Dirty Diego

My name is Diego and I've had some wild good times. I'm now in my 40s and lately I've been thinking back to all the crazy shit I've gotten into. I want to make sure I can come back and revisit these memories in all their glory so I've decided to write them down. Why post them here? A few reasons:

1. It won't be on my computer where someone can find it (especially my wife and nosy kid lol)

2. I can access from anywhere.

3. It's unlikely anyone I know will be able to find my stories here since this site has so many.

4. I've been jerking off to these memories so why not let others do it too lol.

With that out of the way I'll start with the summer before college. I worked my ass off in high school and focused that summer on making all the extra cash I could. I'm talking valedictorian, sports, community service, all the things that look good on a college application. I came from a lower middle class family and had aspirations of something bigger. Nothing against my upbringing, they did the best with what they had, but I wanted the life of white people old money if you get what I'm saying. So I thought the best way to do that was to marry into it. Yeah, while my peers were having a social life and having fun I was working my way to a good school where I'd have the chance to meet a rich girl. Totally a gold digger and I'm not ashamed to admit it lol.

Sure I had girlfriends but I only really hung out with them if I knew I had a chance to get some action. I had long term priorities so it needed to be worth my time lol. It's no secret that guys have high sex drives but mine has always seemed to be on overdrive. That was the problem with girls that age, they didn't want to fuck you unless you were dating them. But I'll admit I looked fucking good from face to body, I have a way with making people comfortable around me and my record seemed clean so they let their guard down. Parents fucking loved me lol.

Anyway that summer I held on to my then girlfriend telling her we'd stay together even when we went to college just so I still had access to reliable pussy. I had saved up a ton of money in high school doing odd jobs for the rich people in a nearby community and continued those jobs during the summer to squeeze out some extra cash. If I was going to marry a rich girl I'd need to be in a frat, and those don't come cheap!!!!

This one couple I worked for that summer hired me to do odd jobs around the house and I learned a lot about home maintenance. The husband would go to work and it'd just be me and his wife though she mostly kept to herself doing who knows what. But sometimes we'd chat or she'd tan out by the pool in a skimpy bikini. I'd say she was in her early 30s with the kind of body you'd see in a nudie mag and the kind of face that makes you do a double take. They let me use their pool whenever I wanted so I usually worked in swim trunks which allowed me to jack off from a window to her full breasts and tight bottoms while she had her sunglasses on lol. They were short trunks not the usual ones that go to the knee so it was easy to take my dick out from the leg hole and stroke it. Made it easy to put away too just in case. I think you can see why my nickname is Dirty Diego or Dirty Deeds as some friends call me.

Those tits man. They were full enough to look fake but the way they moved you knew they weren't, and the size was just a little too big but still believable for her skinny but still curvy body. Sometimes I'd grab some of her silky lingerie to fuck my dick with while I imagined what her tits looked like bare. I wanted to see her naked so bad it made me nut fast every time. I imagined the triangles of her bikini top spread to both sides so I could blow my load all over each tit and spread it around with my dick all over those nipples lol. Sometimes I'd imagine cumming on her fake tanned face, sunglasses, and bleach blonde hair. When I felt really dirty I'd imagine her bottoms off so I could cum on her pussy and use my dick to push it into her hole. Almost got caught one time when her husband came home too quietly lol. Accidentally got some cum on her panties in the panic but I had no time to clean them so I just stuffed them in my pockets. I liked having them to jerk off in at home so I never returned them.

I think she noticed they were missing because from then on she spent more time where I could see her and her outfits got more bold. She also started to walk with a sexy sway to her hips that never failed to get me hard. The first time she noticed the effect she had on me was because I'd tried to contain my hardon with the band of my trunks but my dick is a little too long so the head popped out and said hi lol. I pretended not to notice but it turned me on so much that she saw. She blushed and looked away but I saw that huge smile lol. Her nipples got rock hard and she went to her bedroom. I like to think she went to touch herself, I didn't see her again before I left for the day.

I got a little bold from that encounter and let my head peek out just a tiny bit every once in a while. I could tell she loved that so I gave her plenty of opportunities to sneak a peek at it. She'd hang out with me in the house and we'd chat for a bit then she'd lay on her stomach on her lounger by the pool with her hand under her and I knew she secretly touched herself. I liked to talk with her in the kitchen when I went for a glass of water so I could sit on a counter chair because it made my dick stick out even more. I could even get my sack to hang out a bit if I made the right motion. It's a perk of having big balls lol.

Remember I still had a girlfriend? I loved edging myself to this hot older woman when I knew I'd be seeing my girlfriend later because I'd put my girlfriend on her stomach as if she were my employer on her lounge chair (honestly can't even remember this woman's name anymore) and imagine I was fucking her instead. That was the best sex I'd ever had with my girlfriend and I'd cum so fucking hard. She thought it was because I was going to miss her when we went to college lol.

About a month in I realized I'd be off to college soon so I'd better try and amp up what I could get away with while I had time. If I fucked it up I already had just enough to cover frat costs so I figured I didn't have much to lose.

Instead of tucking my dick in the band I started letting it hang to the side of the trunks so if I bent over or sat down she'd get a good eyeful. All of a sudden the sink started "having problems" so I'd be on my back with my knees up, feet on the floor, and the air on my fully exposed dick while she went on about how inconvenient it was that there were so many problems with it and I pretended I was doing something lol. That lasted a good few days.

It finally came to a head (lol) when she asked me to rub some sun tan lotion on her back one day. I tried to sound casual when I said "sure" but it totally made my dick bob and let out a little precum. She laid on her stomach on the lounge chair as usual and I swung my leg over to straddle her back so I had better access. She undid the string to her top so the sides fell and I had an incredible view of her breasts squished out on both sides. I was mad horny at this point and figured since she couldn't see me I'd somehow try to finally get my dick to touch her. I adjusted my trunks so my dick was fully out and decided to scoop my balls out too. Didn't want them to miss out! I was giddy with excitement at this point and more precum came out. I sat on her lower back and immediately felt bliss because my nutsack was on her warm skin. I almost sighed out of contentment and blown my cover. God how I'd love to just live with my nutsack on her all day.

I'd never seen my cock produce so much precum, it started dripping too low and I was worried she'd notice it pool on her back before I'd even opened the lotion. I quickly squirted some lotion into my hands and squirted a little on my dick too. It needed touch so bad at this point that the cool lotion made it start drooling even more precum. I gave it a good firm stroke from base to head to wring out the stuff still in my dick which was when it finally hit her back and she jumped a little. The movement pushed my ballsack harder against her and the stream of precum thickened. She said something about her back tickling so I apologized and set to work with a devilish grin.

It was so fucking sexy rubbing her back with my cock and balls out. My dick wasn't on her yet but it was connected to her by a healthy stream of precum that I didn't let fall from the head. Under the guise of wanting to be thorough so she didn't burn I prolonged the rubbing and added a little massage to it so hopefully she'd let me stay there longer. Every few strokes on her back I'd stroke my cock too. She let out the sexiest fucking moans and complimented my technique. In order to reach her shoulders I leaned forward and my cock was so close now it could feel the heat radiating off her skin. I realize how stupid it was now that I thought maybe she wouldn't notice but I finally adjusted my position and leaned far enough forward so my dick touched her skin.

After all that time wishing for that moment it was almost too much and I'm not ashamed to say I almost came right there with my cock and balls on her back out in the open air while her titties squished out to the side. She tensed a bit and I thought I'd gotten away with it but looking back of course she knew what I was doing. Why else did she invite me to do this in the first place? She totally wanted to see how far I would go.

But my dumb young self thought she had no idea and it made my dick so hard it hurt. At that point I was too horny to dial it back so I repositioned my hips lower and with my hands still massaging her I started to softly rub my cock between her small but soft ass cheeks. Once this slightly satisfied the ache in my cock I just needed to know what those tits felt like, so I started stroking my hands dangerously close. I could hear her breathing hard and I started to wonder how wet she was. That last thought was too much for me and sent me over the edge. My cock betrayed me by shooting intense blast after blast of cum all over her back while I grit my teeth to hold in my moans. The first shot came so hard it actually got in her hair which only intensified my orgasm. Her back looked like I had emptied the rest of the lotion on it by the time I was done.

