Tag: Condom

Categories
Sex

I hooked up with a customer

The day before, I had gotten a phone number from a customer named Lewis. Now keep in mind I work at a big box store, so it’s not like a customer is a huge deal or will ruin any sort of reputation. I described him as a sexy lumberjack with dark black hair and a scruffy, unshaven face in the post from the encounter the day before when we met. I had messaged him during work, but he was busy and we arranged for meeting for dinner. I got off my shift early enough to have plenty of time to prepare. I had considered swinging by Alex’s place on the way home and I almost took the turn to his place but then I stayed course to go home since I had already given one guy a BJ this morning (and 5 the night before) and who knew what would happen later tonight, if I played my cards right things could go well (spoiler – things went well) and 3 guys in a day just seemed like too much.

So I went home and grabbed a snack, did a bit of yoga and prepared. I headed to the restaurant and he was standing outside waiting for me. It was at a local place that’s about the equivalent of maybe slightly nicer than an Applebees, but I didn’t want anything nicer. He was dressed nicely for his typical attire, I would imagine. He was wearing jeans and a flannel tucked in, but he had on an old looking wool coat with leather elbow patches.

We were seated fairly quickly. The dinner crowd wasn’t too busy at 8. We had a great conversation about what we’re looking for in relationships. He’s ready to find new love and I’m not. He seemed disappointed but we kept the conversation going. He has been divorced twice. He blamed being a business owner (construction) on the demise of both of his relationships, but he’s getting ready to retire. I told him he didn’t look nearly old enough to retire. He’s 46, and he told me that he worked so many hours and built his company up so well that it’s like he worked two lifetimes. He didn’t think the business would sell to fully retire, but perhaps he could just get a part time job doing something he liked.

When the bill came, he took it and I told him that I’d like to pay for my own half. He refused and paid. We had each just had a drink through the meal, and I really did think we might be parting ways soon, so I decided to throw it out there that I would like to keep the night going. I asked him if he’d be interested in coming back to my apartment to have another drink, or maybe he’d like to show me his place?

He looked sort of shocked. He laughed and told me he liked the straight forward attitude and said he’d love to come to my place. He signed for the bill, we walked out, and I asked if he wanted to follow me or how we should do this. He told me he’d just leave his truck here. We got into my car and I drove us back. It wasn’t too far. We mostly talked about music. He and I both shared a love of classic rock like Tom Petty.

We got back to my apartment and I asked him if he wanted wine. He chuckled and told me he wasn’t much of a wine drinker, so I grabbed him a beer and poured myself some wine. I turned on some music and we sat and talked for a while on the couch.

I was expecting I’d have to make some sort of a move, when out of the blue he set his beer down and leaned in, kissing me. I kissed back, and leaned backward against his weight as he laid slightly on top of me. As we kissed, he slowly slid his hand up and cupped one of my breasts and started humping my leg slightly. I leaned over and set my glass down and then fully laid on the couch. We laid there for a few minutes, him feeling me up and humping me, before I asked if we should go into the bedroom.

He said yes, and we stood up. I grabbed his hand and walked him in. I stopped him at the side of the bed and pushed him back so he was sitting. Then, I slid my arms out of my dress one by one and let my dress fall to the floor. I was wearing a dark pink matching bra and panty set. I took a step forward and started unbuttoning his shirt and he slowly started caressing my ribs down past my hips.

Once I got the last button, I started pulling his shirt back, but since it was tucked in it was a bit of a struggle. He stood up and pulled it out then dropped it on the floor. He had a great body. He had a lot of dark hair and had well defined peck muscles. We kissed again and I started unbuckling his belt, then the button and zipper. I slid his pants down and he stepped out of them, then he reached in and grabbed my ass with both hands and pulled me close.

We kissed a bit more (he really likes kissing) and unhooked my bra behind my back. I dropped it to the floor, and then he cupped my breasts with both hands and twisted his finger and thumb on my nipples a few times, which made them super hard. I reached down over his underwear, he was wearing tight black briefs, and he was hard. I slipped my hand inside and gave him a grab, then I used my other hand to start sliding them down.

