This is a bit of an involved story. It is broken up into three sections. If you have the time you should start from the beginning. If you are a little pressed for time I suggest you jump to chapter three.

It must be difficult for a woman to work in a stereotypical male workplace. When I was 18, I was working in the repair department of a fairly large new car dealer in my home town. Between the repair shop, the body shop, sales, and customer service, there was not a single woman. There were only six women working there, and just as you may suspect, they all worked in either the clerical section, or at reception.
I would hate to call it a daily ritual, but since all of the employees park behind the shop, and the women all worked in the front, the would walk through the shop to and from their car each day. You could always tell when it happened too, because all of the air tools went silent, and the hoists would stop moving so the guys could take their time and stare at the ladies as they go through. I can’t say that I wasn’t guilty, but luckily for Margaret, there were two young blondes that would draw all of the attention.
Well, maybe not all of the attention. I had found out quite early that I fancy older women. Maybe it was the fact that their bodies tended to be naturally shaped closer to the proportions that I appreciate, or maybe it was that I had a bit if a mature nature myself, and was bored and annoyed with the normal attitudes of the girls I had grown up with. Whatever caused it, Margaret was the only one drawing my attention. And luckily, I believe that I was the only one at the time.
At 47, she was only petite in a few ways. She was 5’4” and was somewhat thin in the waist with nicely shaped legs. However she possessed an exceptionally round bottom, unbelievably wide hips, and a generous C cup that must have brought her to about 140 pounds, carried in all the right places. She always wore pants and a button down blouse, which would bulge just a little at her tight waistband. That bulge, combined with the wide hips and well proportioned breasts would make you certain of her not so recent maternity.
She had a cute face with soft features. Even without makeup, her natural beauty did not come close to showing her age. She wore round glasses over her warm, brown eyes surrounded be her shoulder length curled brown hair. I couldn’t have put together a more perfect mature woman if my life depended on it.
Yes, she was married, and had a son that I believe was just a few years younger than I. Obviously this ended my hopes of any relations, but that wouldn’t stop my cautious glances, randy thoughts, and the occasional flirting comment. I made an effort to be friendly with her when we crossed paths, and make conversation in the break room and any other chance I had. I would like to think it paid off, since I believe we were just a little closer than you would expect of two coworkers that are not even in the same section. It may have been enough to arouse suspicion from the other ladies, who loved to gossip of course, if the age difference had not prevented those thoughts to start with.
This continued for a few months. I began to make more flirtatious comments as I got more comfortable, and it seemed that she was more receptive to them, although she would never reciprocate. Then came the day that would change everything.
The clerical department always took their lunch early, so the break room would be less crowded. This also meant that I had never eaten lunch with Margaret. But today was different. My supervisor asked me if I was available for a job. He didn’t tell me what it was, but he said that it was scheduled for early this afternoon. I didn’t think anything of it, I just accepted the job, and he told me to break early so I could start during lunch.
I went up to the break room to take my lunch, and two of the ladies were already in there. One of the blonde girls was eating in the far back corner, watching the news. And Margaret was in the opposite corner reading a book, and looked to be finished with her lunch. I sat down across from her, and a seat over, because I assumed she didn’t want to chat. I opened my car magazine and started paging through while I ate.
Margaret looked over her book and asked me why I was there so early. I smiled and told her that I had planned to change my work schedule so I could look at her pretty face while I had lunch every day. She smiled and started to make small talk. We talked back and forth for a while, but something wasn’t right. I do not remember what I said, but at that point she seemed to get distant. I asked her what was wrong. She said it was nothing. I said “It is obviously something, come on, out with it.”
I didn’t expect what I heard next. She started to tell me that she and her husband had been having trouble. She said that her husband had an ongoing affair with some young bartender, and that they had actually been separated for a couple of months. I hadn’t expected her to confide in me and was a little surprised to hear that she had moved out and her son was staying with her husband. I tried to comfort her, but it didn’t seem like she was even really that upset about it. Then I looked up at the clock and saw that it was time to leave.
I stopped down by my bosses office to see what he needed me to do. He told me that they needed me up in the admin department to help with a little moving. This got me a little confused. I thought that Margaret would have known about it and mentioned this during lunch. But, nevertheless, I went upstairs to the admin department, and walked in to see Margaret standing there with a big smile on her face. This only added to my confusion.