At this point I was panting and I noticed she had gone completely still. That nut had stopped my brain from working so I barely had the ability to react when she suddenly turned over on her back to face me. Her eyes were wide and her mouth was gaping open. I couldn't help but think about how I'd love to try and shoot a load in it from that distance lol. Which made me realize my dick was still out, half hard, pointing straight at her with the evidence of my orgasm dripping on her while my proud cock still throbbed.

We stayed like that for a long pause and even though I knew I was in big trouble I relished having my cock out in the open with her staring right at it. I wondered what she thought of it compared to her husband's. I wasn't fully hard again yet but mine is a shower so it was still impressive. I have a thick girth to spread a pussy wide and 7.5 inches when soft, 8.5 when hard. I'm uncut too and that's not normal where I live. The bastard had the audacity to dribble out a little more precum while I thought about this lol. Eventually she lost her shock and did something I never expected. She reached for my cock. I finally let out that moan as she softly gripped it from the underside and stroked it towards her. She used the dripping cum to wet my cock and stroke it to the extreme hardness it had before. Her soft strokes felt so good I eventually started fucking her hand and she brought the other one down to fiddle my nuts.

I think she liked the wild abandon it brought out of me because she started wriggling and the hand on my balls left to spread her bottoms to the side so she could dip her fingers in her pussy. To say I was in heaven is an understatement. I had such a huge smile on my face lol. I wanted to know what she tasted like so I grabbed her wrist and put her fingers in my mouth. There was so much juice on her fingers and the taste was so indescribably good I just let loose. My eyes got wide and I fucked her hand harder. Without giving her any time to realize my plan I reached both hands to finally spread that loose top and frame her breasts just like in my fantasies. They were even better than I imagined. She had no tanlines and her hot pink nipples were so puckered you could only just see her areola.

I'd caught her by surprise but it only made her pant harder and start working my cock with both hands. If I hadn't already cum I'd have blown my load by now looking at those suckable nipples. My hands covered every inch of her breasts as they massaged, pinched, squeezed, and jiggled them. I briefly thought of the lackluster tits on my current and former girlfriends but preferred to focus on the present. I needed those nipples in my mouth so I went bold and pressed my body into hers as I dove in and licked a sweet bud into my mouth. She let out a little cry and I happily learned she particularly loved having her nipples sucked.

She spread her legs beneath me and I used the opportunity to lower my hips and rub my dick between her pussy lips trapped under her bikini bottom. The thought that they were so close to the actual thing drove me wild so I quickly snatched a hand back from her tit, parted her bottoms to the side and slid my dick between her bare folds for a few strokes. My girlfriends had always made me wear a condom so this was my first time feeling pussy without any barrier. Her folds were so slick and I didn't feel any hair so it was incredibly hot and slippery. Her eyes went in the back of her head and she moaned, but when the head of my dick slipped into her canal the tiniest little bit she came back to her senses and pushed me off, scrambling to her cover her breasts back up with her loose top.

We were both panting a while and I waited to see what would happen next when she finally broke the silence. "I shouldn't have done that" she said with the color draining from her face, "I've never cheated on my husband".

"You didn't, I was outside you the whole time" I told her to make her feel less guilty, and hopefully make our other actions feel innocent enough. "You almost weren't" she said with a tremble. If I were ever to get with her again I knew that right now I needed to play my cards right. For the greater good I stuffed my still hard cock back in my trunks and sat next to her on the lounger. "That was an accident, I'd never make you cheat on your husband" I lied.

