Almost Jason Almost

It's early on a Saturday morning and I'm just lying here in bed stroking my cock, something I do quite often.

My fantasy person while stroking is the lady of the house, no not my Mom, but my best friends Mom.

My parents travel a lot for business and when they're away I stay at my friend's house. I even took over their guest room as my own. Even though I'm 18 now I still stay here when possible, I like the company and they always make me feel welcome. I'll be going away to college the end of the summer, so I might as well enjoy this while I can.

My name is Jason.

The family I stay with is my best friend James, he's two years younger than me, a great guy, his sister Cheryl, a bitch in training, who is in her early teens, the father Jim, and the object of my masturbation fantasies Gloria.

Gloria and her husband are both very successful, Gloria came from money, but they both have very successful careers now. They are liked by just about everyone; Jim was my little league coach and Gloria is active in several community groups. They also host a lot of cook-out pool parties in the summer.

Now the important stuff, Gloria is 43 years old, she runs to keep her figure and believe me its working. She's tall and it's all legs! From snooping in her hamper I know she wears a 36C bra, has nice panty's, but don't know sizes, they do smell nice.

All of James and Cheryl's friends like Gloria; the guys because they're hot for her, but mostly because they treat us like adults, even if we don't always deserve it. James and Cheryl's friends are always welcome to come over and use the pool and look at sporting events in their huge den.

The hottest part about Gloria is that she never acts like she's as sexy she is. I heard my dad say once that she has no idea the effect she has on men. I don't think he was saying that to my mother, but I did over hear him say it to someone.

All the guys call her a MILF and one knucklehead a few years ago told her that, thinking she wouldn't know what it meant. She just stared at him when he said it and he ended up saying he was sorry. I did catch a smile on her face though.

I've seen her in different degrees of undress on many occasions which only adds to my masturbation fodder.

The first time was several years ago during the summer. They didn't have the pool house built yet, so you had to go into the kitchen for a cold drink. I was playing in the pool with James and a few other guys and was elected to get us some Pepsi's.

I walked in the backdoor and was heading for the refrigerator when I collided with Gloria, we almost both fell over. She was completely naked, I just froze and stared, she mumbled something about going to the changing room to get into her swimsuit and beat tracks down the hall. I looked at her beautiful butt bouncing as she walked away. Later in the day she pulled me aside and said she was sorry for being so careless about running around the house naked. I couldn't think of anything cool to say, so I just said that's okay.

On another occasion she picked me up from my parent's house to bring me to her home because my parents were going on a trip. I was riding shotgun and looked over towards her and her skirt was all the way up to her waist. I couldn't see her panties but I saw some beautiful bare legs. She just drove and talked like everything was normal. I had an erection, which I must confess is pretty much normal when I'm around Gloria.

One other time I was in the house and was walking down the hall and noticed the bathroom door was ajar. I looked in and Gloria was butt naked on all fours cleaning the tub. I've heard her joking about doing the house cleaning nude, but thought she was kidding because I know they have a cleaning lady come in twice a week. That was the first time I ever saw a pussy from the rear. I was more surprised that it was back there than the fact I was looking at Gloria. I peeked at her for the longest time, but when I thought I heard someone downstairs I left. There wasn't anyone down stairs when I got down there, which really pissed me off.

The thing that has me wondering about these encounters is they only happen when I'm alone. I mean, nothing sexy happens when her family is around. I'm not sure if it's my fantasy's taking control over my mind or could it be that she's planning these things to happen. I can't imagine she would, but it's so hot thinking that she might be.

The door to the guest room opened and I'm lying here on top of the covers with a raging hard on. I can't think of anything to do, so I pretend I'm sleeping. I have my eyes are just barely open and I see Gloria walking to the closet on the other side of the room. I move my arm over my face so it would be more difficult to see if my eyes were open. She's getting a blanket from the closet and she's turning around to leave. She glances towards me and stops in her tracks. She's looking at me naked! She moves a little closer and I'm thinking she might be able to hear my heart beat. She's at the edge of the bed looking down at me; this is the sexiest thing that has ever happened to me. If there's a God in heaven she'll touch me, but she doesn't. I thought her hand was moving towards my cock, but she pulled it back and left the room.

I'm playing this event over in my mind when the door opens again.

I see her walking towards the closet again, get something and head for the door. It's not Gloria, it's her friend Tracy, another hot women. She walks slowly towards me and is standing right next to me. She looks for a minute then reaches out and takes my cock in her hand, gives it a squeeze then gives it a few strokes. I can't believe it, her head is moving towards my cock and she places the head of it in her mouth. Damn if I almost didn't moan. She sucked it and licked it, then got up and left the room.

I'm trying to figure out why Tracy was here because Gloria knew I was in here naked. Naw, she couldn't have sent Tracy in here to look at me also!

It wasn't 10 minutes later when the door opened again. Who could it be this time?

It was both of them!

Tracy held my cock in her hand and I could hear her whisper for Gloria to touch it. She didn't answer, but she took it in her hand and gave it a squeeze. I think I died and went to heaven.

I'm not sure exactly what happened next, but one of them started to giggle then the other followed suit. Before I knew what happened they both left the room.

I waited for them to come back, but they didn't.

I started to jerk in earnest and when I did, come it shot up my chest. I wish it was in Gloria.