“I told them I could use a young strapping man to help move some furniture. I figured they didn’t have too many to choose from.”
I kept sort of quiet, trying to gather what was going on around me. After I was done with what seemed to be an oddly small amount of work, Margaret asked me to come over and sit down by her desk. At this point, my confusion was turning into suspicion. I obviously wasn’t really needed to help with this work. Put that along with the odd events in the break room, something was going on.
Margaret cleared her throat. “OK, just give me a a while now, I have been noticing you,…. noticing me.”
Where was this going? Was this a harassment complaint? No, no, she was going somewhere with this. My mind started to race as I looked her in the eyes and she started to smile. I didn’t know what to do at that point. I looked down and cracked a smile.
I looked back up and started “I don’t know where cut me off.
“I’m just saying that we seem to get along well…..and with what I was telling you before…..I was wondering if you could do me a I guess not /> My mind came to a screeching halt and my face went blank. I am sure that it probably got pale too. Did I just hear that? Is she asking what I think,…no, hope, she is asking? It can’t be that in less than a hour, the opportunity that I figured would never come has not only appeared, but turned around and pounced on me! This can’t be happening! Calm down and say something!
“Sure, uh, sure, what, uh, what did you need?” I stammered.
“It isn’t really something I need, I guess it may be a case of bad timing. Like I said, right now I am separated, so that pretty much makes me single. And on Friday is my thirty year high school reunion. I know that it is not usually a big deal, but I do really want to attend, and the last thing I want to do is go stag. So I was hoping that you wouldn’t mind coming along and, I don’t know, sort of being my arm candy?
I am pretty sure my face went blank again. Really? Is that all she wanted? I guess it was my own fault for getting my hopes up, but I am sure it would have been a let down even if I wasn’t so excited.
“Yeah, that I said sarcastically.
She smiled and said “No, I am being serious. I would be the envy of all the old ladies if I strolled in with a young stud as my escort. And maybe I can make it worth your while…. I might have a few old friends with single /> “No thanks, I’ll be fine. But yeah, if you want me to I can go with you. It’s not a big deal. And I uh, might not be able to refuse, if you did want to make it worth my while.” I winked as I stood up to leave. I think I caught her off guard with that one. She lost her smile for a split second before she said:
“Great, if you could pick me up that would be terrific, and I will let you know when.”

Friday came, and I have to say that I wasn’t nervous, but the thought was in the back of my mind. Could I make something happen? I should have an opportunity if I play my cards right, but I shouldn’t get my hopes up. She is just doing this for the novelty of having a young guy escort her to the reunion, like it was senior prom again. I am sure the thought hasn’t even crossed her mind.
I was kind of excited though. My suit was just collecting dust in the closet, and I had just finished the restoration on my elegant Cadillac coupe, and tonight would be the perfect time to take it out. So I got dressed , got out her red corsage, and headed over to her apartment. I walked up to her door, and rang the bell, and when she came to the door, I almost hit the floor.
“Oh, you’re just in time. You can help zip me up.” She turned around and took a few steps back inside. My jaw dropped and I may have drooled. I stepped in and closed the door. I set down the corsage, and gently grasped the zipper and closed up the back of her dress. I could feel my pants getting tight as I took in this stunning sight. I was expecting her to be dressed elegantly, but I thought it would be a little more conservative.
She had on a set of black high heels and stockings, leading up into a flowing full length strapless satin black dress. I could see the one piece support she was wearing when I zipped her up, and it slimmed her waist to an even smaller size while adding what seemed like a full cup size. I did not expect her breasts to be in nearly full view either. I could actually hear my heart beating as I finally made my way to her face. She had decided not to wear her glasses, and she was wearing makeup for a change, which was probably the only conservative thing she was wearing if you didn’t count the voluptuous red lipstick.
She had her hair up and done quite nicely, and was wearing long black silk gloves to top it all off. If I didn’t know how hard she worked to get dressed up, I may have been tempted to get her to take it all back off right then.
“You look absolutely stunning, Margaret.” I finally said after what must have been a long, awkward silence. I honestly can’t remember.