She looked so confused as she sat up and tried to process everything we'd done. I wanted to make sure she processed it in a way favorable to me so I went in to comfort her some more. "All of that, that wasn't a mistake, and it wasn't wrong" I said in the most heartfelt way I could as I grabbed her hands in mine. She looked up to me with these searching eyes as I continued "you're incredibly beautiful, and it's all my fault for not being able to control it. I've never had the privilege of being close to someone so incredibly gorgeous". She seemed to relax at that as she let out a breath and her shoulders untensed. "We can pretend none of that ever happened" I said with a cheeky wink to get her to smile. She gave a small chuckle and looked down. I waited a few seconds then bobbed my cock a fraction of an inch which drew her eyes back to it.

"You're still hard" she observed. "I'm sorry, I'm trying to think of other things to get it to go away" I lied with a casual chuckle. "It's a little hard in your presence" I added quietly. She hesitated for a moment and I knew she had something to say so I gave her all the time she needed to finally say it. "I know you stole my underwear" she smirked. Not exactly what I was expecting, but not a negative lol. I faked embarrassment and turned my head away to hide a smile. I turned back and tried to give her a puppy eyed apology which she accepted. We sat there quietly for a bit longer and I bobbed my cock every now and then so she wouldn't forget it was still fully hard. She was thinking hard again. Finally, in a small voice she said what I was hoping for.

"You know... if today is going to be a day that never happened I might as well finish you off." I looked at her with gratitude in my face and triumph in my mind.

"You would do that for me? You have no idea how much that means to me."

"Well, it's just, I feel bad leaving you like this."

"To be honest I was also feeling bad about leaving you like that."

She broke out a smile and I saw the heat return to her face.

"What is your wildest fantasy of me? Anything but sex" she hastily tacked on.

I kept up my coy and embarrassed act in my answer. "Well I... I guess I... I don't know, I've always thought you had perfect tits. I can't think of anything hotter than putting myself between them." My heart was racing. If she accepted I could finally live out what I'd been fapping to all the time I'd been in her employ.

She blushed and nodded her head. I thanked the lord and excitement rushed through my whole body as a wide smile cracked my face. I gingerly lowered the loose top from her grip and really took in the magnificence of her breasts this time. I didn't know if I would ever see them again (I would) so I took every second to savor them, dipping my tongue in all the creases, sucking on those nipples with full force, and making sure my hands never forgot their weight or shape.

As I said before, this was a major turn on for her so it wasn't long before she was fired up again. Her hand traveled down and she started rubbing her clit.

"I'd really like to finish you off, if we're saying today never happened" I offered with my mouth still on her nipple. I could still taste her pussy and I wanted to plunge my tongue in her. She surprised me by immediately adjusting to shimmy her bottom off and lay back on the lounger with her legs spread so I could see everything. Just as I suspected from when my cock was rubbing against it, she was completely bare, and her pussy was so wet her juices shined all over it. Her hand continued to rub her clit as I gaped. All I could say was "fuck". I really wanted to feel my cock between those wet lips again so I tried my luck.

"Can I rub myself there like before? I won't go in I promise".

She was so turned on she wordlessly nodded her head and my cock jumped in happiness. I straddled her once more and wasted no time guiding my dick through her wet folds. I made sure to hit her clit on every upstroke and she just kept leaking on my cock. I took the hand I wasn't using to help rub my dick in her folds to plunge two fingers into her cunt. She bucked and I almost slipped inside again but unfortunately my head only caught at the rim of her hole. I wished it had but I told myself I still had a chance to slip it in at some point, I could be patient.

We stayed like this for a while as it felt too good to stop. It wasn't until she started twitching and saying she was about to cum that I leapt off her with my fingers still inside, knelt down and placed my flat tongue on her clit while I pumped her gspot. I tickled her with my tongue until she was writhing with pleasure and finally she erupted. She covered her mouth to quiet her moans, her legs were shaking and juice flowed everywhere as I slowed my hand and lapped it all up. When her body went lax I withdrew my fingers but kept taking slow flat strokes of her clit with my tongue to make her body twitch with a drawn out orgasm. I finished her off by plunging my tongue in her tight pussy and giving her a sloppy kiss on those incredible lips.