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Son's Best Friend Wants Me


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Becoming a MILF

I have decided to tell my story on behalf of any women who find themselves in a similar situation.

My husband and I had been married for over twenty years and had a comfortable life. My daughter was married and living abroad and my son was still living at home.

My suspicions that all was not well were aroused by my husband's sudden lack of sex drive. He was becoming more remote and there was an increase in late night working at the office. Eventually, it all came out, he was having an affair with a work colleague who was much younger and single. To cut a long story short we divorced, I kept the house and got myself a job. That was about five years ago.

This year I hit fifty, still single and living a life consisting of work and home life. My son Jon and his long-standing friend Phil organized a birthday party for me which was great fun and I was very appreciative.

I've developed a close relationship with a work colleague Karen. Karen is ten years younger than me and completely different. She is also divorced but very attractive and young at heart. Karen has a very active social life and is regularly dating and sleeping with younger guys. Her stories are very interesting.

One day I was in the house cleaning with the windows open. Jon and Phil were outside relaxing and talking. I couldn't help but overhear the conversation.

Jon was talking about his forthcoming holiday with his girlfriend and how he was looking forward to regular sex. He was having a go at Phil for his lack of a girlfriend. It seemed that Phil preferred older women but had failed to get a date with an older barmaid at the local pub. Phil was defending himself and saying how sexy some older women could look.

He suddenly said how attractive I had looked at the party and he was amazed I didn't have a man in my life. He said I came from an era when women dressed to look attractive to men, looking sexy and even wearing stockings and suspenders. He went on to say how he would love to sleep with me if the opportunity arose. You can imagine Jon's scorn.

I was shocked to hear this as I had known Phil since junior school and looked upon him almost as a son.

The next day Karen came around for coffee and the latest update on her exploits. When she stopped talking, I told her about what I had overheard. Karen's reaction surprised me.

Karen said I should think seriously about how I could make the situation work for me. I said that was ridiculous as Phil was Jon's best friend and half my age. Karen said the sex story websites were full of stories where older women had sex with their son's best friends and showed me some. She said I should think seriously about getting a sex life - reminding me it was over five years since I last had sex with my husband.

Karen said I could put any conditions I wanted to on a relationship, and it sounded as if Phil would be very keen to comply. I said it was ridiculous to think of such an affair with someone I had known since he was at junior school and then there was STDs to worry about. Karen responded that I could insist on the use of a condom as she did and I should give this situation some thought.

That night I lay in bed thinking about the situation, privately feeling a compliment that a younger guy found me attractive but still rejecting an affair as completely ridiculous. I drifted off to sleep but awoke later to find myself thinking about sex and I was very sexually aroused. I had to reach for my vibrator and I soon had the most intense orgasm I could remember.

A few days later Karen arrived for coffee again and this time the first thing she wanted to talk about was me getting Phil into the sack. I still needed convincing, but Karen played the great sex card well, stressing that once I had sex with a young guy, I would realize what I had been missing. For my part, I kept thinking back to last night's orgasm which made me realize what I was missing.

Karen reiterated that I had complete control of the situation as Phil wanted to sleep with me and I could put any conditions I wanted on the deal. The point was well made and I decided it was time for some 'me time'.

By this time my son was away on his holiday, so arrangements were made for Karen to pick me up that night and drive me to the pub we knew Phil and friends frequented on a Friday night. I was still feeling some reluctance although by now more than a little intrigued. I dressed conservatively in a patterned blouse, black trousers, and black heeled shoes, hardly likely to catch the eye.

At the pub we bought a drink and then Karen walked over to Phil, dragging me behind and started talking to Phil. He was surprised to see me. Karen said I was all on my own as Jon was away on holiday.

We all made small talk for a while and then Karen announced that she had a date and had to go. This was unexpected and I protested that she was my lift home. Karen turned to Phil and said she was sure he would ensure I got home safely to which he said he was designated driver and did have a spare seat.

With that Karen was gone and I was stood with Phil. I felt a little embarrassed, but he was great. He bought me another large glass of wine and suggested we sit down in a quiet corner. He was really good at making small talk, but we did know each other well. He seemed really pleased to spend time alone with me which fitted in with my hopes and aspirations. I noticed that Phil kept focussing on my cleavage.