I started stroking him while we kissed some more. I twisted him around a bit and sat him on the edge of the bed, and then I got down on the floor and started kissing the inside of his legs starting with his knees. I looked up at him, he was watching with a smile, and I put my lips around his cock, without looking away. He moaned and then said something like “it’s been a long time since anyone’s done that.”

I asked him if he wanted me to keep going and he said “hell yeah I do!” I smiled and went back to it. I decided to go slow and sensual, keeping eye contact with him until he closed his eyes, then I closed mine. I worked him up and down for a while and he was grunting a lot, which I quickly found to be his way of moaning. I was only a few minutes in when he asked me if I had any condoms. I really just wanted to finish him, I was into it and enjoying it, so I slid out and stroked him slowly and told him I did, but if he wanted I could keep going like this and finish him off.

He told me he would love to give me pleasure too, so he wanted to fuck me. I smiled and leaned over, grabbing a condom from my nightstand and handed it to him. I slipped off my underwear while he slid it on. He crawled the rest of the way onto the bed and laid down on his back with his head on my pillows. He asked if I’d get on top, and I agreed.

It had been absolutely ages since I’d had sex with me on top. I crawled on top and slid onto him easily. I get really wet when I give a blowjob. I almost had forgotten what to do here, but I just started moving my hips forward and back with a little bit of side to side. He had his eyes wide open, staring at my chest while I did this, and I reached down, grabbing his hands and pulling them up. He gave me a few squeezes and started grunting again before letting out a loud grunt. He came quickly. We were only a few minutes in. He made some more grunting noises and his abs were retracting in and out, he was suddenly very out of breath.

He opened his eyes and smiled, telling me that was incredible. He asked if I came and I told him yes, though I didn’t even come close. He got a huge smile on his face.

I slowly crawled off the top of him and reached down, sliding the condom off of him. I carried it into the bathroom, looking over my shoulder as I walked away to see him watching me leave. I dropped it in the trash and came back, he was holding himself. He told me that was a ton of fun and I said it was too.

I went and sat down next to him, then leaned over and grabbed his cock really lightly. I asked him if he had anything left in him for another round and he laughed and told me he hasn’t had that kind of energy in more than a decade. I laughed and let go of him.

He laid there for another minute or two and then stood up and started getting dressed. We went back into the living room and finished our drinks, chatting a little bit about my kids. He tried a few times to poke a bit about a second date, but I assured him I wasn’t interested in anything serious so he dropped it.

He called a taxi. It was sort of funny, because I’d been Ubering and he told me he was too old school for that. The cab arrived 15 minutes later, we hugged, and he left.

I went into my room immediately and grabbed my vibrator. He hadn’t really done much besides turn me on. He was incredibly attractive and I would have enjoyed finishing him off with a BJ more than the sex, but it was a good turn on. I used the vibrator and had an incredible orgasm, then called it a night.

Categories
Handjob Pussy Lick Sex

My First Sleepover

I had been arranging plans to meet Bradley (not Brad!) for a few days now. We met on Bumble. I actually like Bumble a bit more than Tinder, but we won’t get into that now. I was a bit scared that Alex might stalk me or something after last night, but that never happened, I actually didn’t get any texts from him.

I got off work at 5, went home and showered, shaved, and did my hair. We were meeting at a restaurant that both of us wanted to try but had never been. I took an Uber because I really didn’t want to risk driving buzzed again. Over dinner, we had some really nice conversations. Minus the fact that I called him “Brad” at the beginning and he had to sternly correct me to “Bradley,” we seemed to agree on everything. We had each had a glass of wine before our meal arrived, and then had ordered a second one once the meal came out.

He was in a similar situation to me: he had kids, was divorced, but he was actually looking for a relationship. We had briefly discussed this over text, but I really wanted to make it clear that I’m just in it for one day at a time, and that given I’m only a few months out of a 20+ year relationship, that I am pretty well against any kind of follow on.

He had told me early on in our text conversations that I should probably stick to Tinder for these kinds of meetups, but he wanted to see me anyway, so I think things were pretty clear that we were just in this for the night.

