A First Time for Almost Everything

I recently did something that I thought I would never do... I gave a handjob to another man and let him cum on me.

For years, my husband has tried to get me to tell him about sex I had before we met. I think it's a little weird that he wants to know the gritty details about the guys I was with before we met but he gets really turned on just asking about it. I have told him about the first dick I saw and how big he was (luxurious would be an understatement) and a quick story about giving a guy a handjob in his car before it turned into the inevitable BJ. This drives him crazy and we had really awesome sex afterwards, but it's still a little uncomfortable. He says he's turned on by thinking about watching me with another man but I have no desire to fulfill his fantasy, well, until recently.

I work a regular, mundane day job five days a week and a couple of nights a week I wait tables at a bar to help pay for all the extras it takes to raise teenage kids. I get the usual flirts that happen when I smile or wink when taking their drink orders and the occasional really young guy that gets a little too excited and tries to give me his number when he slides his credit slip to me when he pays.

I let it all slide. It's flattering, I guess, but I'm not interested in anyone other than my husband except for the occasional girl/girl fantasy that I have and I thank PornHub for being there for me when I get weak and have to satisfy my curiosity when I get the rare alone time required.

This changed a bit recently when we scheduled a family vacation that my honey is really not enthusiastic about going on, and joked that he'd go and be cordial if I'd promise to give a stranger a hand job while we're there. I agreed just to shut him up but the thought of it actually turned me on and I was shocked at finding myself having that fantasy a couple of times, when I would usually be enjoying a more sapphic visualization in my head while masturbating, when he's laying next to me snoring and dreaming of whatever he does.

Last night at the bar job, I had a moment when I realized I was actually more open to the idea of jerking another man off while I was talking to a regular that has always been really nice and polite but a little flirtatious in the most subtle ways. He works part time at the bar and he's a really decent guy. He walks by and hip bumps all the servers and female bartenders and I have taken to lifting a foot behind me to play like I'm trying to trip him when he walks behind me. I felt all weird about this and even told my hubby about it and he said it doesn't really bother him but some guys may take that as me showing interest where I have none, so be careful.

One of my husbands "weird" fantasies is seeing me with a black man. I know this is pretty popular with some guys, as evidenced by it being one of the most popular categories on PornHub and one he spends time perusing fairly often. I've never been attracted to black men myself, although I went on a couple of dates with black guys as a young twenty something. And yes, he knows and has regularly asked me to tell him stories about anything that happened. Truthfully, I did have sex with each of them after a couple of dates and while both were well endowed, their focus was only on their own pleasure and neither occasion was actually anything really special at all. They were very much the same... too fast, too deep and even though it lasted a long time, I just couldn't get into it. I chalk it up to them being young and inexperienced or just plain unconcerned with their partner's enjoyment.

I guess I should mention that I'm mixed. Maybe that's why I was never really attracted to black men. It's a little creepy when your dad is black and the guys that I went out with had some of the same mannerisms and physical traits. It was just never my thing. But back to my present predicament...

The guy at the bar, let's call him Steve, is a little older than me, mid forties, and is light skinned. He is well mannered and takes care of himself. He comes in on days he's not working and always has a little entourage of twenty-ish white girls hanging on to him. I told my husband about this and he's had a ball with all the innuendo he can come up with. He's even met him and kept teasing me quietly and even asked if I'd noticed he was checking me out while we ate lunch there one afternoon.

Like always, Steve came to work on Friday night and was congenial and busy as ever. While I was behind the bar filling a pitcher of beer and chatting with one of the other servers, he slipped in between us and gave us each a tiny hip bump and said "Good evening ladies!" and as usual, when he started to walk away I raised my foot behind me to play like I was tripping him and he actually slipped and almost went down. I spun around to try and help steady him and my hand went naturally to his waistline and his to mine. When he touched me I had my had on his firm stomach, I had a flash in my mind that he felt really toned, he smelled really nice and he had his hand on my hip and it felt good. I haven't been touched by another man since I met, and got married to my husband. That's been almost twenty years.