As the evening drew to a close Phil said that as we were both at a loose end the following night how about if he took me out for a meal? I liked the sound of that but was a little afraid I might bump into a work colleague, so I made an excuse.

I could see he was disappointed, so I suggested that it was more appropriate if I cooked a meal for the two of us at my place and that he bring a nice bottle of wine. He liked that idea. I suggested that it would be better if he didn't mention it to anyone.

He drove me home with another couple in the back of the car who appeared to be making out. I could see the guy had his hand up the dress of the woman and she wasn’t objecting. He dropped me at my house and drove off when I was safely inside. I excitedly sent a text to Karen telling her what had been arranged and almost immediately I received a response saying she was taking me shopping for sexy clothes early the next day.

That night I thought about my approach to the evening. I wanted Phil to see that I had made a special effort and even dress a little provocatively to give him a come on. I thought about a short sexy dress and leg show but thought back to his comment about me coming from the era of stockings and suspenders and decided that I would wear them for him. My current underwear was functional rather than sexy, so Karen's input was necessary.

Karen was so excited at the prospect and we spent a fun-filled morning shopping. She said I needed some sexy lingerie and she was thrilled at the prospect of stockings and suspenders.

I bought a lacy black bra, lacy thong panties in black, skimpy black suspender belt and a pair of fully fashioned point heeled black nylon seamed stockings.  In my experience, any man seeing seams would realize a woman was wearing stockings.

I tried on several dresses but eventually decided on a tight low cut grey sparkly top that showed off my breasts and cleavage and a black skirt, black always looks good. It was shorter than I would normally wear and had a six-inch slit up the back. I bought some skimpy heeled open sandals that had much higher heels than I would typically wear. I chose some new makeup and found a stunning red lip gloss.

As we ate lunch, Karen passed me a bag which she said was a present. I glanced inside and there was some FCUK perfume (a lucky charm) and a pack of condoms.

That evening, I busied myself in the kitchen preparing the meal. Then it was time to shower and dress. I put on a robe while I carefully applied my make up. It was a long time since I had taken such care and I was pleased with the end result. The red lip gloss looked terrific.

I stepped out of my robe and stood naked in front of my full-length mirror. I was 5 feet 4 inches with 32 FF breasts. Apart from the sagging breasts, my figure still looked good and I didn't think Phil would be disappointed when he saw me naked.

My new clothes were laid out on the bed. I pulled on the bra and adjusted it. It certainly lifted my breasts, and my nipples were erect, always the case when I was aroused.  I then slipped on the suspender belt and carefully unwrapped those very expensive seamed nylon stockings. I slowly pulled them up my legs ensuring the seams were straight and clipped on the suspenders and adjusted so that they were pulling tight. I had forgotten just how good nylon stockings felt.

I had never worn thong panties before, and it struck me how brief they were, barely covering my pussy. They were very comfortable and looking at myself in the mirror I looked great and felt so sexy. I pulled on my top and skirt and then slipped into the heeled sandals. I would need to practice walking in them. Jewelry and perfume completed my outfit.

 As I stood in front of the mirror I felt and looked so good. My new top and bra certainly showed off my breasts and cleavage and my nipples were already erect and showing through the top.

I turned and bent over a little to see my skirt ride up enough to expose a little stocking top through the slit in the rear. Likewise when I sat down and crossed my legs the skirt rode up to expose a little stocking top. I could also see the tell-tale outline of the suspender clips through my skirt. I would make sure Phil knew I was wearing stockings and suspenders. I would need to take the lead tonight.

I busied myself with the meal preparation and then heard Phil’s car pull onto the drive. My heart was pounding as he knocked on the door. This was the night I was going to get laid.

I opened it with a smile and beckoned him inside. For a moment I could see him look me up and down. I noticed he had flowers and wine and eventually he gave me the flowers and said I looked sensational. I thanked him for the flowers and the compliment with a kiss on each cheek and replied that a girl should always make a special effort for a first date, I could see he liked that.

I turned and reached up to take a vase out of a cupboard to put the flowers in as Phil poured himself a beer and me a large glass of wine. I could immediately see his eyes were drawn to my legs, he had spotted the seamed stockings and I could see a bulge appear in the front of his trousers. I suddenly felt in control of things.

