Anne an Old Friend's Mom

Anne was a pretty woman how must have just touched 40 years old when we hooked up. She was definitely a very bangable milf who had a few kids and was going through a hard time. I met her son when I was playing on the travel hockey team. We weren't great friends and didn't really talk, but I had his number in my phone and we were in the some mutual group chats. We hung out in the same group until I went off to prep school for hockey and eventually college.

I took a year in boarding school, then did a year in the ECHL and eventually the AHL before going to my local university. I lived on campus for my first year even though it was my hometown and my parents lived 10 minutes away. I wasn't eligible to play there, but I joined the club team and wanted to get a degree while hooking up with as many girls as possible. Needless to say I was one of the older freshmen in the class so I was cleaning up. The guys liked that I could buy booze and the girls loved that I was older, more experienced, and much more confident.

It was like shooting fish in a barrel. As I progressed, I moved off campus and everyone loved to come to my apartment before hitting the bars downtown. It was called "the pitstop." Eventually I got bored and started to venture off campus a bit I would meet people at the local Applebees and building a network of friends outside of college. I skipped lectures and revision, but always had a 30 rack ready to go.

I first met Anne in the summer before my sr year. We flirted a little at the bar once or twice. It was always in a joking way. She was wearing a ring, but was always with her girl friends drinking. It sounded like she was pretty shy and reserved but I thought she was an easy target. I'm a bit of a taller and stronger looking guy since I played sports. It honestly felt like college or school to me, the girls would almost always be looking for a fun loving jock to entertain them for the night.

One night we got pretty drunk, mostly my fault for supplying the booze.

"Anne, you've got solid knockers." I said pretty matter of factly to her while looking at her boobs. I said it in a way that wasn't aggressive, just a casual acknowledgment.

"Thanks. Pretty direct of you, I must say." She replied with a sarcastic tone to show that she was taken aback by it.

Her thick, dark, curly hair framed her face in a way that made me think about pulling on it.

"Try not to blush too much." I added as a jab while nudging her arm with my forearm.

"I'm not blushing." She said with a pretend annoyance that was cute. She karate chopped my arm playfully. I was flexing and so we shared a look. Her look of surprise that it was hard and my look of "yeah, that's right, I work out" type of thing.

"Look right there, I said as I poked her cheek." Trying to break down the physical touch barrier even more.

"No those are my dimples." She replied while looking away trying to minimize our interaction. I knew I had to say something shocking again to get her attention.

"They say that dimples are just a sign that your parents had sex when you were in the belly. Your dad's dick pokes you in the cheek as he's pumping your mom while your facial muscles are developing." I said as I put my arm around her pulling her close and saying it in her ear in a friendly way. The type of way that indicates this bar is loud and I just wanted you to hear me, rather than pulling her in close in a creepy way.

To my surprise, she stayed in my body space and stood on her tip toes. She grabbed my shirt and leaned to my ear since the bar was loud and said, "no surprise my kids don't have dimples."

"Are you saying your husband has a small weiner and it couldn't reach." Again, purposefully being provocative to keep her attention and move the topic to something sexual. I also love the benefit of putting her husband down too so she would inadvertently think I have a bigger one.

"We just didn't have sex while I was pregnant." She said correcting my assumption with her explanation. I knew I had her.

"So he's got a small peepee and doesn't bend you over regularly." I said again pushing the limits. Then I cut her off when she was going to protest, "or at all. He doesn't bend you over at all." Then I trailed off and said away from her direction almost talking to myself, for comedic purpose, "that man is either gay or has the self control of a monk."

As I kept staring away I could see her pursed lip smile and head tilt. She opened her mouth to say something and I just raised my eyebrows in a questioning manner and she shut it and gave me that pouty smile again.

"Look, I like sex, it's just hard to find time with kids, career, pregnancy, and all that stuff. Not something I would expect you to know about since your like a kid yourself." Anne said trying to sound like we're bantering, but I had her right where I wanted her. She was trying to prove something to me and herself and I struck a nerve.

"Well, you look like you could use another..." I trailed off hoping to get her irritated again.

"No, I don't need any other penises in my life. I've got plenty. Thank you very much." She said sound strong and independent.

"I was going to say another drink. To loosen up. Sheesh. Now I know you NEED another drink." I said to her trying to be funny. I gave the bartend a head nod and held up two fingers. Over she came with 2 more drinks.

"I don't need this. I don't need someone to buy me a drink. I thought you were just trying to say I needed some penis or something else along those lines." She was trying to say, but I stood tall and pretended not to hear her in the loud bar.

I leaned down and told her, "I think I'm getting under your skin a bit, let me buy this a peace offering." Looking defeated and a bit hurt that some random guy her kids age could have this power over her, she submitted and relented to drinking it. That itself was not a sip of alcohol, but a sip of defeat.