I immediately felt a wave of guilt and pulled away from him and apologized for having tripped him up and having put a hand on him. He said it was ok, he shouldn't be bumping into anybody on a wet bar floor, especially a married woman. He winked and went about his business. Throughout the night I'd see him carrying ice tubs to the bar or stocking the reach in beer fridge and couldn't get the thought out of my head about how firm his stomach was and even, for the first time, noticing his jeans and how tight they were to his butt. I found myself sneaking looks at him and once I even watched him carrying a huge bus tub full of ice and beer and noticed how tight his jeans were in front too.

All the things that my husband says about he knows "size matters" and that he'd like to see me with a man that has a bigger dick than him and see me get off on one flashed through my head. He's always saying something about how small he is (he's not!) and how if he was ever unable to satisfy me that he'd be ok with me still having sex to be healthy and happy. I didn't like that kind of talk but over the years I realize that he means it because he just wants me to be happy and he is getting older and worries about how well he performs. He's bought me more than a few toys to make sure I enjoy myself and I feel bad sometimes even though he says it turns him in to hear me masturbate while I think he's asleep. I told him once that "sometimes I just need a little more 'old man' and I don't want you to hurt yourself!" He took this with a giggle and bought me a dildo that's very realistic and has lots of potential. I'll have to give it a try sometime.

Around ten o'clock Steve finished his shift and as usual, grabbed a beer and a stool at the bar and watched the band and chatted with other servers and regulars. As business started to dwindle, I finished up my side work and started looking for ways to get cut early so I could go home and vent my newfound frustration with my honey! I've never really paid attention to other men, even a little, while I'm out and about and I've never gotten horny and flown home and fucked my husband with that in my mind. I've always said that "feels wrong."

I'd filled a bus tub with wrapped flatware that was pretty heavy and as I was moving it from a table to the servers station, I was slipping around on the ever wet floor in the bar area. I just managed to keep from dropping the whole thing when Steve swept up beside me and grabbed it from me. When he reached over the top to grab it, the back of his hand brushed the side of my boob and I felt an almost electric shock course through me. It was totally innocent but my mind raced through the moment and I felt my nipples stand up, hard and I know my face flushed red.

He definitely noticed because when I made eye contact while thanking him for helping, he was staring at my erect nipples and looked up with a smile. "Sorry if I startled you when I grabbed that, the bus tub I mean." I told him thank you and went to do my exit paperwork so I could go home. It has been so long since I caught another man ogling me that I was flustered a bit and a little turned on a little too. I don't think it happens that often despite my husbands raving about how hot I am and how other men want me, all the time.

I decided to finish up and for the first time take my "free after shift drink" and sit with another girl who was also done, and chat for a minute before heading home. After all a small drink would take the edge off the evening and I'd be relaxed and ready to jump my husbands bones as soon as I got there!

I ordered a seltzer I'd been serving a lot of to ladies, and plopped beside my fellow server at the bar. We talked about work, how the regular customers get way too drunk and how other servers don't do their jobs... the regular, catty, bar worker talk. The band finished what would be their next to last set and I had just finished my drink and decided it was about time to text the "old man" and let him know I was driving home and hit the road. My coworker said "Hey, come smoke with me (even though I don't smoke) on the patio before you leave." I stood up and realized I don't have the tolerance I used to and I felt a bit tipsy from the seltzer. We headed towards the patio while I fumbled for my phone and keys, and Steve walked up behind us and said "Shall I walk you ladies to your cars? You two look just a little tipsy." We hold him thanks, but we're just going to get some air together on the patio before we have to drive, and went out the door.

When I reached for the door, it swung out away from me unexpectedly and it made me stumble just a bit. Steve had swung open the door for us and followed us out into the night air. He asked to make sure that we were ok to drive and sat down with us at a table while my friend lit up a smoke. I couldn't help but look at him as he sat down and the bulge in his pants was very evident as he did. We both thanked him for looking out for us and sat back and began to chat. Her phone rang and I felt kind of awkward when she answered it because I didn't know what to say and I was sitting here with an attractive man that had made my nipples hard just a little bit ago, and they started to firm up again as I realized it.