We enjoyed a good meal and talked freely. I explored the girlfriend situation, he didn't have one, and I said how surprised I was about that. Likewise, Phil said he was surprised that I didn't have a man in my life again to which I said I would really find it difficult to trust anyone after my experience. Throughout the meal, I noticed Phil's eyes were drawn to my low cut top and my cleavage which was hardly surprising as my nipples were so erect and visible through my top.

Eventually, with a little apprehension,  I decided it was time to move things on. I picked up my wine glass and his beer and moved to the two seater settee and put the drinks down on the low table.

I beckoned Phil over to the settee and with him sat down I had planned to change the music in the CD player to the side. Because as he sat down my skirt rode up as I bent over. I knew he would be getting an eyeful looking up my skirt at my stocking tops. Glancing back I could see he was taking full advantage of this as he adjusted the bulge in his trousers. I then sat down and slowly crossed my legs letting my skirt ride up exposing a little stocking top, I made no attempt to adjust my skirt. I was feeling so horny now.

Phil glanced down at my crossed legs and then looked me in the eye. Would he make a move? He said how much he had enjoyed the meal and my company. He said again how sensational I looked tonight and he hoped he hadn't misread the situation but he wanted to take things further and hoped I wanted the same thing. He said he wanted to spend the night with me.

I was so elated as I put down my wine, I giggled out loud and said I definitely wanted the same thing. I reached over to him and put an arm around his neck pulling him towards me, his right arm slipped around my waist. With that we were suddenly kissing very passionately, our tongues exploring each other's mouths.

I felt his left hand cup my right breast and rub my nipple but then quickly drop to my thigh and move up and under my skirt until he found stocking top and suspender. He gasped that I was wearing stockings and suspenders to which I replied they were especially for him to enjoy as he caressed my nylon clad thigh.

I dropped a hand to massage his erection through his trousers. It had been too long since I had felt an erection and it felt so good. Feeling incredibly horny I pulled away from our kiss and said that before things went any further, I must insist that he agree to two conditions; this evening must remain our secret forever as I didn't want Jon to find out his mother was fucking his best friend and that he wear a condom during sex. Phil readily agreed to both conditions.

We kissed again and I uncrossed my legs and relaxed back on the settee taking Phil with me. I opened my legs and could feel that my skirt had ridden right up exposing my panties and stocking tops. I wanted his hand in my panties.

Phil took the hint and moved his hand onto my crotch and, in a flash, he pulled aside the thin wisp of lacy nylon covering my pussy giving him full access. As his fingers touched my clitoris, I let out a gasp of pleasure and said he didn't waste any time. He gently massaged my clitoris with one finger and slipped another into my very moist pussy.

This boy knew what he was doing. We continued to kiss and I was breathing heavily as he was bringing me close to orgasm. I dropped my hand onto his hand to ensure he didn't stop and gasped out loud as I had a shattering orgasm. I lay back on the settee, my skirt was around my waist now, all modesty had gone and I realized he would be expecting something in return.

I pushed him back and unbuckled his belt and unzipped his trousers. Reaching into his boxers I could feel his erection and I eased it out and it sprang up with a fierce red shiny helmet. After so long without sex his erection seemed huge to me.

He gasped as I leaned over and licked the precum from the tip. I then took that wonderful helmet in my mouth and started to work it in and out. I was really enjoying the feel of his shaft and his erection in my mouth and it was great to hear Phil gasping with pleasure as I worked it in and out.

Not surprisingly he was very sexually aroused and soon I could feel him tensing up and he told me he was about to cum. I reached for a napkin as I took him out of my mouth, but it was almost too late as he spurted a huge ribbon of semen all over both of us. I caught the subsequent spurts in the napkin. There was so much cum.

My skirt was stained, but I couldn’t care less. I wanted Phil to fuck me. We kissed again and I said we should go upstairs and continue in comfort.

We stood up, and I led him by the hand into the hall where he reached into his jacket and took out a packet of condoms. I said he must have been planning for this to which he replied that he had hoped for it. I took his hand and led him up the stairs and into my bedroom.

I immediately started to unbutton his shirt and pulled it off. His trousers were easily undone and pulled down. His erection in his semen-stained boxers was already tenting and I carefully lifted them off and over it.