After we finished, he invited me back to his place for dessert. I thought that was a little unique, considering most the time I thought people went back for “drinks”. I agreed. We grabbed an Uber to his place, and we got there I asked what was for dessert. “Me,” he joked, and then got out a tub of Ben & Jerry’s Cherry Garcia. Clever, he had asked me what my favorite ice cream was a few days back. Bonus points for sure.

He brought out two spoons and we sat on the couch taking turns shoveling it into our mouths. After some conversation, he sat the mostly eaten tub to the side and crawled up over me and we started kissing. His kisses were more passionate and slow than the previous men I had been with. Bradley was in his mid 30’s, where the others have been a decade younger.

It was at this point that I realized we were absolutely going to be fooling around, and I had just made a post on Reddit the other day about my first hookup cumming in my mouth. The post really scared some reality into me in that I was terrified of catching something from him by giving him a blowjob. I asked him when the last time he had been tested was, under the impression based on my Reddit post that this was a totally normal question, and he chuckled, saying he didn’t really remember, maybe 9 months ago or so.

I shook my head, and he asked if it was okay. I didn’t know what to do because I hadn’t been in this boat before, but he said we could stop if I wasn’t ready. He was being really nice. I smiled and told him everything was great. I took this moment to stand up and slowly unbutton my shirt, staring him in the eyes the whole time. He just sat and watched. I slid down my blouse and then unclamped my bra, letting it fall to the floor.

“I have protection in my room,” he told me, which made me feel good with my nervousness more than likely showing through. I smiled and nodded, and he stood up, grabbed my hand, and then walked me into his room. He opened his drawer, grabbed a condom, and sat it on top, then started taking off his clothes.

He told me he doesn’t do this often, so he’s not really sure what we’re supposed to do, and I told him that I was the same. I unbuttoned my pants and slid everything off, and awkwardly stood there completely naked while he finished getting undressed. He looked up at me and let out a “holy shit” which made me blush and I said “I thought the same thing when I saw you.”

This was a bit of a lie. He didn’t have the absolutely perfect body I’d seen before, but he was still very sexy. He had a hairy chest and stomach, he had a very typical dad-bod and there’s nothing wrong with that. I thought it was kind of funny considering how hairy he was in the fact that he had completely shaven everything around his crotch.

He walked up to me and kissed me again, pressing up against me. His cock was still completely soft, and I reached down and gave it a grab. He slowly pushed his weight against me, knocking me back onto the bed. He immediately got down on his knees and started kissing the inside of my legs, starting with my knees, moving across from knee to knee, then up a little closer, until he arrived up at my pussy (I never know what word to use here. I hate that books use either “folds” or “sex” most of the time. It’s not sex unless you’re having sex!). I think the anticipation felt much better than the actual act of him licking me, but it still felt good.

He went down on me for a little while, mostly focusing slow, long licks between my clit and my hole. He definitely had experience, he knew what to do and it showed. Still, while I was getting licked, I was thinking about what was going to be next. Was he going to fuck me, or was I going to give him a blowjob? I still was nervous about the risks, that Reddit post really freaked me out.

I hadn’t noticed that at some point he must have grabbed the condom, opened it, and put it on while he was going down on me, but he climbed up on me and slowly slid it in. I was mortified. I asked him where the condom was, and he said not to worry, he’s wearing it, and I looked down to see he was telling the truth. I relaxed a bit, and he started thrusting.

It wasn’t but two minutes later that he said he was getting close, and I said I wanted him to cum on my chest. I think the thought of this set him over the edge, because he instantly came in the condom. Watching his face with the grunts almost made me laugh. His face was red and the veins in his neck pronounced. He looked like a guy I have seen doing dead lifts at the gym.

He rolled over onto his back, completely out of breath, and he pulled the condom off and dropped it in the trash, before looking over at me. He told me it was incredible, and I told a little fib and told him I agreed. He stretched his arm out, basically hinting that I should lay on his shoulder, so I took his lead and did so.

He said again how hot it was, and I reached down and grabbed his cock with a very soft grip and started stroking it. I said I agreed, but I didn’t get a chance to do my thing, and he let me play with him by stroking him for a few minutes before he said he couldn’t take it anymore, so I stopped.

