In praise of MILFs

#44
Last night was a free night feeling the need for some fun me and couple of buddues go MILF hunting we end up at Tiki lounge in Patchogue on the water. While scoping the place out we see about 4 women sitting alone at a table I have my eye out on one then she gets up walks to the bar I go over and start talking to her senseing I am getting in I ask if she wanted to sit and talk she goes over to friendsand let them know we grab a table we order something to eat her another drink ( I do not drink when I drive) start talking finds out she is divorced and has a small child and lives i basement apartment with her sister and family. Getting late asked if wanted to go somewhere else and be alone she calls her sister and says she can t make it home staying with a friend we go back to my apartment. After a nice amke out/petting session on the couch and ask her if she wants toget more comfortable she starts to get shy we sit awhile longer she get up goes to powder room comes out stops at the bedroom I get up lead her in. She drops the bomb and said it has been a long while so I take it slow make sure she has atleaset three before I go in. I take out a cover she puts on get in the mish and start slow after awhile she loosen up gets n the cg position and rides.we rest some relax n the hot tub start all over again spends the night I wake up to nice to nice bj when done i aksi she wants something to eat she sayswants to get home before her daughter wakes up she just left got her number and will be on the rotation...
 
#45
Are the women ever solo? Or do they always do it in groups? I'd probably do it solo and thinning their groups sounds like it could be tricky.
 
#46
Last night was a free night feeling the need for some fun me and couple of buddues go MILF hunting we end up at Tiki lounge in Patchogue on the water. While scoping the place out we see about 4 women sitting alone at a table I have my eye out on one then she gets up walks to the bar I go over and start talking to her senseing I am getting in I ask if she wanted to sit and talk she goes over to friendsand let them know we grab a table we order something to eat her another drink ( I do not drink when I drive) start talking finds out she is divorced and has a small child and lives i basement apartment with her sister and family. Getting late asked if wanted to go somewhere else and be alone she calls her sister and says she can t make it home staying with a friend we go back to my apartment. After a nice amke out/petting session on the couch and ask her if she wants toget more comfortable she starts to get shy we sit awhile longer she get up goes to powder room comes out stops at the bedroom I get up lead her in. She drops the bomb and said it has been a long while so I take it slow make sure she has atleaset three before I go in. I take out a cover she puts on get in the mish and start slow after awhile she loosen up gets n the cg position and rides.we rest some relax n the hot tub start all over again spends the night I wake up to nice to nice bj when done i aksi she wants something to eat she sayswants to get home before her daughter wakes up she just left got her number and will be on the rotation...
How is that place? I live not far from there but never went in.
 
#49
The owner is a swinger himself, I used to do some work with him and the marina. Horrible business owner /partner, goes through 2-3 bar managers a year cause he doesn't know what he is doing.
 
#53
Interesting turn of events yesteday. Had to get my insurance straightened out. Long story short was in their office for quite some time. Started small talk with one of the employees. One thing led to another and at one point told her in passing that she was gorgeous and then let it go. Talked some more about nothing. She was pleasant to talk to and when I was leaving I went to say goodbye have a nice day and in passing said I should call you about something we were talking about. She said then why don't you. Got her number and left figuring it wasn't her number.

About an hour later messaged her that "I enjoyed our talk and enjoyed seeing you. Let's follow through as discussed." Messaged up a meeting time although neither one of us mentioned any details about what we'd be doing. I pick her up later and say where would you like to go figuring I wouldn't get much further than dinner at a diner. Turns out she did her self up real nice and also had gone and picked out a hotel. I said that's nice but it was too far away so did some quick finger work and ended up at a nice place a few blocks away from her.

We talk in the car and find out she's 25 and has a 4yo. Finally get to the hotel and she's nervous as hell. So I tell her let's just talk. Between getting stuff from our coats and going to the bathroom we eventually move from sitting in chairs to sitting next to each other on the bed. She's telling me about how stressed out she's is especially taking care of her kid. I'm checking her out like a perv with no reservation whatsoever. She picks up on it. We then start touching each other as we're talking. Eventually she kisses me on the lips.

I tell her lay down and I'll massage you. Next things she's in bra and panties. I pull her over and start kissing her chest. She takes off her bra and let's me play. She then asks if I have condoms. I say yes. She like I want to get on top of you. So much for her massage.

