Erin Filling the Gap Ch. 01

For those that aren't familiar I (32M) had a MILF FWB named Kat for about 8 months who was a coworker of mine. During that time, she introduced me to her best friend Erin (44 MILF) who we had a couple of threesomes with and I have hooked up with just me and her twice.

Anyways, Kat and I ended things when she met someone, but Erin and I have still hooked up a couple of times, but this is the first one worth writing down.

Erin is a successful lawyer who does a lot of work with charities since she is divorced, and her kids are both in their late teens. One of these charities is a foster group that is very large in our area and state. I am a teacher, so I was familiar with the group, and with Covid numbers and restrictions easing, the charity planned to have their annual gala/event/dinner, whatever you want to call it.

Erin asked me if I would attend as her date because I knew the organization and I could talk about what it had done for the kids to people there. I agreed and seeing it was a formal occasion, I rented a tux and headed to Erin's house to pick her. Seeing as the event was at a nice country club, we had preplanned to take Erin's BMW rather than my truck.

When I got to Erin's I knocked on the door and she yelled from inside "Come on in Jack!"

As I walked in the house Erin was just coming down the stairs. She had on a green floor length formal dress with a slit to mid-thigh and just enough of a neckline to show some subtle cleavage (For those who haven't read earlier stories, Erin is 44, with a great "mom ass" and a set of natural 36D tits that have only sagged a little after kids.).

As she reached the bottom of the stairs I remarked, "You look stunning Erin."

She smiled and responded, "Well thanks Jack, you don't look half bad yourself. We had better get going so we aren't late; you can drive".

I won't bore you with all the stuff from the next 2 hour, but basically, we got to the party, got drinks and mingled where Erin introduced me to people and I talked about what the program was doing for kids in our area.

After dinner there was more drinks, talking and then dancing. I pulled Erin away from her friends and asked her to dance.

As we began to dance, we caught up on the evening so far and she goes "Thank you for coming, the people you've talked to seem to have responded to your firsthand knowledge."

I responded, "No problem, I'm glad I can help, plus I get to see you in that dress, so it's a win for both of us!"

She laughed and playfully smacked me on the shoulder.

I responded, "What?! You look sexy as hell and I know you're not wearing panties because that dress is even to tight for a thong."

She giggled and said, "You caught me." We danced a few more minutes as the song ended and she said, "I need a drink, but meet me in room 201" in five minutes, its upstairs." I got a grin on my face and nodded.

After waiting 5 minutes, I grabbed a drink and walked off like I was going to the bathroom before making a quick turn and heading up the stairs. As I reached the end of the hallway, I came to a smaller dining room numbered 201.

When I pushed through the door, I could see the glow of a cell phone flashlight in the corner and made my way there. When I reached the corner, I found Erin sitting in a chair with her dress hiked up around her waist, slowing fingering herself.

I laughed a little and said, "I knew there were no panties."

She responded with, "I told you there weren't but hearing you say you caught me turned me on. I need you now."

I stepped towards her and replaced her finger with mine; I could tell she was soaked.

She then moaned softly and said, "We don't have time for foreplay, I need you to fuck me now!"

I wasn't going to ask questions, I just said, "Stand up, turn around and bend over that chair."

Erin did as I told her, and I dropped my pants to the floor and slid my cock into her pussy. I'm average length but have decent girth, but no matter what, anytime I slid into Erin, she always moaned and said I fit her perfectly.

I started to slowly thrust into her causing her to moan, I kept up the steady pace as I felt Erin shift a bit so she could rub her clit while I fucked her. Her moans became louder and breathing shallower as I increased my pace.

I could feel her getting close and then her pussy clenched my cock as she began to cum. I kept pumping through her entire orgasm but as she relaxed, I slowed down.

She caught her breath and said, "Thank you so much for that, now it's your turn, give it to me hard and fast."

I said, "Do you want me to cum in your mouth?"

She answered, "No, can't risk it on my dress, fill me up." I began to fuck her hard and fast as she requested and after about 2 minutes, I felt my balls tighten as I dumped my load deep in Erin's pussy.

As I came down from my high and slid out of her, she got on her knees in front of me and goes, "That's a good boy." As she proceeded to clean our cum off my cock with her mouth.

As she finished cleaning me up, she glanced at her watch and goes, "Oh shit, we've been gone 20 minutes, we need to hurry back!"

We both straightened ourselves up, finished my drink that I had brought then went two separate ways back downstairs to the party.

Over the next hour and a half, I only saw Erin across the room and the whole time all I could think was, "Damn she didn't clean herself up, my cum must be running down her leg unless she went to the bathroom."

That thought was enough to keep my cock semi hard for the rest of the evening, thank god for looser fit pants. As it got to be around 11pm, the party wound down and

Erin found me and said, "Well Jack, are you ready to leave?"

I responded, "Whenever you are, let me grab our things".

After I had retrieved our stuff, I met Erin at the front doors and made our way to her car.

When we reached the car, my previous thoughts were confirmed when Erin said, "There is a blanket in the trunk, grab it for my seat, don't want your cum staining the seats."

I laughed and got her the blanket then held the door open for her.

When I got into the car and pulled out of the parking lot, Erin said, "Thank you for a great evening and a great quickie, you came so much."

As I looked over to smile and say thank you, Erin shifted and pulled her dress up and I could see where my cum had run down her legs and she spread her legs so I could see her pussy.

Erin has always been the wettest women I have been with, but her wetness mixed with my cum left her pussy looking absolutely amazing.

I just remarked, "Wow"

She said, "See what you did to me, I've felt this for the last 2 hours and I keep getting hornier and hornier! I thought the quickie would fix it."

I reached over and began to stroke her outer lips feeling the stickiness of both of us as I drove. As we got closer to her house, I said, "If you want, I can stay over and help you fix your little problem?"

She said between sighs, "Thank god I thought you'd never ask!" We pulled into her driveway, I quickly shut the car off and we practically ran into her house.

As we got inside, I shut the door with my foot and shoved her into the living room. She turned around and said, "Get this dress off of me!"

I unzipped the dress to where she could reach it and we both began to shed our clothes. By the time I was naked Erin was left in her heals and bra. As sexy as it was, I had to have her tits. I pushed her onto the couch and then unhooked her bra, throwing it into the pile of clothes and latching onto her nipple while cupping the other one.

As usual this caused her to moan louder and louder, especially when my hand left her breast and slid two fingers into her pussy. Due to her wetness and my cum, they slipped in with no resistance whatsoever.

As I began to finger her more, aiming for her G-Spot, Erin goes "Oh god yes!" I kept this up for another minute or so and I felt her pussy clamp on my hand as I felt her orgasm, then the satisfying feel of her squirting all over my hand and arm.

I slowed down and let her relax and she goes, "Thank you so much, now let me have that cock." Erin stood up as I sat on the couch; she got down on the floor and proceeded to take my whole cock at once.

Erin probably gives the best blowjobs I've ever had; they are just the right amount of sloppy and she cups my balls perfectly. Like always with her after 5 minutes or so I had to stop her.

As she pouted " I said, "If you want me to fuck you, you have to stop."

Erin stood up and as she straddled me goes, "Actually I'm going to fuck you." She slowly lowered herself onto my cock with a sigh. She started to slowly grind her hips into mine. I grabbed her hips and had her speed up a little bit.

Once we had found a rhythm we both liked, I reached my hands around and grabbed her full ass. As Erin began to work up a fast pace, I buried my face in her tits, kissing ang biting them before moving onto her nipples, causing her to moan.

We kept this up for about 5 minutes and we were both getting close and running out of breath; I shifted my hips a little bit which must have changed pressure on Erin's clit because she suddenly moaned, "Oh god yes!" She sped up her pace as I Stayed still when she slid up on my cock and slammed back down.

I felt her pussy walls begin to clench which sent me over the edge. I shot 3 or 4 ropes deep into her pussy as she ground her pelvis against me and screamed as she orgasmed.

She collapsed against me as we both regained our breath. As my cock softened inside of her, she picked her head up and goes, "That is much better, being quiet before sucked."

I just laughed and said, "I agree that was a lot more fun."

She stood up and said, "Would you like to spend the night?" I agreed and said, sure, but let's shower first, no need to trash sheets." We went upstairs to her bedroom and cleaned each other off in the shower before heading to bed.

I woke up the next morning by myself in bed but found a note on the door. The note read, "Come on downstairs I'm out back in the hot tub if you want to join."