"If I didn't know any better, I would assume you enjoy me getting under your skin." I said with some innuendo. Again she punched my arm playfully. We drank and talked and laughed and joked. It was a great night. I noticed her friends were starting to leave and the ones remaining were caught in conversation. It was now or never. I knew she wouldn't leave with me if her friends saw her because then she'd have to explain herself. I took her butt in my hand and jiggled it a bit. She looked at me shocked.

"I had to find out for myself. Nice butt to go along with those tits." I said with a smile.

She didn't have anything to say for a few seconds. "What. makes you. think. you can just grab. a womans butt. out of no where?" She asked.

"That was a grab, it was a jiggle. I'm sorry. I can't help it. It's just very tempting and your hotness overcomes my manners. It makes me uncontrollable. Are you mad?" I asked back.

She breathed audible. I was either about to be kicked out of the bar or I was going to get laid. We looked at each other and she tilted her head while looking up at me. She clinched her jaw in a disapproving manner and I swear she was almost shaking her head.

"You said you don't need to let loose. Prove it." I egged her on.

"My husband is expecting me at 10. You think you're going to just have your way with me in the filthy bathroom or some parking lot?" She retorted almost more trying to figure out logistics rather than making a point.

"No you're a classy lady. I'll take you back to my college apartment." I said as a joke in a manner that she even cracked up laughing. "C'mon, the floor is stickier than here from beer pong, but I just put on clean sheets." I jabbed.

"Oh, so you planned on running in to me and taking me home tonight." She said nodding her head like she was in on the joke.

I put my hand on her lower back and pulled her in. "C'mon, we don't have a lot of time, and you deserve more than 5 minutes. Besides I've been dying to know what a milf taste like after a long day of work."

This did the trick. She looked up at me and nodded. I took her hand and led her to the parking lot. "Wendy drove, so you're going to have to bring me." This was her quiet, tacit way of telling me that I was in control and she agreed to go have some fun with me. The ride was full of sexual tension. It was quiet. I turned the radio off. I slide my hand up her thigh and kept making eye contact with her. As we got to "the pit stop" I fumbled with my keys and opening the door for her.

"Nervous are we? Has it been a while, Mr. big man?" She said teasing me and laughing. As we opened the door I just picked her up and took her straight to my room. She wrapped her legs around me and I pushed her into the closest wall. We started kissing and she was grabbing my hair and squeezing me all over.

I finally threw her on the bed and as she was sitting up, I pushed her back down.

"That was hot." She said out loud.

"Look at yourself. Your tits are already hard as my cock." I proclaimed as she looked down seeing her nipples poke through the shirt. This was a marked change as we've been mostly polite with the occasional butt grab throughout the night. Now I was physically dominant and clearly in control. "I bet your panties have a wet spot where you soaked through already." I said as I used my knees to push her legs apart while climbing in bed.

"I can tell you want them touched, you're just pretending to cover them with your hands. It's okay, I'll have a good look when I pull your shirt off soon." I said in her ear as I leaned my body weight on her. I could hear her gasp and see her lift her chin to embrace the moment. I started to kiss her neck and felt her grip on me get tighter.

"Okay. You with all this cockiness, at least your sheets are clean." We rolled a bit and joked and kissed some more. My hands explored her body and into the waist band of her jeans. I unzipped her and tugged her jeans off. Then I let my face glide on her panties.

"That's right. You're damp and soaked through already." I told her as I stood up and took off my clothes. I worded it in a way to embarrass her a bit.

"I should have freshened up a bit. I can go to your bathroom now if you want." She said nervously, wanting to please me. I love the spot I put her in.

"No, it's what I want. I love the smell and taste of my woman rather than soapy skin." I said again with intention to make her self conscious and to please me.

As she laid back I heard her say towards the ceiling, "You can have whatever you want."

"I want you to touch yourself. Rub that pussy of yours." I said as I took my boxers off.

As I got back between her legs I let my shaft dangle into her thighs. She looked down and then up at me then back down again. The pause was real. Now it was her turn to raise her eyebrows.

"Wait. Okay. Just hold on a second. I'm gonna need a little warm up for that thing." She said giggling.

I just smirked and took her wrist. I guided her hand to my cock and she immediately wrap her hands around it. Like someone feeling a new object for the first time, she wasn't even trying to hide that she wants it now. She let go and propped herself up on her elbows and slid away from me a bit.

"Okay, seriously. Just. You know. Fuck." She exhaled. She took a deep breathe and said, "that's why you're so arrogant, huh? You're packing all that."

"So I'm guessing it's bigger than your husbands?" I said with a smirk.

"I have a toy that's bigger than him, but that is humongus. I need a little warm up. Do you have lube?" She was asking nervously. As she started to rub it again I felt my cock twitch from her talking about my size. I loved every second of it.

