Note: This story was dynamically reformatted for online reading convenience. This site contains fictional stories with explicit descriptions of sexual activities, and not suitable for minors or prudes. If you are under 18 year of age, do not enter this site as it is illegal for you to do so and you are not welcome here. Also if you are offended by sexually explicit stories, do not enter this site, as I do not wish to offend your sensibilities. Having said that, by entering this site you are representing that you are at least 18 years old and do so of your own free will and are not offended in any way by sexually explicit stories. The stories are fictional and any resemblance to actual people or other entities is purely coincidental. ======================================================== Jan is a delightful lady, who had and probably still has zero self-esteem. I met her on line one evening in a chat room and then contacted her directly the following night for some one on one chat. It turns out that Jan is a divorced mother of 2 adult children and for whatever reason hasn't been intimate with anyone for close to 5 years (according to her). After a series of chats over time, Jan accepted my invitation to meet and end her 5 years dry spell. The agreement was that in order for her to get over her shyness, I'd guide her as if she was in an interview. This is something that I really enjoy and look forward to doing with any lady. The time arrived and I heard Jan knocking on the hotel room door. I opened the door and invited her in. Nervous, she stepped in glancing around and wanting to be certain she was in the right place and going to be okay. Please, look around, make yourself at home, I said. Jan glanced around, then walked into and out of the bathroom. Here, I said, have a seat, tapping the sofa. Jan, smoothed her skirt and took a seat. Have any problems getting here, I began? No, no not really...you know, just the usual traffic, she said. So, tell me a little about you, I said. What would you like to know, she asked. Lets begin with who you are and what you do, I suggested. Well, she began taking a deep breath, I'm Jan and I'm 49yrs old, divorced and have adult children, even a grandchild on the way. That's wonderful, I replied, congrats. I work at a very unusual job for a woman, in that I repair and maintain equipment. Wow, that's neat, I said. Yes, but certainly I'm not out all dressed up pretty to meet anyone. Guess that's the drawback, she added. So how long have you been alone, I asked. Almost 5 years, she replied. That's quite awhile, I said then added, so you think that this job will change some things for you? Yes, hopefully, she said. You know what we're here for don't you? Yes, I believe so, she replied. Well, just to be certain, let go over it, I said. We're interviewing ladies such as yourself to appear in an adult film. It will require you following directions as well as contributing to the role as this is a partnership effort. I understand, she replied. Lets get started then, I said, how about you stand up and walk around the room some so I can get a good look at you. Jan stood, looked around for a second or two, then walked to the other side of the room, turned and returned to stand in front of me. I didn't say anything, but just sat and looked at her. I'm too fat, aren't I, she said. No no, think you're just right, I said, just wondering about a shorter skirt. Lift you skirt a little, I said. Jan gathered her skirt and inched it up over her knees. Little more, I said. Thats good, now try to hold that length and sit down. Jan carefully held onto the skirt and looked carefully before taking a seat. I looked at how the skirt had ridden up some, then moved in front of her and looked up her skirt. Open your leg just a little, I said. Jan waited a second or two, then slowly parted her legs allowing me to gaze all the way to her panties. Okay, I said, now let stand again. Jan lost the hold on the skirt, but I told her to ignore it and turn sideways for me. I moved along side her and asked what size dress she wore. A 16/18 depending on the cut she said. Okay, I said, now slowly take off the dress and then hang it in the closet. Jan reached over her head and unhooked the top of the dress. Then twisting her arms behind her, reached for the zipper and pulled it down. Next she reached for a shoulder and slipped the fabric down her arm slightly exposing one cup of her bra, then the other thus fully exposing her bra. She then pushed the dress over her hips and held the top as it fell to the ground where she stepped out of it, then lifted it and moved across the room to the closet where she hung the dress. Now in just her bra, panties and heel she walked back to stand before me. I could see she was a bit nervous, but there was nothing I could do about that. Turn around I said. Jan turned her back to me and stood there. Pull the back of your panties down so I can see those cheeks, I said. She reached for the waist band and pulled the back of her panty down so I could see the dimples of her ass. Satisfied I told her to turn around. A somewhat red faced Jan now stood before me arms at her side. Tell me about your tits, I said. What about them, she asked? You like them played with, sucked on? Oh, I enjoy it all, she said. What size are you, I asked. 38D was the reply. Been awhile since you've been seen like, I asked? Yes, she whispered. Nervous, I asked? Yes, very, she replied. Lean forward, I said. Jan bent forward and I was able to see her tits hanging within the cups of her bra. Push those straps down, I said. Jan slowly moved a hand up to her shoulder and pulled the strap off, then the other strap. Thats better, I said, now I can just about see your nipples. Think I'll like your nipples, I asked? I hope so, said Jan. Really, I said then added, why don't you unhook your bra then and show me your tits? Jan straightened up and reached behind to unhook the bra. Unhooked, she continued to hold it against her as she stood before me. I hope you won't be disappointed she said, as she slowly released her hold on the bra and it fell away revealing her full sized tits to me. Now why would I be disappointed, I asked? I guess, I'm just not as firm or well you know, she said. Really don't know, but lets find out...put your bra back on, I said. Jan picked up her bra and put it back on. Comfortable, I asked. Yes, oh you mean, she said. Yes, tits cozy, I asked? Jan cupped herself and in a few seconds pushed the meaty globes so they were well housed in the bra. Okay, get down on your hands and knees, I said. Jan lower herself to the floor and then on all fours looked up at me. I looked around the room and finally tore the cover off the phone book. I held it along side her tit and marked on the heavy paper how far she hung down. I then extended my hand and helped her up, noticing that her still half off panty was giving her a bit of difficulty, but chose to ignore it. I then stepped to her and began to feel her tits locating her nipples inside the bra. Like your tits being felt, I asked? Yes, she replied. I then pulled her towards a wall where I put a hash mark on the wall indicating the location of her nipples. Now take off the bra, I said. Once again Jan removed her bra and I moved her to the wall where I easily marked where her nipples were now located. Now, get back down on your hands and knees, I said. I picked up the paper and again placed it against Jan and marked the length that her tits hung beneath her. I took a minute to play with her larger hangers, and then moved behind her, and spread her legs apart. Like doggie style, I asked. Sometimes, said Jan, if you want me that way, it's okay. But, its been awhile for you, hasn't it, I asked? Yes, afraid so, she said, but jumped a little as I slid my hand between her legs and inside the folds of her panties. Pussy's a little moist, isn't it, I said getting no reply. Here, I said extending my hand once again to her so she could stand up. Take off the panties, I said. Now, questioned Jan? Yes, right now, I said. Jan moved her hands to her waist, totally ignoring that she was topless and grasped the front of her panties and pushed them down. Once they were at the same level as the back side, they were free to fall to the floor where Jan slowly stepped out of them. You're very pretty, I said looking down at her slit. Thank you, she politely and somewhat embrassingly said. Sit down I said, motioning her to an arm chair. Jan sat down and naturally crossed her legs obscuring any view of her naked pussy. Play with your tits, I said. A very questioning look came over her face and she started to say something, but then didn't, yet moved her hands to her chest and slowly started to fondle herself. Open your legs, I said. Slowly Jan uncrossed and opened her legs allowing me to see her pussy. It excite you, my seeing your pussy, I asked? Jan didn't reply, so I continued. I want you to drape your legs over the arm rests. Jan looked, no stared, at me then tried to lift and move one leg, but finally moved her her hands and lifted each leg and draped them over the arm rests of the chair. Now with her legs spread wide open and fully exposed, I moved her hands back to her chest, then knelt in front of the chair and using one finger began to move along her inner thighs circling ever so closely to open pussy. Finally I ran my finger along her pussy's lips and teased her clit with my touch. Jan moaned and asked me to please fuck her. Few things first, I said as I slipped my thumb into her and pushed against her "G" spot. Yes, anything she sort of gasped, Play with this, I said handing her a dildo. Jan looked at me, then the dildo before she took it from me and began to rub it against her clit and back and forth through her slit. Then she slowly slipped the head into her swollen pussy and was soon pumping like she was drilling for oil. I moved to her and pushed her hands away, then grabbing the dildo began to use it on her myself along with starting to work my lips and tongue on her clit. Jan, started moaning and trashing about in the chair, but there wasn't much room for her to move about without falling.