Month: December 2022

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Blowjob

New Year’s Eve. my coworker

When I woke up on New Year’s Eve, I assumed I’d be spending the evening completely alone. I had been talking to some guys on Tinder, and most of them already had plans. A few invited me to come out, but being with a stranger from Tinder and his friends just didn’t sound appealing to me. Honestly, a glass of wine and a book sounded like good enough distraction from knowing I wasn’t going to be with my kids on the first day of the new year for the first time in their lives.

I went to work as usual, and we were all getting excited because the store was closing early because of the holiday. Someone was going around inviting a few people to dinner, which I graciously accepted.

We closed the store, finished everything up, and were out the door before 7. We all decided to meet at the restaurant, and I drove straight there. All in, there were just four of us. It was a nice time and a good distraction. As we finished our dinner and split the bill up, I was intending on going home, but then one of the girls asked me to join her with some more of the crew at the bar that was just around the corner. I was hesitant, but she insisted since I didn’t have anything going on.

It was close enough that we both just walked together. Once we got there, there were a lot more coworkers, and we had a good time. There was some dancing, but mostly drinking, and it was pretty easy to have conversations. It didn’t take too long before almost everyone I knew was gone. I think everyone just did the ol’ Irish Goodbye and disappeared. At this point, there were only 6 of us left, and we took a seat at a table and ordered one final round before we were going to part.

Three of them downed their drinks quickly and took off, and then it was down to just the three of us: Jade, who was the one I came with from dinner, and Alex, a slender, younger guy in his very early 20’s that I didn’t know too well. I still had a good 2/3 of my drink left when Jade got a text and told us she had to leave. She said I could join her, but it felt more like a pity invite than anything else, so I told her that I was completely fine and she should go have fun.

We’re down to just Alex and I. For some more context, we had talked about how he’s working full time at the store while attending community college part time. He’s a bit of a loner, he’s really close with his family, and he also didn’t have plans for the evening. He doesn’t have many friends, he’s not really into the whole party scene that a lot of his classmates are into. He just wants to get through school so he can get into grad school and become a pharmacist.

He asked me if I wanted to keep hanging out. I declined. We both finished our drinks and walked out together. He asked where I was parked, and I told him it was a few blocks away at the restaurant, and he told me he’d be happy to walk with me to make sure I was safe. I kind of laughed in my head, because this gentle guy wouldn’t protect me against a fourth grader, but it was a great gesture and I accepted after a bit of a fight about it.

Once we got to my car, I realized now I should drive him back to the bar, so I asked him if he had parked there as well. He laughed, told me that he had taken the bus here so he was just going to walk back. I asked where he lived and it was pretty far, and I volunteered to drive him home. Just like me, he fought it a bit but then caved.

We sat there in relative silence for a bit, and then when we started getting close and he was giving the turn by turn directions, he said that he had a bottle of champagne that was a few years old and he had some white wine, and if I wasn’t doing anything we could just watch all the Times Square stuff together. It seemed quite harmless, and this guy had not one single ounce of flirt in his body. It almost felt like a girlfriend asking me to come over. I agreed.

We went upstairs to his apartment and he quickly ran around picking up the few things that were out of place. He asked if I wanted the champagne or the wine and I laughed and said we should save the champagne for the new year’s toast, so let’s get the wine.

He grabbed the bottle from the back of his cupboard. It was pretty obvious that it had been there for a while and he was saving it for a “special occasion.” He didn’t have wine glasses, so he grabbed us each a pint glass and filled them up. I laughed and asked if he was trying to get me drunk, and he blushed a bit then told me he could pour some back. I told him it was fine and that I can just sip.

We turned on the TV and watched some of the New Years Rockin’ Eve. We basically both just made fun of the people because neither of us really keeps up with this kind of thing. We drank, we sat in silence, and occasionally we dove down a rabbit hole of conversation. One of them ended up finally switching to sex as the topic.