Now I could see his full length as he stood naked in front of me. He stepped out of his trousers and stood with a full erection, ready to go again. I see what Karen had meant about younger guys and, as I was about to find out, they could go all night.

Phil put his arms around me and lifted my top up and over my head and tossed it aside. He then unzipped my skirt, and I let it fall to the floor and stepped out of it.  I stood in front of him wearing my lacy black bra, black thong panties, black suspender belt, and seamed nylon stockings, balancing on my big heels.

Phil stood and looked at me for a moment and then said it was the sexiest sight he had ever seen. I said he didn't realize just how much it meant to an older woman to hear a young stud say that. And I reached up to put my arms around his neck and kissed him again.

Phil was keen to undress me; his hands reached behind me and unclipped my bra. My breasts fell into his eager hands and he fondled them and tweaked my erect nipples. Phil said that he had fantasized many times about doing this and then explored them with his mouth.

I was really enjoying this, but I was feeling really horny as I could feel his erection pressing into my buttocks. I turned around and put both hands around his neck. We kissed a long passionate kiss. I could feel Phil's hands drop to fondle my buttocks.

Eventually, I pulled away a little and said I needed him to fuck me. I stepped to the bed and lay back on it. Phil eased my panties off me as I lay back, my nylon clad legs wide apart and bent at the knee and fingering my clitoris. Phil sat on the bedside and I watched him unwrap a condom and roll it down his erection.

He crawled between my legs and positioned himself. His erection looked huge as the condom seemed to exaggerate every vein. I looked into his eyes and saw a look of pure lust as he rubbed his erection around my pussy lips. There was no going back now.

I asked him to be gentle as it had been a long time since I last had sex. And then he slipped inside me. We both let out a gasp of sheer pleasure as my wetness, and the lubricant on the condom caused him to slide in really easily.

He was on top of me and was gently pushing in and out of me each time penetrating me further. I was crying out with pleasure and encouraging him to keep fucking me and telling him how good it felt. Phil was gasping and telling me how good it felt to fuck me.

Not surprisingly we were both extremely sexually aroused, and soon I could feel his thrusts began to increase in pace and intensity and it was clear he was ready to cum. I just let myself go completely and climaxed noisily moments before he shouted and came himself. I could feel his semen spurting into the condom. He kept thrusting until it was clear we had both finished climaxing and then rolled exhausted off me and lay next to me.

We were both panting and he was the first to speak. He thanked me and said how he fantasized many times about having sex with me. He said the reality was just so much better and he would be ready to go again as soon as he had cleaned up.

While he was in the bathroom, I lay back and enjoyed the sensationally satisfied feeling one gets after a climax, a feeling I had long forgotten. When he returned I went to the bathroom and cleaned up the moisture that was running down the inside of my thighs, I was so aroused. My lip gloss was destroyed with all that kissing and sucking so I reapplied it.

Still wearing my stockings and suspenders, I returned to the bedroom and lay next to Phil. We kissed and cuddled and inevitably his hands were all over me. He was caressing my breasts and my nylon stockings.

He said the seamed nylons looked sensational and were so sexy. His fingers also dropped to caress my very wet and swollen pussy and, as I was gently holding his cock, I could feel it hardening in my hand until it was fully erect again.

I reached for a condom and unwrapped it and rolled it down his erection. I wanted him inside me again, but Phil had his own ideas. He told me his fantasy had always been taking me doggy and said the stockings and suspenders made that even sexier.

The sex was so good I happily rolled onto my front and knelt with my legs apart, my chin on the pillows and my bottom in the air giving him full and easy access to me. I felt Phil come up close behind me and his fingers were caressing my swollen and very wet pussy. Then his swollen helmet parted my pussy lips and he slid so easily into me letting out a long moan of pleasure.

Suddenly he was fucking me at a fast pace and shouting out how good it was. His hands went around my waist and he expertly massaged my clitoris as he continued to fuck me. This time was lasting longer than the first time and his stamina was amazing as he kept up a relentless pace.

I could feel my next climax welling and he suddenly shouted out he was cumming as he pumped his load into me. This just tipped me over the edge as I climaxed. It was sensational sex.

That night will remain in my memory forever. We had sex several more times until neither of us had any energy and we fell asleep in each other's arms. Our relationship has continued and the sex remains fabulous.

 

 

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