. I’d guess she was right at 200 lbs, maybe a little more. I walk over to her desk and ask if she’s ok. She seems startled and tries to act like nothing was wrong. It’s obvious she’s upset so I calm her down and sit down to show her I’m truly interested in what’s wrong. She finally tells me that she had a date planned with a guy tonight that she’d gone out with a few times, but he just called to cancel the date and said that he didn’t want to see her anymore. He gave her some bullshit about being too busy at work.
I stood up and told her to get her things, I was taking her to dinner. She tried to tell me that she’d be fine, but I wouldn’t take no for an answer. I tell her that I’ll drive and she comes out to my car. As I open the door for her, I find myself staring at her cleavage. Her tits were huge.
We drive to a steakhouse that’s near the office. As I keep listening to her story, I can see that she has no direction. I decide to help her and have some fun at the same time. As she gets out of the car, I let her catch me looking at the top of her tits. She blushes, not being used to attention. I let her step in front of me and slap at her big ass. She looks back at me shocked and then grins.
As we get in the restaurant, Mandy seems uncomfortable. I grab the back of her elbow to remind her that she’s with me tonight. She seems to calm down with my touch and we start walking to the table.
The waitress takes care of us with drinks and our order while Mandy continues to tell me her story. Finally, I’ve heard enough. I tell her that she hasn’t had a man in he life, just a bunch of insecure dicks that were trying to get laid. She looks at me with such a shocked face and then I tell her to go in the bathroom to take off her panties. She thinks it’s a joke but quickly sees that I’m serious and hurries off.
After too long, she comes back to the table with her panties in her fist. She seems scared to death. I reach out my hand and she looks around before finally handing them to me. They are damp, this must be getting to her. The bad part is that she was wearing these big cotton panties. And this was supposed to be a date night for her. Obviously, a lot of work to be done here.
Dinner arrives and we enjoy the meal, even though she seems very anxious. We finish dinner and I tell her that she’s spending the night at my house. She doesn’t really know how to respond, but just looks at the table. After I pay for dinner, we get back in the car and I start driving. She thinks we are going to my house but I pull into a shopping center. Before I get out, I ask her bra size. 40E. Wow, I knew they were huge. Her panties were XL so I headed into Soma. After a quick trip, I came back out with a bag. We drive home and she’s deathly quiet.
As we pull into my garage, I can tell she’s scared. I finally lean over to kiss her and tell her that it’s all going to be ok. I’m just going to help her learn some things about herself.
As we get in the house, I open a bottle of wine and hand her a glass. She quickly downs it, I guess trying to calm her nerves. I start walking to my bedroom and she follows. I sit down on an ottoman as she walks in. She seems caught, not knowing what to do next. I tell her to take off her clothes. She freezes and looks at the light. I realize that she’s probably been in the dark when with a guy. I nod at her to get her going and she finally starts unbuttoning her shirt. As her shirt hits the floor, she looks at her bra before unhooking it. As it falls off, her tits fall down to her navel. Not the best look, but she needs to get confident in it. I smile at her progress and she unzips her skirt. It takes some work to get it down as well as her pantyhose. She realizes that she’s fully naked and looks at the floor as she tries to cross her arms. I can see hair running down her thighs and up to her navel, terribly disappointing but not unexpected.
I call Mandy over to me.
“Look at yourself. This is your body”.
I let the silence sit while she looks over to the mirror.
“What do you think?”
Mandy “I’m fat and unattractive. It’s embarrassing to be naked in front of you.”
“I agree with parts of what you say, but a lot of it has been your choice, right? You don’t exercise, do you?”
She looks at the floor to answer.
“You don’t even take the time to buy attractive panties. You don’t even groom yourself, look at all of the hair. I’m sure it’s because you don’t think anyone wants to see you naked, but that’s no excuse.”
Mandy continues looking at the floor. I stand up and walk over to the bed and spread out a towel.
“Crawl up on the bed and lay on your back. Hang your legs over the side.” I hear her doing as told while I’m in the bathroom. I come back in the room with a bowl of warm water, shaving cream, razor and a towel.
“Relax, honey. We are going to pamper your pussy. It is very delicate and you are going to start treating it that way”.
Mandy “Yessir”
I lather her up and shave her a thin landing strip. I take my time wiping her up with the warm cloth and the drying everything.
“Lay here and touch yourself. Very softly. Here’s a mirror, you need to look at yourself.”
Mandy rolls over to get the mirror while I put up the shaving kit. I light candles and turn on music before I start bath water. I turn off the lights as I go back into the bedroom.
Mandy “it feels so soft, thank you”.
“We are only just getting started. I’m glad you like it so far though. Hop in the tub and just soak for a while. Close your eyes and just enjoy the music.”
Mandy “yessir”
As I hear her drop in the tub, I hop in the shower to rinse off after a long day. My dick isn’t hard but very solid. I get out of the shower and dry off but don’t bother with clothes. As I walk by the tub, I can tell that Mandy is touching herself until she sees me. Her eyes immediately go to my cock. I keep walking to the bedroom. I open the Soma bag and take Mandy a black bra and panty set. Mostly lace but some leopard print trim. As she gets out of the tub, she sees the panties and picks them up and just feels the soft fabric.
Finally, she walks in the bedroom and looks much better. She even has a smile.
“You look great! Do you feel better?”
Mandy “I haven’t felt this good in years. Thank you! These panties are so sexy, they look like what the other girls wear.”
“Well, you wear these now. We’ll go on a bigger shopping trip tomorrow but I’ve got enough to get you started. The rest of the night, we are going to work on your ability to serve and your confidence”
“How good are you at blowjobs?”