On this topic, I learned that he’s had sex with one girl, and he’d gotten a blowjob from a different girl, but these were both over 3 years ago. Since then, he’s been single and he never has enough confidence to talk to women. We had already discussed that I’m newly single, we had talked about my relationship, how I was married to the same man and had been with him since high school, and that I’m finally enjoying my newfound freedom, just now getting to explore my own sexuality with others.

One of those “freedoms” is being able to do whatever I want, when I want, as long as it’s a weekend or the kids are at school, I don’t really have the responsibilities I used to have. It was at this time that I looked up at the TV and saw that there was a little over 12 minutes left before the ball dropped in Times Square.

He had been fairly uncomfortable all night. I continuously caught him sneaking glimpses at my body, but he was a complete gentleman. I could tell he wanted to say something but feared rejection. I just knew it, deep down. I didn’t know how to suggest anything with him. Prior to now, the topic of either sex or a blowjob came fairly naturally from the guy, and I fed off that. So I just decided I had to take the lead.

So I asked if I could make a suggestion, for the ball drop and the rest of Rockin Eve. Of course, he agreed, having no idea what the suggestion was.

I told him that I thought it would be fun to see if I could get him to cum right at midnight as the ball dropped. That’s all I said for now, and I just looked at him.

He said “uh” and “um” and “uh yeah” like 50 times each, I swear I could actually see the gears turning in his head trying to formulate a sentence. He awkwardly shifted on the couch while muttering, and I told him I’m going to take that as a yes.

He shook his head and said yes.

I sat my wine cup on the side table and crawled in front of him. I told him I had a rule, that this is a one time thing, and neither of us could speak of this again. After tonight, this never happened. He shook his head and said yes, that worked for him.

I slid his pants down, and his underwear as well. He was already as hard as a rock. I palmed it and gave it a few strokes, looked up at him and reconfirmed: we will never talk about this again, and you won’t tell anyone. He agreed.

I started slowly. I pulled his cock to the side and started kissing it, and he started breathing incredibly quickly. I told him to relax, and he said ok and leaned back. I told him that was more like it, and then I gave one very deep suck, all the way down. I hadn’t had a guy moan like that on the first few seconds before, and somehow his cock felt like it got just a little harder.

I started sucking, moving up and down slowly, and he felt like he was about to cum. Knowing that it wasn’t yet time, I slowed down a bit, switched to my hand, and looked at the TV. There was only about 2 minutes left, and I asked him if he could last another two minutes. He shook his head without saying anything, just breathing hard.

I told him if he can’t last that it’s fine, and then I went back to work. After no time at all, I heard them starting the countdown and I took a quick break and told him I wanted him to cum at zero, to which he nodded and looked visibly shaken. When zero happened, the music started playing, and he didn’t cum, so I started sucking harder and faster. His moans started getting louder and his breath sounded like he was running a marathon.

After maybe a minute, possibly a little less, he exploded. He grabbed the pillow and shoved it into his face while he started moaning these quick little moans, it almost reminded me of a puppy yelping. I continued to suck until his cock stopped throbbing, and then I slowly slid it out, kissing it a few times as it lost a little bit of its hardness. I reached up and pushed the pillow to the side, giving him a smile and asking how it was.

Still not forming a complete sentence, he basically mustered out that it was the best thing that’s ever happened to him. He told me he felt like he won the lottery. I smiled and shook it off, I told him I was so glad and that I had a lot of fun.

He actually apologized for not cumming right at midnight, and I laughed pretty hard. I was actually finishing off the last gulp of my wine and nearly spit it out. I reassured him that it was completely fine, I didn’t actually expect it to happen, I just thought it was a fun little game. He seemed relieved.

I had the early shift the next day. Luckily, we opened a few hours later than normal because it was New Year’s Day, but I still had to be there at 9. I told him I needed to get going. He awkwardly said something like “Can I, uh, can I do something for you too?” while he was getting his pants back on.

I smiled and told him that I’m sure I enjoyed it every bit as much as he did, and that he needed to remember the rule. This never happened. He told me absolutely, and he did the dorky motion like he locked his lips and threw away some invisible key.