She was full on in a conversation with her boyfriend when Steve said "I hope it's just the cool air and not the alcohol and my presence causing that." and I made eye contact with him and blushed. Maybe it was the alcohol or maybe all the fantasy talk with my husband but I shocked myself when I said, "It's a little bit of both. It's cool out here and I noticed you looking at them earlier!" His eyes went wide and his mouth dropped open. I pushed my arms together to make my boobs push up and outward a little in my tshirt and asked him if he liked what he saw? He stuttered a "Yes, b-but I think your man would kill me for saying so!"

In a microsecond, I saw myself on vacation, sitting in front of Steve with his dick in my hands as my husband watched from nearby, encouraging me. Although I was shaking a little and my words twisted a little on the way out, I said " You'd might be surprised what he's into." and looked down at his crotch. When I did, I swear I saw him grow a little bit in his pants, enough that he had to adjust himself. I asked him " is that because of the cool air or my presence?"

Laughing a little, he pushed his hips forward and turned towards me more in his chair. I could see his penis growing down his thigh under his pants and I gasped a little. All kinds of thoughts went through my brain. Should I keep looking? Was this cheating?! What would he do if I asked to see it? What the hell am I thinking?! I took a breath to say something, anything to change the subject when our coworker, still in the phone leaned over and said, "I've gotta go! Are you ok to drive?" I stammers a yes, and she all but dashed away to her car.

I looked back at Steve and he had his hand on his bulge and squeezed it a little. When I looked up at his eyes he was staring at me with a sly grin on his lips. I immediately stood up and nearly knocked the table over which caused him to hop up and steady me by one of my shoulders. All the same images flew through my mind and the guilt I felt about the situation. I shocked myself with what I did next. He was standing directly behind me and I pushed my ass back into him, feeling his hardness against me and said in a nervous but seductive voice " Will you show it to me?" I don't know exactly what happened but I felt like I'd stepped over a line that I should regret, all the while hearing my husband whisper "That's it, stroke his cock and rub his balls. Oh yeah! That's so fucking hot baby!"

I walked away from him, out around the building to my truck that was parked in the far end of the lot, under a big tree, in the dark. I walked fast, not looking over my shoulder, hoping he wasn't behind me. I heard the band kick into their last set as I fumbled with my key remote and unlocked the doors just as I got to the side of my truck and dropped my keys. As I bent to grab them, I saw him in the corner of my eye. He was a few feet behind me and had a boyish and worried look in his face. He sucked air between his teeth as I bent over to pick up my keys and asked if I was serious or was I fucking around with him. I turned and faced him and barely audible, I said... "Really. Can I see it?"

He came closer and held his hands up to his shoulders and said "If you want to see it, you have to take it out. I'm not going to expose myself to a married woman in a parking lot." I almost laughed and realized the situation I'd put us both in. He moved closer, less than a foot from me, and I reached down and rubbed the huge erection that was pressed against his pants. "Holy shit! It's huge!!" I gasped and squeezed the shaft of his dick and grabbed the button of his jeans and tugged. I fumbled his zipper open and his dick pressed up and out of the waistband of his underwear. I could see the head in what little light there was from the nearby buildings and ran the palm of my hand over it and then down towards his balls. His jeans dropped to the ground and he leaned forward like he was going to kiss me when I pulled back and said "No. I don't want that. I just want to see your cock."

I was a bit of a late bloomer and my first boyfriend that I was with was a white guy a couple of years older than me. After a bit of awkward conversation and rubbing on each other, I took him out of his pants in the front seat of his car in front of my parents house and stroked him off. He was about eight inches long and thick enough that I could just barely touch my fingertip to my thumb. I played with his dick until he came all over my blouse. I had no idea what to to do at the time and I was so nervous that I hopped out of the car and snuck inside so my parents would see what I'd been up to. He was also the first guy I had sex with and I remember being scared that it would hurt after talking about his size with a friend and it did... until it didn't.

Steve thumbed the waistband of his shorts down and his dick sprang out into the night air. I looked down and grabbed it, wrapping my hand around his shaft and couldn't get my hand all the way around it. He was so thick and longer than any guy I'd ever been with. I was so nervous, yet intrigued and wanted to see him closer, so I knelt down and took him in my hands and moved a little closer. "It's so big!" I stuttered. His cock was huge. Like I said, it was thick enough that I couldn't touch my fingers around it, almost bigger around than my wrist, and nearly as long as my forearm. If I had to guess, it was every bit of 11 inches long. I'd only seen one like this on Pornhub and cringed at the thought!

He asked "So now that you've seen it, what do you want me to do? Should I put it away and go home all worked up?" Shakily, I said "That wouldn't be fair would it? I get to go home and fuck my "old man" while you have to drive home with that stabbing at your pants, huh?" With that, I stood up and opened the back door to my truck and told him to get in. He wasted no time. As he moved over behind the drivers seat, I hit the latch that folds up the other chair and climbed in on my knees and pulled the door closed behind me.

I pulled his jeans and shorts off one leg and l moved towards him. He spread his legs out wide and I could see his dick sticking straight up towards my face, pulsating with his heartbeat. I had zero intention of fucking him, but I did want to make him cum. I remembered my first, all those years ago, and pulled my tshirt over my head and leaned closer to his dancing prick. I took him in both hands and stared at him for a moment. I could smell his cologne and hear him breathing but couldn't see his face clearly in the dark of the tinted back seat. I began stroking him with both hands, loving the feel of his rigid cock.

I rubbed my hands up and down his firm abs and down his thighs before returning my grip to his dick. He said "Can I see those titties?" And I didn't think twice before I leaned forward, pressing his cock against my chest and said "You have to take them out. I don't want to be accused of flashing a coworker!" He fumbled with my bra strap for a second and I felt the clasp release and I leaned back and let my girls go free. I have big boobs, like really big boobs and I'm self conscious about them as I get older after kids. He made me feel pretty good when he reached out and cupped one in each hand and said "My lord girl! You have some beautiful titties!"

I grabbed my boobs and pushed them up together and leaned forwards as I rubbed them all over him. He grabbed the base of his dick and pushed the shaft into my cleavage and I closed them around him. I tried to stroke his cock with them but it felt awkward and everything was so dry. I let them go and took him in my hands again and began pumping him up and down, feeling his heat and his heartbeat pounding in his cock. I tried to spit on one hand but couldn't. I could feel the alcohol in me and my mouth was so dry. I squeezed his shaft from the bottom up to the top and a huge drop of precum oozed out and down the shaft of his dick making it slippery and wet.

I grabbed my girls and wrapped them around him again and used my legs to bounce up and down and rub his dick. This made him moan a little and he began pushing his hips up to meet me. I pushed my chin down to my chest and looked down to watch him pop in and out of my boobs, when he lifted his butt up and pushed up between my tits and the head of his cock touched my lips, and then again. I was so wet and so excited that I opened my mouth and let the head touch my tongue, then I wrapped my lips around it.

I let go of my boobs and grabbed his cock and stroked the shaft as I circled his head with my tongue. Teasing the underside just under the tip and licking up and down the bottom of his cock. He placed his hands on the sides of my shoulders and closed his eyes, lifting up his hips to match the rhythm of my mouth bobbing on him. I opened my mouth wider, spit and his juice running down over my hand and his shaft, and took him in as far as I could.

I'd forgotten about being married. I didn't feel any guilt. I just felt horny as fuck! I could feel my pussy aching and the wetness soaking my panties and jeans. I pulled on his leg and threw mine over it and pressed my swollen clitoris against his shin and rubbed it against him, matching the rhythm of my head and his upward thrusts. As I did this, I started to cum. I shuddered and bucked against his leg, as waves of orgasm shook me. I felt the wetness saturating my thighs as I came harder than I had in years. He pushed me backwards a bit and grabbed his dick and moaned loudly as he stroked his cock. He started cumming, a lot of it. He shook as his cum squirted out onto my tits, my chest, my neck. I was still in the throes of my own orgasm while he continued to pump a huge amount of cum onto me. He let go of his dick and I grabbed it and squeezed it as I continued to stroke him, making him shudder and spasm.