Fucking a younger coworker who was 19 years old. He loved my 42-year-old milf body.
We both work part-time for a small mercantile downtown. A friend of mine owns it, so I like to help out a couple of nights a week. This guy, we’ll call him Jacob, is super sweet and is going to college and does this for a little money. He had been stressed out with finals going on and was down in the dumps because his girlfriend decided she didn’t want to see him anymore. To top it off, a rude customer kinda ruined his evening. After they were dealt with, I had a little plan.
We had harmlessly flirted a bit with each other over the last couple of months. So after we closed I told him I had a Christmas gift for him in my car. We trek out to the parking garage. As we get to the back seat, I lean against the car and ask him point blank if he would like a blowjob. The poor guy was awestruck. He stammered over his words for a moment before nodding yes. I open the back seat and motion for him to climb in.
I pull my top and bra off as we settle in, and tell him he can play with them if he wants. His hands are hungry, pawing, squeezing, and flicking my nipples. He enjoys himself greatly before I start tugging at his slacks to pull him out of his underwear. It’s a pretty nice cock, thicker than average and made me wonder how it would feel inside me. I start to work on his cock, giving it 100% to blow his mind.
He didn’t last two minutes.
I swallowed every last drop until he was dry and begging me to stop from overstimulation. The garage isn’t busy, but the tinted glass keeps us mostly hidden. His mouth falls to my chest, however, and he’s not done with me. So I give him better access while he worships me like a goddess. It’s not long before he’s starting to swell up again, so I lower my mouth to his tip and swallow him whole.
He lasted a bit longer this time. Maybe five minutes or so. After he gave me what little seed was left, I told him to pack a condom next time to get the full experience.
The next morning after our fun in the car, he almost immediately messaged me asking if I was serious about a follow-up with a condom. Seriously, it was 7:42 in the morning. It was cute, and I told him that I was. I wanted to be his little Christmas present this year. One that he’ll always remember. He confessed he was still a virgin and wanted to know if that was okay. Again, cute. I told him it was, and that since I had my tubes tied years ago that if he will go to the student clinic on campus and got an STD test, we can forgo the condoms.
I pulled out all the stops for this. The mercantile we work at is in the downtown portion of our city, and there’s a pretty nice hotel a couple of blocks down. I rented a room for the two of us. Got freshly waxed all over, made dinner reservations, and picked out a little lingerie for him to enjoy. If he is going to have a MILF, he’s going to have the time of his life. Messaged him the details and to pack an overnight bag for after work Thursday. He agreed, and our date was set.
Work was excruciatingly long for both him and me. It’s all I was able to think about for the last few days, and this little shift was taking forever. The casual glances knowing what would be happening in just a few hours. Noticing that his slacks were tighter than usual. It makes a woman hot and bothered! 6:30 couldn’t roll around fast enough. I swear we were running out the door as soon as we clocked out.
We checked in at the hotel, and then made our way up to the floor we were staying on. He’s shy and he’s really sweet. His eyes are on me the entire time, and it’s like his cheeks are a permanent rouge. Once we’re in the room, I tell him I need to change quickly before we go to dinner. I slip into the bathroom to change into my lingerie (a cute combination of a see-thru mesh and lace bra, g-string underwear that has a little slit at my entrance so I don’t even need to take them off, a garter belt, and thigh high stockings) with a navy blue dress over top. You can certainly see my hard nipples through the dress, which is a selling point, especially for my date.
He’s speechless as I walk out. His jaw hits the floor, and his brain is working 3 frames a second right now. I ask if I look alright, which can only be answered by a nod, so I walk over and kiss him softly to ask if he’s doing alright. I think the kiss helped because he started acting more himself afterwards, and dinner was lovely. Fun, light, great conversation. He’s such a lovely young man.
We make our way back to the hotel room after dinner, and the moment we get into the elevator, I take his hand and guide it to my chest letting him feel it. His large hand paws at me through the dress while I whisper “all of me is yours tonight.”
We’re practically running to the room now. I guide him to the section along the wall once we get in, and gently push him onto the seat while I step back to give him a full view. I ask if he would like to receive his Christmas gift a little early. The dress drops from my body to reveal the lingerie underneath, and I swear his eyes light up like it’s Christmas morning. I can see him through his slacks, a very distinct outline of his cock pressing tightly against the fabric as he takes all of me in.
I step toward him slowly before dropping to my knees in front of him. My hands word deftly on his belt and then to his pants themselves, pulling them down to release his throbbing manhood. He loses the pants completely until all that’s left is his cock stretching upward, throbbing. Fingers run along his thighs as I lean forward and take him into my mouth like I did a few nights before.
Except I wanted more. I only bobbed my head a few times until his length was nice and wet. I then stood up, and climbed on top of him, straddling his hip with both of my knees. He’s quite a bit taller than me, but, here, it’s the right angle to kiss me or suck on my tits. It’s perfect. I ask if he’s 100% sure he wants to lose his virginity like this, to which he nods, so I tell him to sit back and relax and let me take care of him.
I take his cock into my hand and guide it to my entrance. He’s not a pornstar by any means, but while he might be average in length, his girth is incredible. My husband is pretty big, yet this is even thicker. His head starts to part my bare lips, and once the tip is seated, I rest my hands on his shoulders before lowering myself so he can impale me.
I’m not quiet. I can’t be. He’s stretching me open unlike I’ve ever been, and it feels beyond incredible. It takes probably 15 seconds before my lips wrap around his hilt. I’m shaking uncontrollably on him. My muscles keep squeezing around his cock, trying desperately to find any sort of normalcy, but they find none. We sit there for many moments trying to adjust to each other, all the while his fingers dig into my hips and thighs making beautiful little bruises later on. Once I find a little composure, I start to grind a bit on him, and then maybe a minute later, I’m loosened up enough that I can start riding him.
It’s slow and steady. Sweet and cute. I’m riding him like a good cowgirl would, kissing him every few seconds, but I know a face that’s trying not to cum too quickly. He’s struggling. So I whisper in his ear that it’s okay if he needs to cum. That I want him to cum in me. I’m bouncing on his cock, in lingerie, with a tight pussy he can freely cum in. He grunts loudly, and I feel the splash as he cums hard, shaking under me as he unloads what I’m sure was days worth of cum.
I slowly ride out his orgasm until he starts to wail from oversensitivity. However, I don’t slide off him. I keep him buried in me and start making out with him. We kiss hard, his hands wander, treating me like a goddess while he’s still connected to me. He never fully softens, and with a few minutes of hot and heavy make out, I can feel him harden in me again. His hips start to grind, and soon he’s fucking me now.
I reach around and undo my bra, throwing it to the side so he can have full access to my chest. He’s more aggressive now with hands cupping my tits, mouth reaching down to suck my nipple. I’m moaning like a whore without a care in the world. I can hear how wet I am with every smack of his lap into mine. We’re both soaked. I push him back into the couch, taking control as I ride him now, but much faster than before.
My tits are in his face as he takes another one back into his mouth which does me in. My nipples are incredibly sensitive, and with his cock stretching me open like this, I cum hard on his cock. I’m shaking, almost screaming his name, while he slowly slides in and out of me with his lips kissing my neck and collarbone. This is many moments before I am even functioning again. I feel exhausted, but without saying a word, his hands are on my back, cock still in me, and he lays me down on my back with him on top.
I tell him that I’m all his. That he can do whatever he wants. He nods and starts fucking me again. His hands are all over my body now. He’s exploring every inch while thrusting. It’s an awkward pace since it’s his first time, but he’s doing the best for himself. I reach out and play with his chest hair while my legs wrap around his hips. I’m begging for him to cum in me again.
He speeds up inside me, but I tell him to slow down for just a moment. I work my left leg up from between him and the cushion and hook it above his shoulder so he can get deep in me. His strokes turn longer, harder, faster. He lasts maybe another 45 seconds before I could see it written on his face. He cums again in me, grunting louder than last time, and slamming his manhood into me. It’s glorious, and he looks incredibly relaxed afterwards.
Once he’s fully drained, I lean up and give him a deep kiss. I tell him how wonderful he did, and how amazing he felt. He finally slips out of me after a few seconds. I shudder from feeling so empty now. It’s an awful feeling. He collapses back against the couch, so I head to the bathroom and come back with warm clothes to clean him up with. Then, I stripped completely and told him that for as long as we are in this room, he can do whatever you want with me. I’m his MILF.
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