I winked and turned to leave. He said “wait!” in a loud voice, and I turned around. He wrapped me up in a hug and said thank you. I smiled, and said “no, thank you,” and pushed my finger into his chest and walked out. I got out to the parking lot and looked up, I saw that he was watching me through the window, and as soon as I did, he quickly backed away. I laughed and got into my car.

Looking back on it, I absolutely shouldn’t have driven, but I didn’t feel very buzzed at all. It took me about 10 minutes to get home, luckily his place is almost exactly halfway home from work, so I knew right where I was. When I got home, I immediately crashed.

The next morning, January 1, my alarm went off at 7. I had a text from one of my kids and a text from Alex. I replied first to my daughter, wishing her a happy new year and telling her I couldn’t wait to see her tomorrow, and then I read the text from Alex. He told me it was amazing, the best he’s ever felt, and he would love for a round two, or would love to return the favor.

I reminded him of the agreement, that we’d never speak again, and he said yeah, he remembered, but just wanted to throw it out there. I said let’s just stick to it, and he said okay.

I got ready and went in to work. I was glad he had the day off, because I didn’t want to risk anything.

During my lunch break, I saw I had another text from him, where he basically said the same thing again. He said he was super horny and that he wanted to meet me that night. I was pretty firm in my response, I said that he’s not living up to his end of the deal that we never speak about it again, and I told him I already had plans that night.

He asked what I was doing, and I ignored him. This is actually when I made a Reddit post. I didn’t reply that day, and he didn’t text me again.

Afterwards

A few days went by, and we hadn’t spoke. We were friendly, just sort of saying hello in passing at work, nodding, and smiling. In passing one time, I stopped him and asked him how he was doing, and he said he was great. He apologized for breaking the rule, and I said I understood, but it can’t be broken again. He said he completely understood and respected it, and it’s now just a really good dream he had. I thanked him and got back to work.

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Ass Lick Blowjob Pussy Lick

Christmas Eve. Drunk, Horny, Lonely.

My ex husband and I haven’t fully worked out the kinks in our schedule with the kids. What I mean by that is that I get the kids during the week, and he gets them during the weekends. We both agreed to that and we agreed on every other Christmas/holiday as being an exception. To start things out since we just got divorced, this year was his with the kids.

Since we’re still very amicable with our relationship, my ex did say that I can visit with the kids a bit on Christmas, and I came over in the morning to make sure I did that, but on Christmas eve, I was all alone all day. I was hoping to work, but I got my shift cancelled before coming in. So I was stuck with nothing. I went to the gym. I typically go to the gym in the mornings, but this time, since it was Christmas eve, the gym wasn’t open long.

I started the morning doing yoga and listening to an audio book. That got a bit boring, so I went to the gym. While I was there, it was nearly empty, and a guy approached me who I talked to. He wasn’t the best looking, nor was he in great shape, but I really enjoyed his confidence and personality. We chatted a bit and then went our separate ways, and I’m pretty sure he kept doing exercises near me to “happen” upon another compliment or quick chat.

After a bit, he walked over to me and handed me his phone number, introducing himself as Sam. He told me he’s flying solo for the next few days and if I wanted to not spend the holidays alone, that we could hang out, watch movies, chat, or whatever. I just smiled, accepted his phone number, and finished my workout.

I got home and there was still a ton of time left, so I busted open a bottle of wine and started reading a book. It wasn’t long before the bottle was completely empty and I wanted another one. Problem was, I was pretty drunk at that point and I didn’t want to drive. I looked up the closest grocery store and since it was already 7:30 on Christmas eve, it was closed.

I had accumulated a pretty big group of Tinder matches by this point, and I put down the book and started messaging them, and of the two that replied back within a half an hour, they both were out of town for Christmas. I had the little piece of paper sitting on my table staring me in the face, so I decided what the hell? I grab it, saw the name and phone number and gave him a text saying “hi, it’s me from the gym, what are you doing?”