She's attractive and must get guys hitting on her all the time but she claims she hasn't fucked in about a year and is horny as hell. She's trembling on top of me. She's so horny she can't even put me inside of her. Took about 5 minutes to get her to calm down as I'm trying to avoid her snapping my dick in half everytime she misses. Finally grab my dick with one hand and her shoulder on the other and tell her calm down we have all night. Finally get inside her but she's bouncing like a movie sped up and it's not working. She's then like fuck me doggy asking me if I know what that is. Um of course!

We flip and instead of letting me fuck her she's fucking me backwards doggy. Pounding and positioning herself to feel it. She cums twice but it still really isn't working for me. She just wants cock inside her and humping just to hump and feel it erratic as hell like she's getting a fix. By now she's wet everywhere not only pussy but she's glistening arms, legs and back from sweating.

She finally realizes this still all isn't quite working for me so she gets on her back so I can fuck her mish bringing her legs back to let me pound her. She then pulls me to her lifting her head and wants to kiss. She now I'm pounding her while making out like crazy. I haven't gotten to do that in a long time. She can barely breathe out of breath but wants to keep kissing while fucking.

She cums a few times and I tell her I want to watch her pretty face suck me off. She puts her hair in a scrungy, gets between my legs, sticks her ass up so I can see, and goes to town jerking and sucking I really liked her give extra by pushing her face balls deep every few gulps. Wouldn't let me cum in her mouth, but there you have it.

So here I am on SA looking for attractive 70yo MILFs lol and this one drops from the sky. She was fit and tight as hell and if she hadn't told me I wouldn't have known she had a kid. I always thought I'd position such as in real life experience as girlfriendy if it ever happened but I told her as we were leaving that I'd give something and did. Hoping to meet her again Friday! But if she just used me to get off and she does this all the time I'm still a happy camper!
 

billyS

Reign of Terror
#54
Interesting turn of events yesteday. Had to get my insurance straightened out. Long story short was in their office for quite some time. Started small talk with one of the employees. One thing led to another and at one point told her in passing that she was gorgeous and then let it go. Talked some more about nothing. She was pleasant to talk to and when I was leaving I went to say goodbye have a nice day and in passing said I should call you about something we were talking about. She said then why don't you. Got her number and left figuring it wasn't her number.

About an hour later messaged her that "I enjoyed our talk and enjoyed seeing you. Let's follow through as discussed." Messaged up a meeting time although neither one of us mentioned any details about what we'd be doing. I pick her up later and say where would you like to go figuring I wouldn't get much further than dinner at a diner. Turns out she did her self up real nice and also had gone and picked out a hotel. I said that's nice but it was too far away so did some quick finger work and ended up at a nice place a few blocks away from her.

We talk in the car and find out she's 25 and has a 4yo. Finally get to the hotel and she's nervous as hell. So I tell her let's just talk. Between getting stuff from our coats and going to the bathroom we eventually move from sitting in chairs to sitting next to each other on the bed. She's telling me about how stressed out she's is especially taking care of her kid. I'm checking her out like a perv with no reservation whatsoever. She picks up on it. We then start touching each other as we're talking. Eventually she kisses me on the lips.

I tell her lay down and I'll massage you. Next things she's in bra and panties. I pull her over and start kissing her chest. She takes off her bra and let's me play. She then asks if I have condoms. I say yes. She like I want to get on top of you. So much for her massage.

She's attractive and must get guys hitting on her all the time but she claims she hasn't fucked in about a year and is horny as hell. She's trembling on top of me. She's so horny she can't even put me inside of her. Took about 5 minutes to get her to calm down as I'm trying to avoid her snapping my dick in half everytime she misses. Finally grab my dick with one hand and her shoulder on the other and tell her calm down we have all night. Finally get inside her but she's bouncing like a movie sped up and it's not working. She's then like fuck me doggy asking me if I know what that is. Um of course!

We flip and instead of letting me fuck her she's fucking me backwards doggy. Pounding and positioning herself to feel it. She cums twice but it still really isn't working for me. She just wants cock inside her and humping just to hump and feel it erratic as hell like she's getting a fix. By now she's wet everywhere not only pussy but she's glistening arms, legs and back from sweating.

She finally realizes this still all isn't quite working for me so she gets on her back so I can fuck her mish bringing her legs back to let me pound her. She then pulls me to her lifting her head and wants to kiss. She now I'm pounding her while making out like crazy. I haven't gotten to do that in a long time. She can barely breathe out of breath but wants to keep kissing while fucking.

She cums a few times and I tell her I want to watch her pretty face suck me off. She puts her hair in a scrungy, gets between my legs, sticks her ass up so I can see, and goes to town jerking and sucking I really liked her give extra by pushing her face balls deep every few gulps. Wouldn't let me cum in her mouth, but there you have it.

