A dream come true….almost! Pt 1

[Wifelover]

Growing up, my best friend’s mother, Lesa, was one of the sexiest women I knew. She is a tall brunette with long legs, great butt, and large tits. But, she’s also the nicest lady ever! Always has a smile on her face, loves to talk to people, and is just a genuine person! She’s also a pretty big flirt, or at least I think she is. Her husband passed away when Bob, her son and my friend, was young. Fortunately, he left her taken care of and she hasn’t had to struggle like so many single mothers. I used to fantasize about sex with her on a regular basis, as did most the boys in the neighborhood I guess. We all used to hang out at their house and she would feed us, take us places, and just sit and talk to us if we wanted. We all knew we could call on her anytime if we were in trouble. Because of that, I almost feel guilty that my main desire was to bone her!

I’m 22 now and Bob has gone out of state for a job he recently took and I have had to find new friends to hang out with. Recently, a few of us went to a C&W bar and who did I see but Lesa! She looked hot in a short denim skirt, tank top, and boots and had guys waiting to dance with her. When I saw her, she ran over and gave me a huge hug, it had been about 2 years since I’d seen her. She’s now 40 years old but damn sure doesn’t look it! She actually asked me to dance with her, which I gladly accepted. As we moved around the floor I had to fight to avoid staring at her tits as they bounced up and down. Her nipples sticking out against the shirt, she wasn’t wearing a bra! After a couple of songs she went back to her table and sat with 2 women and 3 men, the men glared at me before looking away.

I am nothing for them to be jealous of. 5’8” tall, 155”, skinny, not really a ladies man at all. At this time I’d had 2 girlfriends and had embarrassing sex with 1 of them. I have had friends try to set me up, but I’m always instantly in the friend zone after 1 date. It’s not that I”m ugly, I’m just rather plain looking and tend to speak my mind, some people don’t like that. Anyway, I was talking to the 2 guys I came in with, each of them wanting to know who the MILF was that I danced with! I told them who she was and they were goading me to dance with her again. One of them, Jason, eventually telling me that you could see her butt cheeks when she would spin around, I guess she was wearing a thong! No Bra and a thong! I could hardly believe this was Lesa, Bob’s mother! We did dance again and I asked her about her friends. She said she worked with the guys and the ladies she’d known since college. She then asked how I had been and if I was dating. I told her no, girls just don’t seem to be interested. She shook her head and said “As cute as you are? I find that hard to believe.” But I somehow felt it was just her being like a “mom”. We danced 3 or 4 more times that night and I was curious if this was a regular thing for her. She told me she comes here a couple of times a month on Fridays, but that’s about it. I asked if she was dating anyone, she told me no…she is just friends with a few people. She did say that one of her friends has a boat and that she’d invite me the next time they took it out. She came over and told me goodnight around 11:30 and kissed me on the cheek. I hated seeing her leave because I’d had more fun with her than any dates I’d been on in years, or ever! Holding her body against me when we slow danced was incredible! I couldn’t help get an erection and was afraid she’d notice and get mad but, if she noticed, she didn’t let on.

I figured I wouldn’t see her again for a long time but, about a month later, she called my cell phone and asked if I wanted to go out with her and a few friends on the boat. I said yes and she told me to invite a few friends if I wanted. I said I would, but knew I wouldn’t. I got directions to where the boat was docked and agreed to meet her a week from that coming Saturday. When I arrived and saw the boat, it wasn’t what I expected. I figured it was a smaller boat large enough for 4 or 5 people, but it was probably large enough for 10 or 12! Lesa was just getting onboard when I walked up. She looked quite hot in the short cover up she wore over her swim suit and the floppy hat and sunglasses. She introduced me to Phil, the owner of the boat, who was about 65 years old and apparently wealthy. I asked who else was coming and Phil told me if none of my friends were coming then it was just us and his assistant Angel. I said it was just me and got onboard with my bag. Within 20 minutes, Angel was steering the boat away from the dock. Once we got out a little bit the water was pretty smooth. The 3 of us went the front of the boat and sat on the benches there, Phil offered everyone a drink. I took a beer and Lesa sipped on some scotch on the rocks while we talked. She soon decided to get some sun and removed her cover up and lay down on the padded bench. I had a hard time looking at her because i didn’t want anyone to see me with a hard-on! Her swim suit was sex as hell and her body was unbelievable! I never wanted a girl/woman so badly in all my life! The suit was black and cut high up on her hips. The front was cut down almost to her belly button and tied around her neck. From behind, it could not contain her full ass, her butt cheeks proudly on display. When she moved to one side or the other, the fabric would pucker and threaten to expose her entire chest.

This was the start of something fun. More to come…

 

[Wifelover]

After cruising around for a while, Angel headed back towards the dock but then entered a cove and anchored. There were 1 or 2 other boats there but not many. A few people were in the water swimming so I decided to get in as well. Lesa, Phil and Angel were still on the boat talking. I got back onboard a bit later and Lesa was trying to take a nap saying she’d just taken a Xanax and seemed to be feeling no pain. She only lay there for a minute before getting up again. Another boat pulled up and anchored a few feet away, loud music was playing from their large speakers so Phil turned his music off. Lesa seemed full of energy now and was up and dancing. The party boat near us had 7 people on board, 3 guys, 4 women, all appeared to be in their 40s - 50s and drinking and dancing themselves. After speaking to Phil, they eased their boat closer and tied off with our boat so that people could move from one to the other.

Soon, 2 more boats pulled up and tied onto their boat making 4 of us altogether. The smallest boat was occupied by a young couple, probably mid to late 20s, and the other was much smaller than Phil’s boat, but easily double the size of the small one. That boat had 3 guys and 3 chicks on it who looked to be around Lesa’s age, but she looks young so I guessed them as mid 30s. We had quite the range there partying now. Other boats pulled in and anchored in the cove and soon it was quite the party. People were going from boat to boat mingling and drinking, except Angel who sat in the cabin reading a book and occasionally watching. Lesa and 3 of the other ladies were all dancing on the front of Phil’s boat drawing lots of attention from every guy nearby. The young lady from the small boat was particularly energetic and soon took her top off. The guys hooped and hollered and started encouraging the other ladies to do the same. One by one they did, all except Lesa who was wearing a one piece suit of sorts. It tied around her neck, just a string, and at her hips but it was the string around her neck that held it up. Everyone was cheering and practically pleading with Lesa to take her top off but she just smiled and shook her head. One of the girls was dancing with her and starting grinding her from behind. 2 more ladies joined them and quickly removed their tops and then began doing shots off each other’s tits!

The guys continued to try and convince Lesa to drop her top, she continued to refuse. She DID however do a couple of body shots from the other girls which was quite sexy! Lesa made her way over to a couple of the other boats and had a couple of drinks before getting back aboard ours. There were 6 or 8 ladies on Phil’s boat dancing, 5 were topless, leaving Lesa and 2 others with their tops on. The youngest of the group was once again dancing behind Lesa and reached around and grabbed her tits cause a loud cheer from the guys. I was standing up front so I could see and when she pulled the suit to the side and flashed Lesa’s tits I had an up close view. Lesa quickly covered up again but didn’t seem bothered and she and the young blonde continued dancing. The blonde started acting as if she was going to untie Lesa’s top. She was behind her so Lesa didn’t see her, but the guys did and were screaming “Do it!” She teased a bit then gently started pulling the string, though I don’t think Lesa noticed. She had it almost untied then stopped and shook her head laughing. Everyone kept yelling but she just laughed shaking her head then, she reached up and pulled it the rest of the way. What happened next shocked all of us I think. The top fell down, but so did the rest of the suit…the weight of the top pulling the rest of the suit down to where it almost fell completely off! I don’t think she knew at first because she was still dancing but it only took a few moments to realize she was almost naked in front of everyone!

The rest of the story coming shortly…I realize it’s long and dull so far. Don’t continue reading if you need a simple story about fucking.

 

[Wifelover]

Lesa squealed when she realized she was naked and quickly squatted down and pulled up her suit and tied it back around her neck but it was tied very loosely. When she moved her tits were exposed and the front of the suit sagged down frequently showing her pussy, which was trimmed in a very short landing strip above her vagina. I was standing right beside her and heard her tell the girl who untied her suit “I can’t get naked here, David is like my son!” The girl asked who David is and Lesa turned toward me and pulled me over and said “This is David! Isn’t he just the cutest thing?” Then she whispered, “He’s was best friends with my son since kindergarten…I think he’s still a virgin.” She had pulled me in front of her so we were facing one another and started dancing with me. As she did, there was nothing left to my imagination! I could see her tits and pussy lips, I had already seen her ass, and she was pressing against me as we danced. Phil came over and held out a bottle of coffee flavored Patron after taking a drink himself, he handed it to me and I took a big drink. Lesa was smiling as she looked at Phil and said “You trouble maker you! You KNOW I shouldn’t be drinking that!” But she immediately grabbed the bottle and took a long drink. For the next 45 minutes the 3 of us passed the bottle to one another, though after a couple of drinks I just pretended to be drinking.

Soon, people started getting back on their boat readying to leave. Phil and Lesa were drunk and Lesa asked him to help her lay down. He laughed and said someone needed to help him but, between the 2 of us we made our way to the cabin to put her in the bed. When we got to the bedroom she managed to stand without our help and said “I can do this on my own, I don’t need help.” And she then untied her suit and let it fall to the floor. Phil asked if she wanted to cover up, but she said “No need…David has been peeking at me since he was a teenager…isn’t that right sweetie?” I’m sure I blushed but couldn’t form any words so she put her hands around my neck and said “It’s ok, I knew it even then. You were a teenager, you couldn’t help it.” Then, she leaned in and kissed me so I kissed her back with my hands on her sides afraid to touch her naked body. She pulled me close with her arms around my waist and her body pressed against mine. Phil had moved up behind her and was kissing her neck when we all 3 lost our balance and fell onto the bed. Lesa and Phil started laughing and that’s when I noticed he was naked and had a huge hard dick! I was still wearing my suit so I slid it off quickly and tossed it on the floor, though my erection was tiny by comparison. She and I continued kissing as Phil fondled and played with her breasts. I then began kissing her neck and eventually her nipple as well!

Lesa was moaning and telling Phil that she was going to need his big cock soon. I didn’t want to try and fuck her after that, so I tried to roll on top of her but she stopped me and said “We can have some fun, but you aren’t going to fuck me…understand?” I asked why and she said “Because it would just be too weird! I used to babysit you years ago, you were best friends with Bob, it wouldn’t be right.” I was actually fingering her pussy as she said this and I kissed her again and eventually found her clit because she let out a moan and said “There you go! That’s what you want to work on.” I continued playing with it, she would frequently moan but a couple of times she said “Easy…not so rough. Gentle little circles…yes, just like that.” I’m sure she finally came and then she smiled at me and told me to lay on my back and she began jerking me off. It took about a minute and I shot my load, embarrassed…I apologized but she told me “That’s ok, it’s normal for a young guy like you. You’ll be able to last longer soon.” She then rolled onto her back and Phil climbed on top of her and she let out a loud gasp when he entered her pussy. He was quickly moving in and out and she was moaning louder. I started to get up but Phil said “Don’t leave, she wants you to watch.” So, I lay back down and watched as he made her cum several times, the last time she shook all over. I was hard again from just watching and tried to get her to let me fuck her but she again told me no.

We all fell asleep on the bed, naked, as Angel took us back to the dock. He left without a word leaving us there asleep. I woke a few hours later and realized it was late at night. Lesa and Phil were nowhere to be seen so I got dressed and went upstairs where I found them sitting and talking. I wasn’t sure how to act, afraid it would be very awkward, but the smiled and Lesa asked me to join them. I sat down and we talked for a bit then Lesa said she was going back to bed and headed to the cabin. Phil looked at me, I could tell he wanted to say something but he was hesitant. Finally he said “I know you’re disappointed. Lesa has told me about you. About how she saw you peeking into her bedroom when she dressed, how you used to follow her around like a puppy dog. I told her she should fuck you just to make your fantasy come true but she still thinks it would be too weird. I talked to her for a long time before convincing her to do what we did, she refused for a long time. But, I’ll make you a bet. The next time we take the boat out, if you come with us, she’ll fuck you if you want. But, once she does, she may not invite you anymore, so you’ll have to decide if it’s worth it or not.”

Since then, I have made excuses the few times they’ve invited me. I’ve been to their parties and danced with her where she has no problem with me fondling her ass as we do, or even squeezing a breast now and then. I’m dying to have sex with her but, so far, I haven’t.