It was getting late, and I told him that I had a blast, but I needed to go. He asked me to stay the night. I told him I had to work the next day so I should probably go, and he said he had to be at work around 9, so if I stayed he could drop me wherever I needed. I didn’t need to work until 11, so it wasn’t a terrible idea and I don’t know why, but I agreed. I told him I needed to use the bathroom, and while I was in there I was thinking of excuses to leave, and by the time I came back, he was completely passed out.

I decided that would be a completely asshole thing to do, so I crawled in next to him and fell asleep pretty quickly myself.

I woke up at 6:30, the sun somehow was peering through a crack in the blinds, directly in my eyes. I rolled over and saw that he was completely uncovered, laying out almost like a starfish, completely naked, morning wood in full view. I must have hogged all the blankets. My ex used to always complain about this. 

This gave me a great idea. I slid off the bed and he didn’t budge. I walked around to the foot and as slowly as I could, crept up and slid my mouth over his cock. I slowly started sucking, wondering when he was going to wake up.

It wasn’t even a minute later when he opened his eyes and registered what was happening. I immediately asked him if this was okay, and he enthusiastically agreed. I started sucking a bit faster and with more force, and then the thought of catching something reared in my head, so I leaned back, straddling over the top of his legs, with his cock right near my crotch. 

After I moved, I came back with a bit more motion, and he asked if we could use some lube, since he never does anything dry. I agreed, and he reached up and grabbed a bottle of coconut oil from his side table and handed it to me. I squirted a little in my hands, rubbed them together, and started stroking him again. I started slowly, covering every bit of his shaft. His cock wasn’t quite big enough to stroke with both hands, so I played with his balls a little with my left hand and stroked with my right. 

Soon after, he started moaning very loudly and his cock started pulsing. I could tell he was very close. I grabbed with both hands and started twisting in opposite directions and he almost instantly came. I pointed it up toward his belly button, and his cum started catching in his hair. I kept stroking, slowing my motion, until he was done, and I realized this was my first post-marriage handjob. I had given my ex handjobs here and there, but it was always laying next to him. I hadn’t ever sat there this exposed, and I certainly hadn’t really ever watched everything unfold like this. It was incredibly hot, and it made me want to do it again, and soon. 

He looked down at his stomach and laughed at the mess. I laughed with him. He said he needed to rinse off before we head out, but that I should make us both some coffee if I drank it. I threw on one of his shirts and went out there to figure it out. I made the coffee no problem, and he came walking out wearing his pants but no shirt. He made a joke about how his stomach was clean now and it made me blush a little.

I told him the coffee was about done brewing and I walked over to the living room and grabbed my shirt from the floor. He was watching me and said something about how he wishes I hadn’t been so careful bending over. It took me a second to register that I even had been careful not to just moon him and I chuckled a bit.

We drank our coffee and then I went and got dressed. He told me he had to brush his teeth, and I think it was one last excuse to watch me change, because he didn’t really pay much attention to his teeth.

He asked me where he should drop me off, and I told him where I lived. He kind of looked disappointed and I gave him a questioning look, and he said it was the complete opposite direction of his office. I told him it was fine, I could take an Uber, and he told me it was fine, he could be a little late.

I insisted and called the Uber, he felt bad and tried to hand me some money to cover it. I declined. The Uber arrived and took me home, and I took my own shower and got ready for work.

Categories
Blowjob Sex

My first date, which was my first hookup.

This was written February 7th, but I set the date to December 2, so that I can keep a proper timeline.

It was December 1st, 2002. I was talking to an old friend of mine, Steph. She and I were talking about my divorce (of course) and that I should get out there and meet new guys. “You’re only 40, you need to get out there.” I disagreed. I was in a relationship since I was a Junior in High School. I needed some “me” time.

She insisted. But, she didn’t know how to help me. She didn’t know anyone, she had been married for 10 years herself, but her coworker Kelly was younger and was always talking about dates, so she called her so that we could have lunch.

We met for lunch the next day, Steph introduced Kelly and I, and we hit it off well. I’m a lot older than her, so it was a bit awkward for me, but she didn’t seem to notice at all. She’s in her mid twenties, maybe 24-25, and she’s loving the single life.