Mandy “I guess okay”
“Guess? Get up here. Get the head in your mouth and we are going to go very slow.”
Mandy crawls up in between my legs and grabs my cock. As she lowers her mouth, I look down to her tits and notice my dick harden up. She licks and teases the head and I raise my hips to get more in her mouth. Her eyes widen but she only takes it about halfway. Her inexperience is obvious. Guys have used her mouth but she’s not given much head. I put my hands behind her head and pull down. She struggles but I don’t let go, she has to learn to please her man. As she coughs and starts to spit, I let her back off.
” honey, you have to relax and breathe through your nose. All of this dick is going in your mouth, one way or another”
Mandy goes back down and is pushing herself. I wrap my fingers behind her head again. I let her work herself but start pulling her down. Her eyes are watering and she’s gagging/coughing. I finally get all of it in her mouth. She’s struggling less now. She then starts going down on her own. I lean back seeing that she’s doing better now. I’m fully hard and feel my dick on the back of her throat. I start enjoying the blowjob and Mandy starts sucking harder. This goes on for a while and she’s definitely getting comfortable at what she’s doing. I lean up and pull her head so that my cock is all of the way in her and look into her eyes as I feel the cum running up my dick. Mandy tries to pull back but I hold her tight. I see the cum trying to come out of her mouth but she’s able to hold it. Damn, it felt good.
I pull Mandy up to me as I lean back. She leans in to my face so I finally get to suck on her huge tits.
“You’re a good cocksucker, Mandy. You’ll get better but that was great.”
Mandy “thank you sir”
“Thank you, daddy”
Mandy “I’m sorry. Thank you, daddy”.
“Crawl up on the bed and lay back, I want to eat your pretty pussy.”
Mandy “no, you don’t have to. It’s ok.”
” I didn’t ask. I’m going to eat you. Don’t worry, I think it’s beautiful! ”
As I moved down, she tenses up and I start kissing her thighs. As I get to the crease of her thigh and pussy, she lets out a deep moan. I can feel the heat from her pussy. I take long slow strokes up and down her pussy. It would be easy to get her off but I keep it slow and back away if she gets too close. After quite a bit of teasing, I slip two fingers in her and start pulling on her gspot. I keep licking her clit and she leans up and starts shaking. This is a full body orgasm. She’s gushing and bucking against my hand as she rides out the orgasm. I don’t remember a girl ever losing control like Mandy while I ate them. Mandy laid back breathing so heavy.
Mandy “Oh daddy, I’ve never felt anything like that. I felt that all over my body. Nobody has ever worked to make me feel good like you.”
“I’m glad you enjoyed it, babygirl. Your pussy tasted so good. Now crawl up on me. We need to make sure you can ride my dick.”
Mandy “no, I don’t want to do that. I’m too big. Most guys just bend me over and fuck me. Let’s do that.”
No sooner than she stopped talking, I slapped her ass several times real fast.
“I didnt ask, dammit. You do what you’re told. Now. Your job is to please your man.”
Mandy crawls up in my lap. Her belly was in the way and it wasn’t easy for her to move around but that’s her problem. As she throws a leg over my thighs, I slap her clit with my dick. She squeals and rubs the head along her pussy. She’s so wet, I slip right in. She works herself up and down a few times before getting it all in. I immediately grab her hips and start thrusting up in her. She’s very awkward as she tries to ride me but gets smoother. Mandy leans forwards and grinds her clit to a quick orgasm. This helps her relax and she starts grinding harder.
Mandy “please daddy, fuck me harder. It’s your pussy. Fuck it and make it feel good.”
Like everyone, she gets real honest right before she cums. I raise up and just start pounding into her from below. She loses control and cums much harder this time.
Mandy “cum in me. Mark me. Shoot it all in me. I just want to feel your hot cum.”
I pull Mandy down to me and start sucking on her tits just as I feel my cum start pumping in her. Each shot feels huge coming out. She loves it and does her best effort at slamming herself up and down on me.
I lay back, exhausted. Fucking this big girl was a workout. I pull Mandy down beside me as we catch our breath. Both of us sweaty and still breathing hard, but it felt nice.
“Honey, you did really good tonight. I enjoyed myself, but I also enjoyed seeing you pick up some confidence. I’m going to offer you to spend a month here with me and give me control of your life. You need it. If you don’t get back on track, you’ll be miserable the rest of your life.”
Mandy ” what would I do while I’m here?”
“Whatever I tell you to do. That simple. And when you don’t, there will be punishment.”
Mandy “Yessir, I want to try it.”
“Ok. Go put on those panties and I’ll give you a tshirt. No bra tonight I guess. You’re going to walk on the treadmill for an hour before bed. You shouldn’t try to be skinny like one of those Barbie doll girls, but you are going to get in better shape.”
Mandy “yessir. I mean yes daddy”
As we walk through the kitchen, I make her get a big jug of water. She has to drink a gallon every day. I pull out a bucket from under the sink. I tell her that’s where she pees when at home until she loses 5 lbs. She looks at me in shock but nods. As we walk over to my treadmill, I start it for her.
“One hour, not a minute less. If you get off to pee, pause it until you come back.”
Mandy “Yes daddy. Don’t make it go too fast, your cum is pouring out of me.”
“You’ll do fine.”
Mandy gets on the treadmill and starts walking. I go back to the bedroom to clean up. This is going to be an interesting month.
Source: reddit.com/r/sexystories/comments/5dy1qa/firm_with_a_friend