A Milf Story as Told by the Mother

My name is Meg Williams and I am a MILF. At 43 I could easily pass for 30 or even younger. I am 5' 8" and I have the time and resources to take good care of myself along with good genes. I have long legs and a tight ass from working out and playing sports like golf and tennis. I have long brunette hair and an all over tan. My tits are my best asset. They are 36 DD and are heavy but don't sag. They are all me, with big areolas and nipples that stay hard. I have worked out more lately to stay in shape. My abs are tight and well defined. I do this to keep up with my son who I have been fucking for the last 1 ½ years.

His name is Billy and he is 22 and a recent college graduate. He is very handsome and mature looking. Many people think he is older then he is. He is 6' tall and 185lbs. He played sports in high school and college. He took a job with a local company even though he had out of state offers. I guess being close to me was more important the money, even though our family has plenty of it. Oh yes, I forgot to mention he has a very large cock too.

Billy's father, my husband, has a high paying job that requires a lot of travel. He spends time playing golf and entertaining clients. I know he cheats on me, but I don't really care. Our marriage at this point is for convenience. I spend a lot of time at Billy's apartment. Everyone in the complex thinks I'm his girlfriend and we have done nothing to confirm otherwise. We like acting like a couple when we go out.

Of course the sex is great. The only issue we have is Billy's father had a vasectomy and I can't take the pill. I tried using a diaphragm but it's too much hassle. We both hate rubbers so lately I have been keeping close tabs on my ovulation cycle. I have my period like clockwork and I can time the exact couple of days I am in danger of getting pregnant. Other then having to explain a pregnancy to his father having Billy's baby would be wonderful.

Billy has been very successful at his new company. Even though he has been there less then a year he has had two promotions. We are celebrating his most recent one with a family dinner at the house.

"I have some great news." Billy said after dinner.

"What's that son?" his father asked.

"The owner of our company, at the end of the fiscal year, takes all the top performers on a trip to some tropical location. My department was number one so I get to go to Jamaica next month." he announced.

I said, "That's great Billy. Jamaica should be nice and warm this time of year."

He said, "Yes, we are staying at a first class resort. There is one thing though. There are about 100 people from the company going and each of us can take a guest. It's kind of mandatory. I don't really have anyone I would want to take so I was thinking. Mom why don't you come with me?"

I was a little shocked that he asked this in front of his Dad. I smiled seeing through his plan and played along. "Oh you don't want to hang out in Jamaica with your old Mom, do you?"

He said, "No it would be great we could play golf and we haven't been on a family vacation since I went off to college. Please Mom, say you will go. Dad, you think she should go right?"

His father paused for a moment then said, "Sure, I think you two would have a great time."

So I agreed, like I would say no, and all the arraignments were made for our trip. Of course I had to have a new wardrobe so I spent more of the hubby's money on it. Some new resort outfits and a couple of new swimsuits, special ones. When I looked at the calendar and the dates of our trip, which was 4 days and 3 nights, I realized something. The dates would fall during the time of the month that I should be ovulating. He would just have to use a rubber, yuck, or pull out or something.

He told everyone at work he was taking his girlfriend and showed them some pictures of us. So when departure day arrived when we got to the airport many of his coworkers came up to me to introduce themselves. I was wearing a white cotton golf shirt and some khaki shorts that showed off my tan legs. The bra I was wearing was very thin so my nipples showed through easily. The plane we were on was a charter flight with the only people aboard from Billy's company. I took a window seat and Billy the aisle seat next to me and we took off.

It was about a three hour flight and one hour into it Billy leaned over and whispered into my ear.

"Hey are you a member of the mile high club?" he said.

"Ha ha, no are you?" I responded.

"No, so we can initiate each other, come on." he suggested.

"Billy we'll get caught, you work with these people." I protested.

"No we won't," he said. "It will be easy, I will go to the last lavatory at the back. You wait a couple of minutes and then you go back there too. Knock 3 times lightly on the door and I will let you in."

Before I could say anything he got up and headed to the back of the plane. My heart was pounding. I really didn't care about any of these people but I didn't want to get Billy in trouble. The thought of doing it with that risk was making me wet though. Two minutes went by and I took a deep breath and got up to get to the back of the plane. As I walked down the aisle all the men would look at me and smile then their eyes would travel down then back up stopping on my chest.

When I got to the back of the plane it was quiet and nobody was waiting in line for the bathrooms. I stood in front of the last door and lightly knocked 3 times. I heard the latch open and I opened the door and stepped in closing and locking it behind me. Billy was sitting on the commode seat with his pants down and his big cock was rock hard and sticking up. I put my finger to my lips and said "Shhh." I turned around and pulled my shorts and panties down exposing my ass and pussy to him. It was really cramped quarters in there for two people. He guided me back and I sat down on his cock. The head protested for a moment then slipped in my wet cunt. I slide all the way down on him and we both groaned from the tightness. We usually don't do the quickie thing but this circumstance called for that.

I started to ride him up and down, taking full strokes. He helped by lifting my ass up then pulling me back down. Our speed picked up quickly and from all the excitement of doing it on an airplane and the risk of getting caught I knew we would both climax soon. He really couldn't pull out or we would have a big mess to clean up so I decided to risk it and let him come in me. Tomorrow was really the day I had to worry about. I felt him swell up and groan again and then I felt his spurts inside me. I had a nice mild orgasm too. When we were done I got up off of him and told him to clean us up while I was bent over with my ass pointed at him. He wiped us down well with tissue and I put some in my panties to catch any more of his cum that might leak out of me. I pulled my shorts up and got ready to exit.

I checked myself in the mirror and then slowly opened the door and stepped back out. I made my way back down the aisle to my seat and I knew guys were watching my ass. A few minutes later Billy reappeared and sat back down next to me with a big goofy grin on his face. When a stewardess brought us some drinks later she bent over and whispered to the two of us, "Welcome to the Club."

Billy and I just smiled back and I wondered how many others knew.

The rest of the flight was quiet. We landed and went through customs and boarded a shuttle bus to the resort. It was a beautiful hotel on the beach, very exclusive and private. We checked in and went up to our room. It was a large suite with a balcony that looked out over the lawn and pool. Beyond that you could see the ocean. It was mid afternoon and we had some time before we needed to get ready for the dinner that night so we laid down on the bed for a nap.

The alarm went off a couple of hours later and it was time to get ready. I went in the bathroom and turned the shower on. I got undressed and got in the shower first. I was letting the warm water run over me when the door opened and Billy joined me. It was a large shower with plenty of room for two. The water felt nice as did his strong hands caressing my body. I put my hands on the wall of the shower and bent forward. Billy stepped up behind me and rubbed his hard cock on my wet pussy. He pressed it to my entrance and pushed the head in. Slowly he worked it in and out. He reached around and started rubbing my swollen clit as he pumped me. Very quickly that got to me and I orgasmed as he pounded me. He pulled out but he hadn't come yet. I knelt down as the water ran over us and took his cock into my mouth. I sucked and slurped his cock as I stroked him. With the other hand I played with his big balls. They were the size of large eggs and his scrotum was loose and hung down low.

"Oh God I'm cuming." he said.

I kept stroking him leaving just the head of his cock in my mouth. I felt it swell up some then the first volley shot down my throat. A couple more shots and I sucked him dry. He was weak in the knees but we managed to wash each other and got out of the shower to get ready for dinner. I decided to wear a floral sundress. It was strapless and showed off my tanned shoulders well. It also showed off my cleavage and I had doubts that I would be able to keep my tits from spilling out.

Billy wore lightweight grey slacks and a black polo shirt. He looked at me and said, "You look fantastic. They won't be able to keep their eyes off of you especially if you bend forward too much."

We left our room and walked down to the lawn near the pool. They had set up tables there for the big dinner. We had assigned seating and we found our table. Billy introduced me to everyone. We sat down and everyone commented on what a nice couple we made. I smiled to myself knowing the truth of course that I was his mother. I kept noticing that some of the men from other tables would get up and circle our table on their way to the bar. Then make a point of walking back past us on their way back to their tables. I smiled knowing they were trying their hardest to look down my dress hoping something would spill out more.

One of the women that work with Billy came by and whispered to me, "Billy is quite a catch, but it looks like you might have succeeded in taking him off the market. You two are so cute together. I bet you would make beautiful babies."

I think she was a little drunk, but I actually wondered if we would. After dinner there were a few speeches then a reggae band started playing. We tried to dance to a couple of songs but decided to head to the beach instead. We took off our shoes and went down to the water. We held hands as we walked on the wet sand. There we some other people there so we couldn't get too carried away. Tomorrow morning was our golf outing so we made our way back up to our room.

We got undressed for bed. It had been a long day and we were both tired. We held each other close, our naked bodies entwined. I thought Billy might just drift off to sleep but he started caressing my breasts. He bent to gently suckle my nipples. It felt wonderful and made me wet. He let go of them and slide over on top of me. He was hard and slowly and gently entered me. We kissed deeply and as out tongues played together he pushed his entire length in me. We had become very attuned to each others bodies and picked up a natural rhythm. It was so loving and passionate I forgot all about consequences and any thought of risk. I held him close and wrapped my legs around him. It was his third orgasm of the day and I cried out with mine as he emptied himself in me. We drifted off to sleep with gentle kisses and whispered "I love you's".

We woke up early and got ready for our golf outing. After breakfast a shuttle took us to the course. We had brought our clubs with us and they were already set up in the cart we were assigned. It was a scramble tournament and we were paired with a couple of guys from Billy's department. There were actually only a couple of other women playing today. We arrived at the tee we were to start from and I noticed the foursome behind us was the company owner and some of the higher up exec's. We let the other two guys in our group hit first. Billy had played on the high school golf team and had gone to college on a golf scholarship. I had played in high school and college and at one time thought about turning pro. Of course the men behind us had no idea of this.

I was wearing some cute white golf shorts and a peach colored tank top. After Billy smoked his drive down the middle at about 300 yds. I stepped up to hit.

The guys behind us had already started drinking and one said, "Hey Hon, you can hit from the ladies tee we don't mind."

They were all laughing and back slapping.

I smiled back at them and said, "You know boys, you might have picked the wrong foursome today. I'll hit from here to keep it fair."

I took out my custom made Calloway driver and hit a screaming fade drive that when it finally quit rolling was at about 325 yds. I stood there admiring it then turned around to see their reaction. Their mouths hung open in disbelief.

I smiled and said, "Good luck gentlemen."

As the round progressed we played mostly Billy's or my shots. At the turn we were 8 under. I wasn't really trying to show off but it was easy when you saw the same putt 3 times before you hit. If Billy didn't make the putt I usually did. We finished by shooting a 59 which was 13 under par. We won the tournament by three strokes. I am sure some of the other all men's teams were a little embarrassed to being beat by a team with a woman on it. The owner of the company gave us our trophies and when he handed me mine instead of shaking his hand I gave him a hug letting him feel how big my tits really were and kissed him on the cheek.

We got back to the hotel about 2 PM and we decided to go to the pool. I put my hair up and picked out one of my new bikinis. This was a white one and it was made of a special material. It was supposed to let the sun's rays through so you would not get tan lines. It wasn't too risque of a cut, but it did show a nice amount of my ass and the top gave some support but I spilled out of it some. I put a nice gauze-like wrap around my waist and got my sunglasses and we headed for the pool.

It was crowded and I could feel a lot of eyes following me. We found two pool lounges together and set our stuff down. We ordered drinks and I undid my wrap and started oiling up to work on my tan. Billy was wearing his normal board shorts and ordered us some drinks. After a couple of daiquiris I was feeling good and we had been in the sun about an hour. I decided to take a dip in the pool to cool off. I got up off the lounge and slowly made my way to the steps and into the pool. I waded out a ways then lowered myself into the water. Now there was only one problem with a swimsuit like I had on. The material let you tan but in order to do that it had no lining. When it got wet it was virtually see through. Of course I knew this, that's why I bought it.

When I came up out of the water my top was plastered to my skin and was so transparent that you could plainly see the outline of my areolas and nipples, which were hard. I walked through the water over to a ladder near where we were laying out. I climbed the ladder and the fabric of my bottoms clung to me and the outline of my pussy lips was noticeable. I saw Billy smiling as I walked back to him. He knew what I was doing. I saw a couple of women punch their husbands because they were staring. It was like a wet t-shirt contest and I was the winner.

After a couple of more hours in the sun we got up and headed to our room to get ready for dinner. We didn't want to be late so there was no hanky panky. After out shower I put on a sequined evening dress. It was a tight fitting halter style mini dress. Billy put on a lightweight poplin suit. This was to be a more formal dinner with awards. We entered the big dining room and found our table near the front. We had a steak and lobster dinner and then the awards were handed out. Spouses or girlfriends went up on stage with the winners. Billy's name was called and I got up to go with him. The owner handed him his award and we stood on either side of him to take pictures. He had his arm around each of us. Of course his hand was under my arm right where my boob was pushing out of the side from my dress. As the picture was taken he gave me a little squeeze. I just smiled and as we left the stage I noticed a lot of flashbulbs going off.

After the awards there was dancing to a DJ. I was really enjoying myself. Many of Billy's bosses asked me to dance with them. Most of it was innocent except for a few gropes followed by the "Oh I'm sorry" routine. One guy, who after I started dancing with I found to be really drunk, asked if we could go to my room and fuck. He just had to see my tits.

I whispered in his ear, "Sure Baby let's go, but first let's go ask your wife to join us. We can do a threesome."

I knew where his wife was sitting and when I started to lead him back to his table he sobered up quickly and said Goodnight. I laughed as I headed back to Billy. It was late and we were both tired so we headed back up to our room. We got undressed and climbed into bed. I think the sight of me dancing with other men got him worked up. He wanted to claim me as his again. I let him take the lead. He had me on my hands and knees and entered me from behind. I submitted to his will and moaned and asked for more of his big cock. We were both a little tipsy and he was lasting a long time.

He flipped me on my back and reinserted himself. I wrapped my long legs around him pulling him deeper. Through all the passion I knew I had to say something.

"Billy, listen to me. You need to know something. If you come in me I might get pregnant. I may or may not already be pregnant if I have figured the timing right I have made a decision. I love you Billy and I want your baby, but only if you are willing to deal with that."

As he continued to pump he said, "Mom I love you too. I want you to have my baby more then anything. We'll find a way to make it work."

I pulled him down to me and kissed him deeply then whispered to him, "Then do it Baby, I love you. Fill me up, I want to feel your big cock spewing inside me."

With that green light he grabbed my hips and started pumping with a purpose. He was hitting bottom with each thrust, mashing my cervix. He was almost there when I exploded with my own orgasm. I thrashed about crying out loud enough that I am sure the people next to us heard me. As my pussy clamped down on him he unloaded a huge gush of sperm in me. Each thrust pushing it farther up inside. He finally slowed down and collapsed on top of me. I held him close and we fell asleep with him still firmly plugged in me.

The next morning we woke up to a beautiful day, beach day. Billy ordered some room service breakfast and we prepared for the beach. I picked out a bikini I had bought specially for this trip. It was very expensive. Why, I have no idea, there was very little material used to make it. The top was basically two little pieces of black triangular material attached with some string. When I put it on they barely covered my areolas. The bottom was black as well and looked like a g-string strippers wear, leaving my ass basically exposed.

When I put it on Billy laughed and said, "Why wear anything?"

I had a gauzy short kimono like robe I put on for the walk to the beach. I left it untied so the front remained open. It was about noon when we headed for the beach. We had to walk by the pool on the way and there were a lot of people there already. I had my big sunglasses on and a floppy hat and smiled to myself as men would stop cold and stare. When we got to the entrance to the path that led to the beach there was a sign explaining the rules. Pretty normal stuff except for one line. It said "Adults only." Billy and I weren't quite sure what that meant and we kept going. We reached the beach and found a couple of lounges with an umbrella and small table. We put our stuff down and settled in. Soon a waiter came by to take drink orders. We both ordered some Red Stripe Beer.