He told me he wasn’t doing anything and we started texting back and forth for a bit. I told him I was missing my kids, that I was drunk and in a bad mood, and he was a great distraction. I also told him I was pissed because I was out of wine. He told me he had a bottle of wine he could bring over if I was interested, and without any sort of hesitation, I sent the dirtiest text I have ever sent, even still to this day: “I would literally suck your dick if you brought me a bottle of wine.”

After it hit me what I said, my stomach sank and I wished I could take it back. I saw his response coming in with the three little text dots for what seemed like an hour, only for it to simply say, “address?”

I hesitated for a bit, because at this point I had never brought a guy over to my apartment. But, I was horny and lonely so I gave it to him. He said he would be here in 10 minutes. He was right on time.

I jumped up and started straightening the place up. I keep a very clean, nearly spotless home, so it wasn’t too much work, but I was finishing the dishes when I heard him knock. I opened the door and he smiled, holding out the bottle of wine. I grabbed it and he said “I didn’t do this because of what you said in the text, I’m not going to hold you to it.”

I turned around and walked over to the kitchen while he let himself in and closed the door. I turned and looked over my shoulder and said something like “that’s too bad.” His face got bright red.

We sat down in the living room. It’s really small and I don’t have a coffee table, so we both sat on the couch holding our glasses of (very full) wine. We talked quite a bit, it was a nice distraction for me about not having the kids for the first Christmas eve, ever in their lives. I did most of the drinking, which I’m glad because he drove over here.

I was pretty drunk at this point and I needed to sober up, at least a little, or I wouldn’t be able to head over for Christmas morning with the kids. I asked him if he would mind waiting around while I jumped in and took a super fast shower to try and sober up. He said he wouldn’t mind waiting. I tied up my hair so it wouldn’t get wet, turned on the water, jumped into a pretty cold shower and took a quick one, and it did the trick. I was still buzzed but not shit-faced like I was before.

My level of horny, though, was still a ten out of ten. I decided I was going to continue on this new bold streak. I dried myself off and cracked open the door, peeking out a bit, and he turned his head, saw me and smiled, and then turned back to his phone. I took a deep breath, opened the door all the way, and walked out, completely naked.

I was a few steps in before he realized, and he looked up as I was maybe 10 yards away and his eyes opened huge. He looked like a deer in headlights as I walked up to him, I got down on my knees in front of him and pushed his legs apart. I reached up, grabbing his cock through his sweatpants, and I asked him if this was okay. He nodded and told me only if I want to, he’s not expecting me to do anything for the wine.

I said something like, “good, because what I really want to do is to suck your dick. Is that okay with you?”

He muttered out an “uh yeah for sure” and then I slid down his pants and underwear. Then I asked him if he wanted it fast or slow, because I can do either. He told me he wanted me to go slow, so that’s what I did. I started by kissing up and down his shaft, then slowly taking him in my mouth. Any time I thought it sounded or felt like he was about to cum, I slowed down, making it last longer.

Finally, after quite a while of teasing him faster and slower, he asked me if I could just go faster now. I obliged and continued to suck a little harder while increasing my pace, not slowing down for him to rest. He came while I continued to suck on him, and even though I pretty much swallow it as it’s happening, I can tell that this is the most in terms of pure volume that I’ve ever come across. I think that the half hour or so of slowly building him up really did it, or maybe that’s just him.

After he was done, I did my signature “hold it while I talk to him, then kiss it and lick the tip before letting go” thing I’ve been doing until then (and still now) because it seems to drive them wild.

I was incredibly satisfied with this one. He seemed so appreciative, and I could tell it made him feel amazing, and he asked to return the favor. I was so freaking horny and I just wanted my vibrator. I wanted him to leave. But he told me he wasn’t going to take no for an answer.

I figured that since I was already completely naked, maybe it was worth a shot. I hadn’t really enjoyed it to this point but maybe it was just because my husband was terrible at it. Also, I had never had someone lick me with the lights on, and this terrified me.

I agreed, and told him I had two conditions. He smiled and was all ears. I told him first, we were going to move to my bed. He shook his head in acknowledgment and asked what the second was. I told him I get to suck his dick again afterward and he looked shocked. “You’re going to do that again?” He practically yelled it and I told him he needed to quiet down. He said he didn’t know if he could.

I told him that the next time would be faster, but yes, I really wanted to do it again so as long as we can try, I would be happy.

So, I headed into the room and he followed quickly after. I asked him how he wanted me and he said on my back. I crawled onto the bed, and he practically dove onto the bed and immediately started licking me. I was already really wet but his licking me didn’t feel that great. Even my ex husband did a better job than him. I was considering stopping. I was considering faking an orgasm. Then, he pushed my legs together and pushed my knees up toward my chest and stuck his tongue in my butt.

Holy shit.

No tongue had ever graced my butthole before. I immediately tensed up. He asked me if it was okay, and I said keep going. So then, he slowly started licking me up and down, and this motion like a pendulum swing was just sublime. I started moaning, and then he moved up toward my clit and licked, and while it felt good, I wanted more lower. I think I said something like “stay lower” and he did. After a few more minutes of that, I couldn’t let him continue. I had my first orgasm from oral, and it was from my butt. I didn’t even know that was possible. Like, I legitimately didn’t know.

I patted the pillow, as if for him to trade places with me. He did, and I laid down on my stomach, holding his semi-hard cock in my hand while I started kissing it. He got hard pretty quickly, and I told him that it looks like we might be in business, and through his heavy breaths, he told me yeah.

I told him I was going to go quicker this time, and he said that would be great, so I did. As soon as he was all the way hard, I kept a constant, quick, motion and I started playing with his balls. I hadn’t ever played with any balls besides my ex before, and that was very minimal. But he seemed to like it.

This time, instead of it being around a half an hour, it was just a few minutes. And he didn’t cum very much at all, which is exactly what I was expecting.

We both stood up, and I went and grabbed his clothes from the couch before walking them back to my room where he was still laying on the bed. I tossed them next to him and told him that I hadn’t realized that it was already nearly 1am and that I had to wake up early so I could go see my kids at 9. He took the hint and started getting dressed.

I walked into the bathroom and brushed my teeth, getting ready for bed. He rounded the corner and looked, kind of laughed and told me he had expected me to be wearing a robe or something. I told him I sleep naked, so why not just stay that way? He agreed and laughed again, saying it was no problem to him.

This is the part I hated, because it’s happening every time and I hadn’t yet figured out how to communicate beforehand. He asked if we could see each other again, even tomorrow night for Christmas, and I told him it was fun, I may consider it, but that it was just meant to be a fun night, nothing more. I think it was a little more awkward this time because I was standing there completely naked, feeling cornered in the bathroom.

He said he understood and hoped I changed my mind. We both said our goodbyes, wished each other a Merry Christmas, and I went and locked the door. I turned off the lights and went to bed, setting my alarm for early.

He and I have chatted a few times since then and I am absolutely considering hooking up again, but we haven’t yet.

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Blowjob

My First Car BJ

I had started getting quite a few matches on Tinder by this point, and it was kind of difficult to weed through them all to find someone that wasn’t a complete asshole. Granted, I just wanted to meet them for a few hours, but that doesn’t mean I want to reward someone who doesn’t deserve it.

I was still chatting with 3 or 4 guys pretty closely, and Oliver asked what I was doing that night. It was Saturday afternoon, I was at work, and I had absolutely nothing going on that night. We agreed to meet up at a bar, one I hadn’t ever been to, but it was pretty close to work so that helped a lot. I didn’t get off until 9:30, and we met up right after. He was there when I got there, and he looked exactly like his profile pictures so it wasn’t difficult to spot him.

We sat at a booth and started chatting. This time I couldn’t pretend that I was from out of town or anything, so it was a lot easier to keep things straight. I was working a holiday temp job which was ending in another few weeks, so I didn’t feel like I had to hide where I worked or anything.

Soon, the conversation turned quite sexual. We talked about everything. It was kind of refreshing to get off my chest about how my ex and I hadn’t really been into sex, we were both just mainly co-parents. He told me how his parents had divorced pretty much the moment he moved out, so it was obvious that they had stuck it out just for him. That me realize that we finally did the right thing by separating. The kids seem happier now that both myself and their father are happy, even though it means bouncing between two households that are much smaller than they were used to.

We talked about his past partners and what he liked. I don’t know why, but hearing some of his stories turned me on. At one point I asked what his favorite experience was, and he told me that right out of high school, his girlfriend gave him a blowjob in his car outside of her house, just a few houses over, after a date. They didn’t have anywhere else to go, didn’t want her dad to find out, so they stopped before they made it back.

The conversation went on for a few more minutes, and then the bartender came over to ask what else she could get for us, and I declined, knowing that I needed to drive. He looked at me and asked if I’d like another, or if I wanted to get out of here. I smiled and nodded toward the door, indicating I was ready to leave.

He settled our tab and I tried to hand him some cash but he refused. We walked out the door, and as soon as we got out there, he pushed me against the wall and started kissing me. It was passionate and unexpected, and he didn’t use as much tongue as I had recently become used to.

After a few minutes of making out like what felt like teenagers, he asked if we could go back to my place. I told him we couldn’t. I didn’t want anyone knowing where I live yet, mainly to protect my kids in case something happens, or he gets clingy, etc. I asked him if we could just go to his place, and he kind of chuckled and said it wasn’t an option either, kind of with a sad, embarrassed look. I think he might still live with his parents, or maybe he has annoying roommates.

He looked disappointed. I grabbed his hand and said I had an idea. I walked him back to my car and I got in, he got in the passenger seat. I didn’t know where I was going, but I figured I’d know when I saw it. He asked where we were headed, and I told him it was a surprise.

I only drove for maybe 5 minutes before I found the spot: the parking lot for a big commercial building that has multiple offices in it. There were a few cars sitting in the lot, either people working late on a Saturday or cleaning staff or maybe people who just left their cars there to go out for Friday night and never came to get them. I parked pretty far away from anything else.

I looked over at him, and I could tell he knew what was going on, but he was remaining cool and calm. He didn’t say a word, he just kind of smirked at me. I turned and started kissing him, we made out for another minute, and I started moving my hand down to his pants. He wasn’t hard at all, but after a few minutes of making out and playing with him over his jeans, he got pretty hard and kind of started pushing up into my hand.

I wanted to lean in and start sucking on him, but I don’t know how people actually do this around the center console. I stopped, opened up my door, and got out. He looked incredibly confused, but then I opened the back door and motioned for him to come join me. It was pretty funny how quickly he jumped out of the car and got in the back with me. We started kissing again, and I pushed him back against the door, so he was laying a little bit. I unzipped his pants and tried to pull out his cock, but it wasn’t working as smoothly as I had hoped.

He unbuckled his belt and unbuttoned his pants, and then I was able to slide his pants down a few inches, getting the access I needed. I was on my knees on the floor mat so that he could lay across the seats of my car. I didn’t feel the desire to tease him as much as I did with Justin because we were out in public. This, to me, needed to be a quickie so we ran less risk of getting caught. I wanted to give him head, not go to jail.

That being said, I held his cock with my hand and then quickly let go as I went all the way deep. I did one nice slow suck all the way down and back up, gave a few sucks on his tip, and then just went up and down at a constant pace. He was loud, moaning and saying “oh fuck” about 20 times, before he quickly came. I think the whole blowjob must have lasted 3 minutes.

As he was cumming, I did the same thing I had with Justin, I just kind of kept sucking and eventually very slowly slid my mouth off, still holding his cock when I looked up at him and smiled. He told me he usually lasts longer, so he apologized and I laughed, telling him I was trying to make it quick so that we didn’t get caught.

I kissed his cock and gave the tip one more lick, and then I sat up on the seat so I could open the door. I got out and back into the driver seat while he was pulling up his pants and situating himself. He climbed into the passenger seat a minute later and told me it was incredible.

I asked if it beat the young blowjob he had told me about, in front of his girlfriend’s house, and he laughed and told me it was ten times better, that this takes the cake for the best experience of his life. He asked me how he could thank me, if he could get us a hotel for the night or if we can go somewhere else. I just smiled and told him that him telling me it was the best experience of his life was all I needed.

I drove away, assuming that any second a security car would be driving in, or a cop car with its lights flashing would be rushing in like in every single movie but nothing like that happened. The only motion was that of a few cars here and there on the road.

We drove up to the bar and he asked if we can meet again. I told him that in all honesty I was just looking for a night of fun, and that maybe we can do it again after some time has passed, but as I had told him in all of our messaging that I didn’t want a relationship.

He said it was cool with him, he’d love to do this whenever and to keep his number. I told him it was getting late and that I needed to get up early tomorrow, so he got out and got into his car and I drove away.

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Blowjob

The First Blowjob I Ever Gave

I am writing this post on 2/8/23 about 12/9/22 so I have dated it as such but that’s why I speak in such past tense.

After having my first sexual experience post-divorce with Nate, it really got me wanting more.

As I said in my last post, the sex was fine, but what I enjoyed was the very end, when I could literally feel his orgasm happening in my mouth. I wanted to experience that again. So, I went out with a mission in mind: find an attractive guy to give a blowjob to.

I didn’t know where to even start. I knew people were on Tinder and have had good luck hooking up with people there, so I got the app. I created my profile and I learned to swipe, and I started swiping on people.

It wasn’t as instant as I had expected. It was already 8:00 by now, and I thought “well shit, I guess I need to go actually meet people.” So, I went to a bar a ways away. I didn’t want to be seen really close to my home, so I picked a bar I had heard was popular from some of the younger people at work. I hoped I wouldn’t bump into any of them, and luckily I didn’t.

I walked in and immediately I felt lost. I hadn’t been to a bar in years. Not just because of quarantines and such, just because my ex-husband and I never used to go out. I had absolutely never gone to a bar by myself. I decided I needed to have some sort of a story, one that would be a reason I was here, so I decided to say I was from out of town and I was staying nearby with a friend who wasn’t feeling well.

I ordered a beer and sat at the bar. I had my phone out, was swiping on some people, and a guy walked up and started hitting on me before I even got my beer. I wasn’t interested in him at all, but I was nice and I chatted for a bit. After a while I noticed a younger guy who had come up right beside this older man who was talking to me, he was very fit, attractive, and exactly what I was after. He had dark hair and slightly darker skin, I think he was Hispanic. I needed an excuse to talk to him.

I told the older guy that I was actually meeting the guy next to him and asked if he wouldn’t mind if the new guy could take his seat. The older gentleman took the hint and walked away. The new guy saw him walk away and asked if that was my husband.

I laughed, told him absolutely not, that I was trying to get rid of him and that I had used him as an excuse, and that I hoped he hadn’t minded. He said he was flattered, introduced himself as Justin, and sat down. I told him I was from out of town, that my girlfriend and I were on a ladies trip, but that she got sick so I was out trying to find something to do. I thought this was the best, in case he wanted to go back to some hotel room that I didn’t have.

A few moments later, he was handed 4 drinks, and he asked the bartender for another one. I joked, asking if he was thirsty, and he pointed to a group of three other guys sitting at a booth across the bar. He asked me to come join them, and I agreed. He handed me one of the drinks and gave me a cheers, we touched glasses, and he gave me a quick rundown of each of the people he was with, nothing fancy.

When the drink he ordered for me came, he put it on the tray and we walked to his group. He slid into the booth, and then I slid onto the edge. He introduced me to the group, and we had a great time. It was a bit awkward keeping up a lie but after just a few minutes it hardly got brought up. I had just said I was from a town a few hours away, and unfortunately one of the guys was from there so it was a bit awkward until we got past it.

Eventually the conversations started shifting more and more to one-off conversations, so Justin and I were able to chat one on one a little bit. His attention got called by one of the guys, and he started talking to him. We ordered a few more rounds, and halfway through my third drink, I got bold and put my hand on his inner thigh. He reacted by looking over at me, giving me a quick smile, and then going back to his conversation.

I crept up, closer and closer and he didn’t stop me. Eventually, I felt just the tip of his cock through his jeans, and at that point, he leaned in to me and whispered, asking if I wanted to get out of the bar. I didn’t say a word, I just nodded. He whispered again that he’d get us out of here.

He finished his conversation and said we were going to take off, and his friends said their goodbyes. None of them asked where we were going, I guess it was implied.

He grabbed us an Uber to his place. He said his roommate was one of the guys still at the bar, and he never was done before 2 am when he was with the rest of them, so we had plenty of time. Once the Uber arrived, we got in and I put my hand on his inner thigh again, and he didn’t stop me. The Uber driver kept talking, which was annoying, but the trip was under 10 minutes so it wasn’t too bad.

We walked into his place, it was a small 2 bedroom house that must have been 80 years old, and as soon as the door closed, he grabbed me and we started making out. I was newly experienced in this department, so I swirled my tongue around his. He started feeling up my shirt and unclasped my bra in one smooth motion.

The couch was only a few feet away, so I backed off, walking into the living room. I asked if he was positive we had the place to ourselves, and he assured me. I slid my shirt off, and his eyes lit up and he walked over to me. I pushed him down on the couch, and dropped down to my knees.

I pushed his legs open a bit, slowly working my way up with my hands, and he watched me, complimenting my body. I unbuckled his belt, then his button, and then unzipped his pants. I tried taking out his cock, but his pants were too tight for that, so I started sliding them off. He lifted his body to help. I backed up a bit, sliding his pants off, and then crawled on top of him. He was just wearing his shirt at this point.

He started kissing my neck, and made his way down to my nipples, swirling his tongue on each of them. I had reached down between my legs to grab his cock, and I was slowly stroking.

I slid back down off of him, back onto the floor on my knees, and grabbed his cock again with my hand. I held it while kissing it a few times, and then took him into my mouth. I had no idea what I was doing really. I had sucked my ex-husband a few times, but never to completion. He just wanted to get to sex pretty quickly every time we did anything, so it was only ever for a few minutes.

It just came naturally. I sucked him slow at first, then gradually started increasing the pace. I read his body, the moans and noises he was making, and felt him moving under my grip. It turned me on more than I’ve ever been turned on in my entire life. I wanted nothing more than to slow this down, to make this last for a long time. I started slowing down to prolong it, and his moaning started getting a lot more intense.

Knowing it was happening, I sped back up, and gave another really hard suck while he came. I swallowed while he was still in my mouth, he pumped again a few more times, and I started slowing down my motions. He was getting really loud, and I almost laughed, but I concentrated on how much I was enjoying pleasing him. After a few more seconds of this, when I felt he was done, I slowly slid him out of my mouth, I still held him in my hand, feeling he wasn’t quite as hard anymore, and asked how it was.

He opened his eyes, shook his head, and told me it was unbelievable. I smiled, gave him a squeeze, and then kissed him in the middle of the shaft. He laughed, told me he didn’t deserve that treatment and I assured him that he did.

I stood up, grabbing my bra and started putting it on. He quickly jumped to his feet, grabbing his underwear, trying to convince me to stay. I told him that I needed to get back to my friend, to see if I could help her in any way. He was sweet, he said he’d help me by going to the store with me. I declined, and he asked me if we could meet up again tomorrow. I lied to him, told him that I was leaving first thing in the morning as long as she felt like she could leave.

He gave me his phone number and told me next time I’m in town to call him. He said he’d be willing to drive to “my town” and I didn’t know what to say, so I just said “we’ll see” and gave him a wink. I walked out to the street and waited for my Uber with him standing out there with me. As the Uber pulled up, he grabbed me, kissed me, and thanked me.

I laughed, said he didn’t need to thank me, and got in the car. He was a sweet guy, and giving him a blowjob didn’t settle my desire to give one, it only made it grow stronger. As I was in the car, I halfway contemplated texting him, telling him we could meet up again, but I’m really adamant that I don’t want a relationship right now and I just want to be single. I knew that going back for seconds could potentially create feelings, and that’s off the table.

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.