As we proceeded to play she took it in her mouth. I kept reinforcing her ability and how good she was which she seemed to like. As she slobbered away, I told her to reach down and play with her pussy. "Now you can really let loose and go wild without worrying about pleasing me or letting it fall out, just bounce as high and hard as you want." I told her as I positioned her body to sit on top of me. She was having a hard time sliding down so she spread her lips and cheeks and kept working it back and forth. Finally I just pushed her down and spread her legs. I could see the fear and panic in her eye. I dumped a ton of lubed on her to get all slippery.

"Let me guess. You don't use lube often?" I asked as she shook her head no. "Everyone thinks it's a lot, but don't worry, you'll like it." I comforted her.

As I put more on, I rubbed in all over her lips, clit, and massaged her ass with it. I could tell she was squirming already. "He's that small huh? Or you get that wet?" I asked.

"No, we just don't have sex a lot. I get really wet so my toys don't need it, but I guess you're the expert with that thing." She said as she stroked my cock to lube it up some more. I pressed my shaft on her pussy and slid it up and down. After a while I could feel her opening up and I pressed my head in her. She let out a loud groan and it was on.

The sex was great, but what happened afterwards made me re-think everything. She went to the bathroom to clean up and came back shocked.

"Wait did you play hockey for North?" She exclaimed more than asked.

"Yeah. Why?" I asked a bit puzzled. I thought I was about to explain to her my AHL career and why I'm here now, but she cut me off and paced around my room a bit. She started to frantically look for her clothes while muttering to herself. "Oh my goodness, I can't believe this. I need to go. I cannot believe this. This is unreal."

"Hey, slow down." I said as I grabbed her arm and pulled her towards me. She yanked it away and kept looking for her clothes. "I'm nervous that maybe you had too much to drink and now you're regretting this. Was sex with me that bad?" I was genuinely puzzled.

"No. Michael. I know you. I. Know. You. I've met your mother. My son played hockey at North. With you. You were on the same travel team. I've seen you play. This is so bad. This is so bad, on so many levels." She was looking for her lingerie, but I could see it was across the room so I got up and get between her and it to slow her down and talk. She couldn't see it around my large chest and frame so I just cupped her and cuddled her.

"It's okay. It's okay." I repeated until she unclenched and relaxed her body a bit. I caressed and stroked her. I played with her hair. I figured it's best to let her talk through it with me rather than make up a crazy story in her head. She saw our championship picture hanging on my hallway wall and it was eerily similar to the one hanging in her house so she stopped to take a longer look. After she realized what it was, she looked at all the other photos. Apparently there are 4 of her son in my house without either of us knowing it.

"Who's your son?" I asked and she replied with his name. I actually knew him. I was a little older, but definitely knew him. "Oh, nice, where is he now, what's he doing? How's he holding up?" I asked to try and get her to talk about something familiar.

"Can we not. Please. Like, can we just not mention him right now?" She protested. As she settled down we ended up with her in my lap and I was massaging her. I ended up gently cradling her down to the bed with me and we laid and talked. I looked at the clock and realized we have 20 mins left before she needs to be home. She also took notice of me clocking the time and started her panic again. I took her phone and put my number in it. I texted myself and told her that I'll take her home and everything will be fine.

I kicked her bra and panties under a pile of clothes and told her that we don't have time. It was part of my plan to see her again. I told her it was more important for her to go home without lingerie. No one will notice since she's covered up in jeans and a shirt. But if she's late then someone will get suspicious.

I got her in the car and was playing with her thigh again. At this point she had calmed down and we were laughing and joking again.

"I'm going to find and wash your lingerie. You can trust me because I have clean sheets. Well, not anymore, but you know I can do a good job cleaning delicates. I'll text you when I find them and will get it returned to you. Promise. I kissed her and pet her body a few times mixed with some squeezes.

"Can you drop me off a few houses down?" she instructed more than asked.

"I'll just pull in. It's no big deal." I told her trying to be a gentleman, but also wanting to get a sneak peek at how she lives.

"I don't want questions. They know this is not Wendy's car. I'll just tell them that she's in a hurry and that was most convenient for her to drop me there." she pleaded and I relented. I reassured her that I don't talk to her son, no one at the bar knows him, I'll never tell him or her husband. I really meant it too. There is no need to do that at all and it's the right thing to do.

As she walked home I got a text. "I can feel your cum dripping down my legs :)"

I went home and smelled her panties. I rubbed them on my face and wrapped them around my shaft to jerk off. I licked it and eventually came in it. It was so hot to think this fabric was touching her bare pussy and now it's touching my cock, lips, tongue, face. I sent her a video of me cumming in her panties. "found them" I said.

"Surprised you still have any cum left after all the stuff that ran down my leg."