“Thank you,” she said, “and you look very handsome. I truly will be the envy of all the ladies tonight.” She walked into the other room to get her purse, and I took the corsage out of it’s container. She came back in the room. “Oh, that is beautiful.” as I slipped it over her wrist. We then left for the reunion, which was being held at the ballroom of the oldest hotel in town.
The Cadillac had done it’s job, attracting an inordinate amount of attention as I pulled up to the valet in front of the hotel. I got out and met Margaret on the other side of the car as the valet opened her door. I took her arm, and she gave me a little peck on the cheek. “I really appreciate you coming.”
With that, I just smiled and we walked into the hotel. I planned to keep quiet for the event and just smile and shake hands. The ballroom was set up to what I assume their senior prom was supposed to have looked like. There was a brass band playing, as we walked in. We were fashionably late, so the room was full and there was a slow dance going, which turned out to be every other song for the whole night. We found our table and Margaret put down her purse, and then she took me around to say hi to all of her old, and current friends. She introduced me as her using the same tone every time as to suggest that we were involved.
After we had said hello to all her friends, we returned to our table with some drinks. We were seated with a couple of her friends who were high school sweethearts, and had been married shortly after school. I wasn’t terribly comfortable, and answered the usual questions of where I’m from and what I do, but stayed quiet otherwise. The couple was talking about how they were so happy to be able to recreate their senior prom, and the wife said they had planned to go up and get a hotel room to finish the night with authenticity. At that point, I was more than a little uncomfortable, and I just stared off as if looking at somebody on the other side of the room, so I could avoid eye contact for a moment. A few times, old boyfriends came over and asked Margaret for a dance.
“Do you mind?” Margaret asked.
“ Not at all.” I said. And really it did not matter, but I was actually a little jealous. I guess I was feeling a little possessive.
The event was ending at ten, and finally the reunion was over. The band announced the last dance. At that time a man that Margaret had pointed out before as being her last boyfriend before she met her husband came over and asked if she would do him the honor. She looked at me, and I nodded for her to accept, but she turned back to him.
“I’m terribly sorry David, but I had the last dance saved.”
He smiled weakly and walked away. Margaret turned to me and extended her hand.
“Now would you do me the honor?” She asked.
I took her hand and we walked onto the floor. We faced each other and as I took her other hand, I saw that she had a tear running down her cheek.
“I may not be the best dance partner, but you don’t need to cry about it.” I prodded.
She got a faint smile. “I couldn’t have hoped for a more perfect night.” She said as another tear came down her cheek and she put her head down on my shoulder. I couldn’t tell if she was just being sentimental, or if it was because she was enjoying herself in the moment. Then I had my answer as she let go of my hand and slid it down to join her other hand around my waist. She drew them around to my rear and pulled me in tight to press my groin into her. I think she was expecting to feel something press into her, but I have self control and I’m normally only stimulated when I am actually thinking about it.
The song ended and she lifted her head to give me another peck on the cheek. Then we turned to leave. We walked out of the hotel and I gave my ticket to the valet. He brought the car around and I opened the door for Margaret. We got in and I took her home. I am normally a quiet person, but I found it unsettling that she had said nothing for the entire trip.
We arrived at her home, and after I parked the car I saw her out of the corner of my eye. She was watching my hand to see if I would leave the car running or shut it off. It may have been my imagination, but I swear that she got a little smile when I turned it off and took out the key. I walked around and opened her door. I helped her out and closed the door. I took her arm and walked her to the front door. Once again I could hear my heartbeat and I wondered if I would have the courage to take my chances if the opportunity came.

We got to the front door and Margaret got out her key and unlocked it. When she went to put her key away I finally broke the silence.
“Well, despite the awkward situation, I did have a good time /> “I’m glad.” She said, “ And I just want to thank you again for doing this for me” And with that she leaned in to give me a goodnight kiss. I fully expected to get another peck on the cheek, but just in case there was any chance otherwise, I stayed centered and leaned in as well. I don’t know if she was aiming for my cheek before she closed her eyes, but she did just give a little peck, that landed square on my lips.
She slowly backed away and opened her eyes again. I looked straight into them, and when she started to come back in, I knew this was going to happen and we met in a heavy embrace . She put her hand on the back of my head, and I put my hands on her hips, and then slowly slid them around to her back and then down to her well shaped bottom.