So here I am on SA looking for attractive 70yo MILFs lol and this one drops from the sky. She was fit and tight as hell and if she hadn't told me I wouldn't have known she had a kid. I always thought I'd position such as in real life experience as girlfriendy if it ever happened but I told her as we were leaving that I'd give something and did. Hoping to meet her again Friday! But if she just used me to get off and she does this all the time I'm still a happy camper!
May I ask how old you are and if you look your age?
Sounds like quite a score, a 25 year old.
 
#55
May I ask how old you are and if you look your age?
Sounds like quite a score, a 25 year old.
I try not to say much about myself here. But I'll say that apparently I don't look my age but maybe not the way you're thinking as with most people it would be you look younger but many people think I look younger AND older. I don't understand it so can't explain it. Enough said.

As with all things got to just take their word for it. For all I know she has no kid and is ... could be.. I'm guessing up to 32. And the more I think of it the more I wonder if I got duped or whether I'll ever be able to see her again as the more I think about it the more I wonder if she wasn't on something.
 
#56
I try not to say much about myself here. But I'll say that apparently I don't look my age but maybe not the way you're thinking as with most people it would be you look younger but many people think I look younger AND older. I don't understand it so can't explain it. Enough said.

As with all things got to just take their word for it. For all I know she has no kid and is ... could be.. I'm guessing up to 32. And the more I think of it the more I wonder if I got duped or whether I'll ever be able to see her again as the more I think about it the more I wonder if she wasn't on something.
I was thinking the same... @billyS question...

I don’t quite understand this response
 
#57
I was thinking the same... @billyS question...

I don’t quite understand this response
I got lucky there is no doubt about it. 3-4 years ago I had so little game I probably could not have coaxed even the most lonely woman to even talk with me. Most of my SB have been 25-30 so I've been able to boost my confidence immensely since, figuring out how to say things, not say things, timing, etc. In short, I learned and learned well.

I'm not going to post my age. Some people way underestimage my age and some people way overestimate my age. What can I say I'm a chameleon.

To me she didn't react perfectly normal. Maybe she was just excited maybe something else (stoned I'm guessing). And I thought she could have been older than she said she was. For all I know she's just a SB telling me what she thought I wanted to hear. I'll find out more if I can seal a second date.

Anything else well the Senate said no witnesses
 
#58
Got to see my MILF again during wee hours this morning. Her personality is more dizty than I realized which is why I wasn't sure she was stoned or not and in fact I'm still not sure either time atop it. Not sure how she keeps her job unless this is an act and now even wondering if she put herself out there for me in the office now that I replay it all. Anyway ditzy seems to come up often enough in my non-milf endeavors don't know if this is a character trait or just random or not.

She definitely has a kid as she got a call from her mom mid-coitus that she took I probably would have too so ok with that. Still thinking she's older than she's saying but not caring at this point.

Sex went smoother this time no broken penis attempts so guess she was just excited to get laid in such a long time the first time. Did the usual standard acts. But at the end told me she wanted to thank me for giving her cash last time. So she sucked my cock like an animal for about 20 minutes. No real DT this time but definitely had an outer body experience watching her waiting for her head to fall off going to town I really appreciated her doing this. Some women have done this for a few minutes but 20 min like a machine a fucking champ for sure. I was already emptied by this point so this was just to enjoy the sensations of the act and the live performance with my mouth hanging open. She then got on top of me and we made out for a few minutes. And of course this sealed the deal that I gave her cash again this time.

Don't know how long this is going to last and feeling more SBish than MILFy but going to view each meeting as a life bonus. And if it stops can't complain.
 
#59
I have been lucky with the MILFS I have been meeting up with had a few that lasted years the current one is going on 2 years but is ending due to her husband getting a job transfer But I just meet another one who just happens to be a 3rd cousin which I talked about in another thread. I have always had a thing for older women (before the term MILF was around) ever since I was teenager
 
#60
I remember it dawning on me in first grade that I loved the girls in my class and woman. Around first or second grade obtained a steady source of magazines and looking at grown woman naked had me hooked even though I didn't really grasp sex and erections and such fully yet. By 3rd grade was conscious that I was checking out friend's moms. From that point on family and friends parties and the beach and pools and other such gatherings was a pure joy. Can still remember the first time I jerked off. Reading things like Penthouse Letters I kind of never believed even though I was so young and whether they were made up or not it all seemed like unicorns but now feel like somehow I'm now living some of those scenarios the past few years. I still want a much older woman so need to figure that out still lol
 
Top