This is where Steph decided to chime in and ask if Kelly knew of any guys that could go out with me. It was super weird watching these two women talk about me hooking up, but Kelly was incredibly helpful. Awkward for me again, but for her, just another day. Kelly insisted that I go out with her friend Nate, she said he’s a super good looking, muscular guy who people say is a great lay.

I brushed her off, said I’m not really interested, but Steph said that was exactly what I needed, and Kelly agreed. Basically they said that I just need someone who will fuck my brains out to get me into “the game” and get me completely engrossed into the single life. I absolutely insisted that I was not committing to hooking up with someone, but that it could be fun to go out. They both harassed me about that, but I stayed strong.

Kelly texted Nate, and showed me the texts afterward. Basically, she said she had a super hot MILF friend that he needs to go out with ASAP. It was only 3-4 texts and then she asked me for my number to give him. I gave it to her, he texted me “Hi, Kelly says we should meet tonight, are you free?”

Steph grabbed my phone, insisting that I didn’t get to be a part of it. She laughed a bunch and I kept reaching for it, trying not to make a scene over the table, but eventually handed it back. Steph suggest we meet at fucking Applebees.

“Applebees?!” She laughed, and said it was the first place she could think of.

We thank Kelly, and we head back to my apartment so I can get ready. Since it was a Saturday, the kids were with their father. This was only the 2nd weekend of our arrangement so I was a little hesitant in case they needed me, but Steph insisted it would be fine – I have a phone and could leave at any time if needed.

I have no idea what to wear. So, we played dress-up with my clothes for a while. We landed on this and Steph took a picture to send to Nate, but I absolutely wouldn’t let her. As I was changing, she sent it anyway, saying “so you know who you’re looking for.”

He replied with a thumbs up. Hmm. Curious response.

After we decided on the outfit, she was ready to go home, but I was an absolute nervous wreck. I still had 2 hours until we were meeting and I insisted she stay to distract me. We drank wine and watched tv until it was time to go. I drank a few more than she did. She dropped me off at Applebees, and I was even more of a nervous wreck.

He arrived just a minute or two later and immediately recognized me, I mean I was wearing the exact same clothes and everything, I had taken my jacket off to make sure of that. We talked to the hostess and then grabbed a high top table in the bar area. We ordered appetizers to share and some drinks.

Nate absolutely lived up to the hype from Kelly. He was tall, in very good shape, and handsome. He looked like a frat boy to me, but he was telling me how he had graduated a few years ago, so at least he wasn’t still a frat boy. It was after a few drinks that we started getting into the real conversation rather than just talking about the weather and local stuff.

He seemed genuinely curious about my relationship and how I lost it. He said that although he is loving the single life that he wants to settle down and get married and have kids. I joked that I’m absolutely not that for him, and he said something along the lines of “well that’s also ok by me for today.”

After our fourth drink, he asked if I wanted to go back to his place to get another drink that is much cheaper. I agreed, and we took an Uber. It was on the way that I really started getting nervous and he saw it. He didn’t need me to say anything, he just said “hey look, there are no expectations except that we have a drink, ok?” I just half smiled and nodded, and we were there in no time.

We walked in to his one bedroom apartment and it was better kept than I thought it would be. Still sort of a mess, but tidy enough to not be embarrassing. He made us a drink and we sat on the couch. He put some music on, I kind of chuckled because it seemed incredibly cliche.

In the middle of our second drink at his place, he leaned over and kissed me. He stuck his tongue into my mouth and I was in shock. I hadn’t had a deep kiss like this in over a decade. Not knowing what to do, I just sort of swirled my tongue back on his. He reached up and grabbed my boob, and I kind of laid back on the couch. He started squeezing it a bit harder and then he started grinding his erection on me.

I stopped him and told him I had no idea what I was doing, that I don’t know what to do and he said he would take the lead if I wanted, or we could stop. I told him that as long as he’s okay taking the lead and showing me the ropes that we could keep going, but if I said we need to stop that we would stop. He completely understood.

So we’re making out on the couch, he’s grinding his erection on me and playing with my boobs, and he slid his hand under my sweater and bra. He asked if he could take it off, and I nodded. He unclasped my bra with one hand and then we worked together to take my top off. As soon as my boobs were free, he cupped them both and then sucked on one of them.

He laid me back down, and then took his own shirt off, showing off his absolutely perfect body. I think this was finally when my nerves started subsiding and I started just really getting into it. He then slid his hand over my crotch, still over my pants, and rubbed a bit. We were both breathing hot and heavy. He asked if I wanted to feel his cock, and I nodded. He rolled over to the side so I could reach it, and I gave it a few strokes over his pants.

I noticed it was incredibly hard, I remember that being the first sensation of touching another man’s cock. My husband hadn’t been that hard, maybe ever.

After a few more strokes, he unbuttoned my pants, sliding them down while I lifted my hips so he could slide them off. I’m now just in my panties, he’s still wearing his jeans. He rubbed my crotch a little bit over my panties before asking if he could take them off. I said yes, and he slid them off.

He started rubbing me, then slid a finger inside, rubbing against my clit a few times before inserting his fingers up inside me. He did this a few times, and then he asked me if I would want to go into his room, that’s where he keeps his condoms.

I told him I did, and he stood up. I stood up, and he grabbed me, pulling me in close while holding my ass, and kissed me. He said “I’ll be gentle if you want, but I can be as rough as you need.” I smiled, and then he led me into his room and said to lay down.

He watched me crawl onto the bed, told me I’m incredibly sexy, and then opened his drawer and pulled out a condom. I was on my back, watching him as he unbuttoned his pants and pulled down both his pants and his underwear in one motion, and I watched his cock spring as it was free.

I didn’t see it for more than a second or two before he was rolling the condom onto it. He looked at me, caught me looking, and asked if I liked what I saw. I said I very much liked it, and he asked if this was all okay. I told him I wanted him to fuck me, and I told him that he didn’t need to go slow.

He smiled a huge grin and climbed on top of me. Immediately he thrust inside me and started pumping. We were in missionary position, and he was grabbing my ass with one hand while supporting his weight with the other. After just a few minutes, he said he was getting close, and I said something like “Yeah baby, cum,” and he pulled out of me, ripped off the condom, and started coming up.

Without thinking, I leaned in, taking his cock into my mouth, and just sucked. He came pretty much instantaneously, and that’s of course when the reality sunk in that I’d never done this before. I had never had cum in my mouth. I had always thought the sound of it was gross, my husband had only asked about it maybe twice in our entire relationship, so it just never had come up.

Well, lucky for me, I loved it. He was moaning, I could literally feel his orgasm happening, and it flipped a switch for me. I had never felt this “responsible” for the pleasure of another person before. But, not knowing what the hell I was doing, I just kept sucking.

He kept wriggling and writhing but it all seemed pleasurable, until finally he pulled back and said he couldn’t take it any more. I asked if it was good because that legitimately concerned me, and he said it was one of the best feelings he had ever had in his life. I took that as a compliment, because I know he had been with multiple people.

We laid there naked for a little bit, talking about something I can’t really remember, and then I said I should probably be heading out. He said he was getting tired so that was probably the best anyway.

As I was getting dressed, I hit the Uber button, and we exchanged our pleasantries, he said he’d be willing to show me more anytime. I left, went home, and couldn’t fall asleep. I was sitting there reflecting, and even though we had sex, my favorite part of the night was the very end, when I was sucking on him.

That’s when I realized that I missed out on a lifetime of something I now love, and that there’s no more holding back. I don’t have as much life left to live, and I can’t wait around.

I’m now just going to be me, whatever that means.

A month later

About a month later, I made my first Reddit post about this. Basically, I didn’t have sex again with someone but wanted to know if this was normal and something to expect. I gave three more blowjobs (which I’ll tell about later) but not sex until after the post.

For some clarity, after the Reddit post, I texted him and asked him a few things. First I asked about STI testing, which he told me he had just gotten tested the week prior and was completely clean. Second, I asked him why he assumed I would swallow, and he said he didn’t. He was intending on cumming on my chest, but then I took it the rest of the way. He and I haven’t communicated again since.