I reached over and opened the door and we stumbled inside. I threw the door shut, and brought my arms around her back and she threw her arms around my neck. We kissed for a short time. She slid out her tongue and I massaged it with mine. Then, quite abruptly, she let go and broke the embrace. That was the moment I feared. She had second thoughts and was going to kick me out for sure.
She exclaimed. “No more romance, now I can thank you.” As she stepped back towards me, I recovered from my near heart attack and swept her up and off of her feet.
“Where to?” I asked.
“Down the hall. Last door on the right.” She cooed.
I carried her down the hall, with her arms around my neck again. I strode into the bedroom and set her down on the bed. She got back up, removing her gloves as I shed my jacket, and she took a firm grasp of my belt. As she was unbuckling my trousers, I reached around and slowly lowered the zipper of her dress. She took a step back and let the dress slide to the floor, once again revealing the lacy garment forming her body to a perfect ten. It had a firm hold below her chest, but was a transparent lace over her stomach, with a lace border curving over her hips and buttocks. It was also suspending her sheer stockings, with the straps underneath her panties.
Margaret stepped out of her dress and high heels as I stepped out of my shoes. She walked back to me and finished opening my pants as I unbuttoned my shirt. I slipped out of my shirt as my pants dropped, and I stepped out of them. At that point I expected her to go for my boxers, but instead she stood up and put her arms around me.
She pressed her face into my chest, and just stood still. Not knowing what to do at that point, I put my arms around her and held her for a moment. Finally she turned her head to the side.
“Six years.” She said. “I went without for six years until I finally found out that he was /> I let her gather herself for a bit while I wondered how any man could resist, let alone turn away this beautiful woman.
Finally she let go and reached to start lifting my undershirt. I grabbed it and finished taking it off before moving in to kiss her again. We continued for a moment before she drew her hands down my stomach and slid them underneath the waistband of my boxers. She slid them down enough to release my manhood, which was definitely ready to go at this point.
We continued to kiss while she stroked and fondled with both hands. I slowly rubbed my hands up and down her back and sides. I was enjoying myself, and was more than happy to let her set the pace. She broke off the kiss as she released me, and took my hand to lead me to the bed. I slid my boxers off the rest of the way with my free hand.
We started to kiss again at the side of the bed, as I leaned Margaret back without skipping a beat. I hovered over her, massaging her tongue with mine. Then I broke the embrace to begin my journey down. I lightly kissed her neck before moving to the top of the breasts one at a time.
I looked up to meet Margaret’s gaze as I drew my chin down across her lace covered stomach. I slipped my fingers under the sides of her panties and slowly slid them off of her legs. I drew my hands back up her legs and moved to her inner thighs. I overlooked her perfectly groomed pubic hair and used my thumbs to spread her lips.
Margaret closed her eyes and laid her head back. I started to rub her clitoris with a thumb and immediately found the sweet spot. I got up and knelt between her legs. Slowly rubbing her thigh with my free hand, and continuing to rub her clitoris with my thumb. I could feel her shudder when I would press up on it. I turned my hand and slid my middle finger into her vagina slowly. I stroked in and out slowly while I continued to rub with my thumb.
I am fairly confident in my stamina, but I wasn’t going to leave any chance of leaving her unsatisfied, therefore killing any chance of a repeat performance. I moved my free hand up to Margaret’s stomach, while I sped up my rhythm. She started to moan as I slipped in a second finger and bent them to push harder on the front of her love canal. I was amazed at how tight it was, let alone for a woman who had given birth.
She moaned louder as the energy seemed to crash over her in waves. Margaret’s moans turned to screams, and each time she did her stomach would tense, and she would squeeze down on my fingers. Every time I drew in, her juice would gush out onto my hand. I started to go a little faster. I arched my fingers a little more, and pressed a little harder with my thumb.
The screaming got louder, Margaret arched her back, and squeezed even harder. The screams faded into gasps and grunts, and she finally fell back to the bed, releasing her squeeze. Temporarily spent, she made no noise other that heavy breaths, but I could still make her tense when I pressed up on her clitoris. In an effort to show mercy, I withdrew my fingers and stood up from the bed.
I leaned over and slid my hands underneath her butt, pulling her to the edge of the bed. Spreading her legs, I went down to my knees to inhale the exceptionally sweet fragrance. I once again parted her lips and stuck out my tongue to taste the sweetness. I began to lap with my tongue flattened. I started at her opening and swept up across her clitoris.
She began moaning again, so I proceeded to insert two fingers again, this time rubbing the back of her canal. I began suckling and nibbling on Margaret’s love button as I stroked with my fingers. Almost immediately I was getting intense contractions, which told me that I had found Dr. Grafenburg.
Very quickly this time, Margaret had arched off of the bed, and was piercing the air with incessant screaming. With constant gushes and one last long cry, she collapsed once more. I withdrew once again, and proceeded to clean up, drinking in the sweet nectar without causing Margaret any more agony.
I backed out and stood up. After a moment catching her breath, Margaret tried to sit up, but it appeared her muscles were worn out to the point of failure. I took her hand and helped her up. Once on her feet, I quickly caught her as her legs gave out.
Holding her tightly she said “You really need to stop being so generous, now I have to pay you back for three good deeds.”
worry, I am sure you’ll find a way.” I said with a little laugh.
With that, she smiled and pushed me backwards onto the bed. I got settled in while she crawled up to me. All of that hard work had left me less than ready to go.
Margaret grasped me. “I should probably get started then.” She stroked a few times and proceeded to lick the head of my penis. I was to full strength in short order, and at that time Margaret began sliding down a good length of the shaft. I could feel myself hit the back of her throat, but that did not slow her down at all. She continued for a good ten minutes, but had no intention of finishing me off this way. She released me and got up on her knees.
“Are you tested?” She asked. All I could do was nod. “Good, because its not like I am going to get /> With that Margaret threw he leg over and straddled me. Holding the shaft, she guided me to her entrance and very slowly slid down. When she was all the way down, she spread her legs out as far as they would go to put all of her weight on me and take every inch. She leaned forward and put one hand down while reaching behind her back with the other. Lowering the zipper on her backside, she then reached down and removed the suspenders from her stockings.
Grasping the front of her garment, she ripped it of in a single motion, exposing her smooth white skin, perfectly shaped breasts, and very erect nipples. I swear I could have gone off right then, simply from the suspense. Margaret may have sensed this, because she just laid down, pressing her body against mine. She let out a bit of a sigh as she slipped her arms around me and was content to simply hug for the moment.
I slowly rubbed my hands up and down her back, grazing the sides of her breasts, and squeezing her nicely rounded bottom. After a few minutes, Margaret gave a little squeeze and started to lift up. She released her hold, came back down, and tightened back up before raising off again. She let go of her hug and sat up on me. I moved my hands to her hips as she started a rhythm. She had only started and already she was dripping down my shaft.
I was mesmerized at the beautiful breasts bouncing in front of me, and I could not believe how tight her grip was. I was in no danger yet so I let her set the pace. She would lean back and move short and fast, then lean forward and draw it out. Margaret stretched her legs out behind her and proceeded to grind her clitoris against my pelvis. I could feel her start to shudder again. After a few more strokes and a muffled scream, she collapsed on top of me.
Without separating, I rolled over into a missionary position and slowly brought Margaret back to life. Keeping that slow pace for ten minutes or so, I could tell that she was ready to finish. I leaned to the side and pulled her legs up to my shoulders one at a time. I folded her up as far a she could bend and proceeded to take my turn. Building up to a blinding pace, I would draw all of the way out and drive all of the way in.
Ready to finish at any moment, I relaxed as much as I could. Finally Margaret’s moans turned to screams once more. When she gave me her final death grip, it pushed in until I bottomed out, and released at least a dozen times deeply inside of her. I let her legs drop and stayed inside of her for a while.
I looked up to her eyes, just to see her with tears running down the sides of her face again. She smiled at me and gave me a little kiss. I rolled over and laid back, Margaret rolled to her side and draped her arm across my chest as we drifted off to sleep.

The next morning I woke up to the sunlight through the drapes. I got out of bed as Margaret slowly came around. I got dressed and she stood up, draping the bed sheet around her body. She walked with me to the front door, we shared a little kiss, and as I walked out she said:
“I think I still owe you. Next time you come over, you should park in the rear."

story by: slyde503

Tags: fiction mature romance male / older female older female / males sex story

Author: slyde503

Related sex stories: