First Experience, have to boast

[JM1412]

Hi all! New poster here... I had my first Milf experience last weekend and im still excited about it so i needed some forum or theater to talk about it. The way it happened is a little shady, but i will never forget it. Enough for the preamble, let me begin:
Last weekend my girlfriend (Jackie) and I went to her cousin's (Lisa) house to visit her and her family. Ive had a crush on Lisa since i started dating Jackie, but obviously, could never say anything. In the last few months, the crush has gotten worse as ive been able to spend personal time with lisa since her house is in the center of my sales territory. Nothing has ever happened, but i think we both had certain "vibes." Last weekend, they came to fruition and in a big way. Last saturday night Jackie, Terry (lisa's husband), and i went out to dinner and got hammered. We got home and pretty much went right to bed. The next morning though, things got real. I woke up with a splitting headache and raging morning wood. I desperately needed to take some advil and take a piss. I assumed that it would be safe to just get up out of bed, run down the hall and go to the bathroom with this thing pertruding out of my shorts. I was wrong. I didnt want to wake Jackie so i crept to the door and out of it. When i was shutting the door from the hall side, i happened to look up and there Lisa was, still in pajamas holding the laundry, and by now, checking out my boner. She just smiled at me and moved to the side as i sheepishly let myself in the bathroom. I was mortified but what happened next shocked me. I was finishing up my pee when i looked up and into the mirror in front of me. Lisa was standing there, waiting for me to turn around. As i did, she put her hand up to me when i went to flush so as to tell me not to. I didnt, and that was the start. She came up to me, right against me and said, "when you're close, reach back and flush." I had two thoughts in my head. 1. that was just crazy enough to work, and 2. this chick is so sexy. After she said that, she got down onher knees in front of my still very erect penis. she slowly started to kiss and lick the tip of my penis and w/o warning, jammed my whole cock into her mouth and started sucking. The whole time she just looked up into my eyes, staring and sucking. I was so turned on and very close. I think she knew that and quickly pulled away to whisper "flush if you're going to.." not 10 seconds later, i flushed and came straight in her mouth. She swallowed every bit of cum, and got back to her feet. With that, she winked at me and whispered, "go back to bed." I snuck back to the room and jackie was asleep so i knew i was ok. I laid there thinking about how cool it was and what, if anything, would happen next. I got my answer a couple hours later.
We were all sitting there, Terry, Lisa, Jackie, their kids, and I when Lisa said, "i should go to the store to get some stuff for dinner." Jackie volunteered to go help her but the kids started whining and wouldnt let her go so i volunteered. Lisa said, "that sounds great, lets go." Terry, very unsuspecting said, "thank god, i hate the store." I grabbed my keys so i could drive. We were in my car and Lisa said, "let me explain earlier." I told her there was no need to, that i had been feeling everything she had been but i had one regret. She asked what it was and i said, "I wanted to have sex with you. the BJ felt great, but i had a lot more in mind." She said, "if you have a 'sales trip' tomorrow, ill give you the craziest experience in the world after the kids go to school." I snapped my head over at her and said, "you got it!" We didnt talk about it or acknowledge anything for the rest of the time i was there. Eventually Jackie and i left and went back to our place. I couldnt focus on hooking up with Jackie though b/c all i could think about was her cousin. Sure enough, the next morning came and i showed up at Lisa's. She didnt disappoint. She answered the door in sweats, hair pulled back and a tee shirt and said, "i couldnt get dressed all up for you b/c i want the very opposite. get in here and f--- me!" i slammed the door behind me and ran up the stairs behind her. The rest is hazy because of how sexual it was but i know how good it felt. i wound up being there about 3.5 hours. When i was getting cleaned up and ready to leave, she smiled at me, kissed me, and said, "until next time?" i said, "i have a sales trip in a month, we'll get together." "great" with that, i left. i met Jackie back at our place when she got out of work. We had the greatest sex we've ever had.

Sorry for rambling like that, i just cant get over what happened. Hope you enjoyed my story!

[El Suave]

HOt stuff man.. sounds like you really got lucky there! How old was she btw?

oh.. and welcome to TSS! ;)

[JM1412]

She just turned 40 two months ago.

[niceandspicy]

Older women are hot. Well done lad! :)

[Fila]

:) wow..what a way to be inspired! lol

[StillWantMore]

Ooo, you are so lucky, you and her both! Wow, I'd love to be in your shoes Man! Thanks for posting your story, it's good "boner fuel."

:appl:

[ajvar]

Keep it Up

[JM1412]

The first experience i had with Lisa was amazing, i never imagined that i would experience anything remotely close to that again and then i met my real estate agent. After that experience, i said, "no way, not a chance." well, thank god i was wrong. This past saturday night, i had the ultimate MILF experience. Every guy has that one MILF that they fantasize about, the one that they know is never going to happen and wouldnt know how to act if it did. That was my event this past saturday and since im still in a haze from it, i have to share the story somewhere.

My MILF, Natalie, lured me in right from the start of the night and for her, it was like shooting fish in a barrel. Natalie and her husband have all their good friends over any weekend the weather is nice and this weekend was no exception. the only exception was that John was out of town at a court case involving his company and did not come home for the weekend. Natalie, in not wanting to break tradition, insisted that everyone come over, that included me. it started with the text she sent to invite me, it read "johns away, we're gonna play. come over at 330" i was kinda shocked that i received it so i replied, "huh?" she replied with "johns away, people are still coming over." i was kinda disappointed and oddly reassured for the time being. i called my parents and they said they were going over too so then i was more disappointed. knowing that john was away was enticing, but the fact that she corrected her text and invited my parents made me sad. That sadness was almost immediately reversed though upon me getting there. i arrived at about 5 oclock so some of the people, especially natalie, had a major head start on me. when she saw me walking to the front door, she came to the door and said, "why are you late? i was waiting for you." i said, "i didnt realize it was so important. im sorry." she looked perplexed and kind of nudged me out the door to take a walk with her. i followed and when we got to a more private spot, she said, "im going to have my house all to myself tonight and i know you've had a crush on me forever. i want you to stay over and fuck me and i thought you'd want to do that. if ive read the situation wrong, get the fuck off my property and never come back, ill be extremely embarrassed." i immediately grabbed her arm and shoved her back up against the garage wall, i put my right hand on her left breast and my left on the side of her tummy, i looked her in the eye and said, "i never saw this coming. if i thought you were serious on the original text, i would have been here a while ago." with that we kissed and then she pulled back fast saying, "your parents are still here. get them out of here so we can have fun." i went to walk away and she stopped me, reversed position and put me against the wall. she saw i was hard as a rock so she grabbed it, opened my pants, knelt down in front of me and put it in her mouth for 5 seconds. she stood back up and said, "you have no idea what you're in for. ive been planning this since thursday when john told me he wouldnt be done in time. Now go, get your parents out of here, come up with something, ill be around." i waited until my absurdly hard cock went down and then went back into the house to come up with some reason to get my parents out of there. luckily, they were about maxed on the party anyway and told me they were leaving in a half hour or so. that was the longest half hour of my life. nat and i always positioned ourselves at the party so we could see what the other was doing and then, within mins of my parents leaving she texted me saying, "sneak up back steps to my room in 5 mins" I did as she asked, snuck into the room, and there she was, naked on her bed fingering herself. as i walked in the patio doors, i locked them behind me and all but pounced on her. we started with deep french kissing as i slid my hand down her amazingly tight body and into her pussy. the kissing got even deeper and more passionate the deeper i got with my fingers. the deeper i got, the more moist and wet she got and the louder her moaning and sighing got. the louder that got, the more turned on i got, it was amazing. after a while, i sat up and began kissing my way down her body to pussy. i began kissing around the clit to tease her and then, w/o notice, jammed my tongue inside her and immediately tasted her juices. she was moaning so loud i was convinced someone was going to hear us but at that point, with that woman and opportunity, i said fuck it, let them hear it. i went on eating her out. changing patterns with my tongue, fingers, both, she was loving it. i had no idea how much she was really enjoying it until i made one little move with my tongue and she let out this yelp like noise. i thought i hurt her so i pulled my head back fast and right as i did she squirted all over my face and clothing. i had never seen that anywhere but porn before that so i was shocked and dumbfounded, apparently so was she. she said, "ive never done that! oh my god! keep going!" i have no idea how long i was down there but i know that when i finally came up for air, she was so hot and bothered that she couldnt get a word out before she sat up and rammed my cock into her mouth. now, for as good as i felt i did, the blowjob she gave me was otherworldly. she gave me deepthroat, she sucked just the tip, she put my balls in her mouth, she did everything you can imagine and did it better than anything i had ever experienced. as i was getting close to cumming, i let her know by gently tapping on her head. she got what i meant because she nodded her head yes and as she was doing that, i came right in her mouth. she clenched her lips real tight and waited until i was done. when i finally was, she didnt even look up, make a face, anything, she just swallowed and laid back on the bed with her legs up. we fucked in that position, then i flipped her over. since im not the most well endowed guy (6") in the world, the doggystyle position really helped us. i got even deeper and she groaned even louder. thats when we reached our first orgasm. our second orgasm came shortly after when she got on top of me and started riding me reverse cowgirl. that position had the same effect. we tried various other positions throughout the night and completely lost track of the other guests. they had to know what we were doing, but we were both immersed in the most intense sexual experience or our lives. when we finally ran out of gas, we looked at the clock together and it was 130 AM. i asked if i should spend the night and she said, "i'd love a morning delight." i put my head in the pillow and went to sleep.
I was awaken the next morning by her voice. No, she wasnt talking to me, she was talking to john on the phone and i heard her say, "party was great, everyone cut out kind of early so i got a great night sleep." i thought to myself, "that poor guy." she came back to the bed, noticed i was awake, and we fucked one more time that morning. i havent talked to her since saturday but i saw the weather for this weekend and it looks good. should be interesting to see how awkward it is with john home this time.

[niceandspicy]

mmmmm lovely, don't ya just love an older woman :)

[theoldfolks]

Reading your stories is aggravating my carpal tunnel . too many repetitive wrist movements. Thank you.:laugh: