I have been navigating the past months of being single after a bad breakup. It has been months since the breakup but only recently, with some help, have I regained my self-esteem and confidence.

It started simple enough, I met eyes with a great looking woman at a coffee shop, struck up a conversation, and got her phone number. The date never panned out but I realized that women were finding me attractive again. The next week, same coffee shop, different woman, the date was fun and the second date was "more fun." My confidence had been restored.

The following weekend, after my date cancelled, I was doom scrolling on Instagram that Friday night and a post from a friend caught my attention. I do not know this woman personally, but know of her, we leave near each other, have one hundred mutual friends on the app, and became connected on the app a few months ago for those reasons. That night, she had posted a selfie and she looked gorgeous. I know she is a few years older than me; I remembered her posting photos of her 50th birthday party a few weeks ago, but she looked great.

In the photo, her hair and make-up looked fantastic, she had great cleavage, and her outfit was sexy. I opened her profile, scrolled for minutes before finding a man in any of the photos, and thought that she might be single and/or recently divorced like me. In that moment, I decided to send a DM. It read:

"Hey, I noticed your photo tonight and you look great. I do not know if you are dating but I would love to take you for drinks or dinner sometime. Let me know."

She replied very quickly, "Oh my goodness. Thanks, sweetie. Unfortunately, I am married, but if I were single, you would be picking me up for a date tomorrow! Thanks so much!"

I replied, "I am so sorry. I had no idea you were married. My apologies. Have a great weekend!"

She replied, "Sweetie, no need for apologies. You made me feel seen, and I'm touched," with a heart emoji.

The next day, around lunchtime, she posted another selfie, this time in a bikini by her pool with the caption, "Wine and compliments make a girl feel really good. Thanks, sweetie!"

I was perplexed by the caption because she called me sweetie two times the night before. I put a like on the photo and, within minutes, received a DM that said, "I was hoping you'd notice my picture and caption today. Thanks, sweetie."

I was confused, but I replied, "How couldn't I notice? You look incredible."

She replied with the blush face emoji, heart emoji, and the whisper (shh) emoji and said, "if you keep hitting on me, you're going to get me in trouble!"

I shot my shot again and said, "I think you want a little trouble. Let me know if I'm right."

She replied with the blush emoji again and said, "Ugh, you're trouble. Maybe I do want trouble."

I said, "I'm around. Let me know."

A few days later, on her last day of work before summer break, she posted a selfie, she had on sunglasses, makeup was done really well, a shirt with lots of cleavage, and a glass of wine with the caption that said, "Last day of work before summer break starts. Looking for trouble! Who's in?" She added some hashtags and things, but I knew she was communicating with me. I liked that picture and got another reply from her: "Hey trouble!"

Another few days went by and she posted a picture from a restaurant nearby. She was dressed up nicely, and the caption said, "Need some attention. Hubby barely noticed the new outfit I bought for dinner! Ugh!"

I liked the picture and sent a message, "I certainly noticed it. I have another outfit in mind for you when you're ready for trouble."

She replied, "Oh my goodness. Out of curiosity, what does your outfit look like?"

I said, "Lots of lace, and will match any floor it winds up lying on."

She replied, "Ugh. I am ready for trouble. Will you help me find it?"

I said, "You've found it, I'll plan it, and you'll really enjoy it."

I received the blush-face emoji, she "shhh-face" emoji, and the kiss-face emoji with this message: "Let me know what you come up with...I'm expecting lots of lace as promised."

I sent her a message the next day and said, "What day works? We've taken the flirting as far as we can both manage."

She said, "Sunday. I have to take my husband to the airport, and my kids will be away at camp."

I booked the room, upgraded it to one of the rooms with a jacuzzi tub, and bought the outfit I wanted her to wear. I sent her a message that night that included the details and a picture of what I bought her and in the message, I said, "This is going to look great on you for as long as it stays on..."

She replied, "Oh my god...so excited...see you Sunday, trouble."

The morning of our date, she posted a photo of a coffee mug on her porch with the caption, "Hubby and kids all gone for the week! What's a girl to do? #trouble jkjkjk"

I liked the photo, and she messaged me, "see you soon, sweetie. #trouble"

She messaged me later that afternoon, saying that she would be at the hotel around four but would need time to freshen up.

She showed up, I let her in, and laughed at myself regarding her outfit. She had on a tank top, sweatpants, her hair in a messy ponytail, and flip-flops. She was carrying a large bag over her shoulder. I handed her a glass of champagne, and we kissed for the first time. Then the second. Then she put her hand up to my mouth and said, "Wait. I need a favor. Will you allow me some privacy for 30 minutes? I want to freshen up, do my hair, my make-up, enjoy this drink, and put your outfit on so I can see your face the first time you see me in it."

I said, "Sure. Take your time. I will be downstairs. Message me when you're ready."

I went to the bar downstairs, ordered a drink and waited for the message. Finally, about forty minutes later, a message popped up on my phone.

"This is so exciting, and terrifying, and I'm ready for you to come up and give me as much trouble as I can handle."

I said, "I'm on my way."

I got to our room and swiped in. As I turned through the small foyer, I looked up, and she was standing in front of the window, next to the jacuzzi, with her hands on her hips, wearing the outfit I purchased her and a pair of black stilettos that she brought in her bag. Her hair looked great, her make-up was perfect, she was smiling big, and said, "Well?"

I said, "I had the highest expectations, and you somehow exceeded them. Oh my god."

She ran to me, and I took her in my arms and squeezed her ass as we kissed deeply. I moved her over to the bed and sat her down. She looked up at me as I bent down to kiss her again. I grabbed her hand, kissed the back of it, and placed it on my belt buckle as she stared up at me. She took her other hand and rubbed my crotch outside my pants without breaking eye contact with me. Then she said, "Let's see how much trouble I'm getting into tonight."

She unbuckled my pants, shoved them to the floor, and then took my boxer briefs by the band and pushed them to the floor as well. I stepped out of both and watched as she stared at my dick. I put my hand on her chin, lifted her head up towards me, and kissed her again before whispering, "Is this enough trouble for you?"

She smiled and said, "It's more trouble than I've ever had" and before I could reply or kiss her again, she took it in her hand and guided me into her mouth. She swirled her tongue around my cock while staring up at me. Then she looked back down at my dick as she took all of it in her mouth and started slowly bobbing her head up and down along my shaft. I gently rubbed her breasts as she continued to suck me off. I was getting closer to Cumming as she massaged my balls and took me even deeper into her mouth. Finally, I let go and blasted the inside of her mouth with my cum. She looked up at me as she swallowed my cum. I wiped some remnants off her chin and cheek and bent down to kiss her. Then I knelt on my knees in front of her and removed her bra as we made out. I began kissing and sucking on her breasts as she bent her head backwards and moaned softly. Then I gently nudged her so her back was on the bed while I kissed her stomach down to her mound and further to her inner thighs. I peeked up over her body and caught her eye as she was staring down at me with a seductive smirk on her face.

As I nibbled and kissed her inner thighs and took in her scent, I peeked up again and said, "I'm so happy you're here with me" and as she was saying something, that I couldn't make out, I swiped my tongue from bottom to top of her slit and teased her by saying, "What was that?"

She giggled a bit and said, "I'll say it later," and pushed my head back down. I sucked and licked her clit as my fingers massaged her insides, and her hips thrusted up and down to mimic my fingers' movements.

Between moans and sighs, she muttered, "This is soooo good" and "Please keep going," which only turned me on even more.

Within minutes, she was pressing her hips upward as my tongue stayed fixated on her clit and she let out a long, dramatic gasp and a subdued "Fuck yessssss" as her hands fell from the back of my head back to the top of the mattress.

I lifted my head, then my body, and crawled up on the bed so she was effectively trapped under me and kissed her again. We used lots of tongue as I lifted her hands and arms above her head into a more submissive position.

As I pulled away from her, I said, "Have you had enough trouble yet?"

She said, "Not even close. I want you in me now. NOW."

I pressed my hips down and entered her hard. Her eyes got wide, and as she grabbed the back of my head, she said, "Oh fuck. You're on my cervix already. Do it."

So I pressed a little deeper, pulled back, and pressed in even harder. I watched as a serious look came over her face, her head turned to her left shoulder, and she muttered/whispered, "Fuck me, sweetie, just fuck me."

I did as she said and pounded away in her. Hard strokes where I penetrated her as deeply as I could and stared at her and watched as her face became flusher and her looks bounced between feelings of absolute pleasure and serious desire."

A few minutes later, we both climaxed at the same time and slumped together in a pile. A few seconds later, we both giggled together, and she said, "Honestly, I've never been fucked that well. Holy shit."

I said, "I don't believe you."

She rolled over to face me, placed her hand on my cheek, and said, "I'm serious. My husband and I were both overweight until recently. I had a health scare two years ago and lost like eighty pounds. He hasn't lost a pound. He barely looks at me anymore, let alone touches me. This was so great..."

I stopped her before she continued and kissed her again, and when I pulled away, I said, "We don't have to talk about him tonight. Tonight is about us. Let's have some more champagne and get in the jacuzzi."

She smiled at me, kissed my cheek, and said, "Yes! Are you ok with me taking this off?"

I said (sarcastically), "Oh no... will you be naked?"

She laughed and said, "Yes, until tomorrow when we leave, jerk!"

We both laughed together as we stripped and poured our champagne and got in the jacuzzi tub. She snuggled into me and while we were making out, she ran her hand up my leg and began jerking me off. Between her hand, the hot water and bubbles, champagne, and kisses, we were both in heaven.

The jerking became more intentional, and she whispered in my ear that I should stand up. I did as she asked, and she put me back in her mouth to bring me to completion again. I sat back down, took a sip of my drink, and said, "I am so glad we got to do this."

She said, "I'm so glad we have all night to do this."

We sat there silently for a few minutes just enjoying each other's company and our surroundings. Then she stood up and sat herself on my lap. She positioned herself so her tits were in my face and asked me to kiss them like I had earlier on the bed. While I was doing that, I subtly grabbed her hips and slid them forward so I could enter her again. She straightened her back as I entered her, looked at me, bit her lip, and said, "I've never done it in water."

I said, "Now you have."

She smiled and slowly grinded her hips on me. Within minutes, we were both cumming again.

She stayed on top of me and said to me, "I told you earlier about my weight loss and stuff. Tonight is so special to me. You've made me feel so good."

I said, "Have you had many partners?"

She said, "Haha, no. You're the third man I've slept with."

I said, "Shut up. That can't be true."

She said, "No, seriously. I had a boyfriend before I met my husband. He was my first. We broke up when I was in college. I met my husband while I was in graduate school, and I have been with him since. We are in a relationship of convenience at this point. There was never much intimacy but there is none now. I have lost all this weight, I thought he would find me more attractive, but it has almost had the opposite effect. That's why I post so many selfies. I had been craving attention and positivity and, until you messaged me, I hadn't received any."

I placed my hand on her thigh and said, "I'm glad we're together tonight. Was there anything you came here wanting to do? Like, specifically, was there something that you've never done but want to, or fantasized about, anything?"

She bit her lip again and said, "I came here tonight hoping for passion and orgasms. Real orgasms. Fantasy is what we're doing. I wore lingerie and heels, in an expensive hotel room, with a handsome younger man and champagne. I'm so content right now."

I said, "Well, that makes me feel good. Let me say it differently: what have you fantasized about that you have never done in bed?"

She said, "Don't laugh."

I said, "I would never."

She said, "When I'm home alone and masturbating, you know how those movies end."

I said, "A facial?!"

She said, "Yeah, I mean, I've always wondered if sex could actually be good enough that I'd ask for it anywhere on me let alone my face. Until tonight. When you had me on my back earlier, I wanted it badly. I almost asked you for it when I blew you here in the tub too...Oh my god, I am so embarrassed. I cannot believe you just got me to admit that. I need more wine! Get me more wine!"

I looked at her for a second and said, "That's my biggest kink."

She stared at me for a second and said, "Really?"

I said, "Yeah, my first long-term girlfriend was really into receiving them, she had a major cum kink, and I developed a kink for giving facials."

She kissed my cheek and said, "I may let you. Where is my wine! I was not kidding!"

I laughed and got her more wine. Then I helped her out of the tub, and we lay together on the bed.

While we were spooning, she said, "What's your body count? I'm not going to judge. I'm just curious."

I said, "Sixteen with you."

She sighed and said, "I'm sort of jealous of that."

I said, "Don't be."

Before she could reply, I grabbed her and rolled her onto her back and got on top of her. She opened her legs, and I entered her once again. I pressed myself as deep as I could into her and we had deep French kissing. I began fucking her with hard, deep strokes, and I could tell she was on the verge of another orgasm.

While she was cumming, I was doing everything to hang on, and she said, "Do it. Do it. Do it!"

I pulled out, sat up, and released on her. She had cum on her face, tits, and stomach when I was finished.

She smiled at me and said, "I think I get it now. That was actually hot. Can you get me a towel, though?"

When I walked back to the bed with the towel, she sat up, took it from me, and I said, "Was it actually hot? Did you enjoy it?"

She said, "Yes. It was like a feral moment. I watched a man give me an orgasm, and I gave him one, and the proof landed on me. I see why that girl had that kink now. Ugh. It's going to be hard not thinking about tonight forever."

I said, "What's hot is listening to you talk about it. That's hot. You're freaking hot."

She grabbed me, kissed me, and said, "Fuck me again."

I smiled at her, put my hand under her armpit, and flipped her over onto her knees. She looked back at me and winked as I entered her once more. I started pounding away at her and then got bold and started rubbing her asshole with my thumb and said, "It's going in."

"Just do whatever you want. I'm all yours."

I put my thumb in her ass and watched as her back arched down and her head popped up. She was rolling her neck and muttering as I pounded away and fucked her ass with my thumb. Then she said, "I am having another one. My god, I am having another ONE!"

And I smiled and watched as her legs and ass spasmed. She collapsed onto the bed, face down, and did not look up but said, "Did you cum?"

I said, "Not yet."

She rolled over and motioned for me to come back to her mouth. I put it in her mouth again and, once more, she sucked me to completion. When I came, she lay down on her back, and I got on top of her and gently kissed her neck and shoulders while she caught her breath.

She said, "I am so sore."

I said, "I bet."

She said, "I think we need to rest for the night. My girl needs a break."

I said, "That's a good idea, but don't be mad if I wake you at like 2 or 3 am for another round."

She smiled and kissed me and said, "I'll be mad if you don't. I am really excited for early-morning sex, though, too. Don't remember the last time I've had that."

I smiled and kissed her and said, "I'm really excited for my early morning blowjob and sex. That's the best way to start the day."

She playfully hit me and said, "Of course. That was implied. It was also implied that you'll be going down on me too."

I said, "Of course."

We fell asleep shortly after, and it was the best sleep I've gotten in years. Neither of us woke up until the sun started shining through the blinds in the morning. She rolled over, we kissed a few times, and she said, "You should go downstairs and get us some coffee. Then I'll sip on my coffee while you kiss me all over and eat me out."

"I like that plan."

She said, "Before you go, though, I should pay for my coffee."

I said, "It would be the right thing to do."

She smiled at me and went down on me. I watched this woman take me in her mouth again and suck me to completion in the greatest way.

I kissed her, got my clothes on, and ran downstairs for our coffee. While I was down there, I stopped for a second, just sat on a chair in the lobby, and pondered for a moment how absurd and exciting the last 12 or so hours were. Upstairs, in the room I paid for, a hot, married, older woman had allowed herself to be vulnerable and let me help her explore her sexual fantasies. I was sad it was ending, but determined to end it positively.

I walked back upstairs with our coffees to find Kathy, wearing her lingerie again, standing there waiting for me. We kissed, and I whispered to her, "You look so sexy in this outfit."

She said, "Thanks. There's one more fantasy we need to check off, and I wanted to put this back on for it."

I said, "What's that?"

She said, "I want you to hold my phone while you fuck me. I want a video of me getting fucked. I want it to be me when I masturbate. Will you?"

I said, "Are you going to send it to me?"

She said, "Of course."

I said, "Then of course I will."

She handed me her phone and lay back on the bed. I started to go down on her and handed her phone back. She held it and recorded me eating her pussy and then handed it back to me as my cock entered her. I recorded her facial expressions and the POV of my cock going in and out. I was so hard because I was so turned on. When I came, I gave her a cream pie and zoomed in on it as it leaked from her insides and turned the recording off.

We lay together and made out off and on for an hour before she said, "Ok, sweetie. Let's get a shower and get out of here."

I said, "Together?"

She said, "Yes, sweetie. Together."

We explored each other's bodies yet again in the shower. My cock found her mouth, my mouth found her pussy, and my cock entered her for the final time. We came together; we laughed and then helped each other dry off.

We each got dressed and made out again and walked out of the room together. In the parking lot, I held her hand briefly and said, "Let's stay in touch. I hope this wasn't the last time we're together."

She said, "It isn't. I like trouble, sweetie."

Later that day, while recovering, I opened Instagram, and the first picture in my feed was Kathy. She was sitting by her pool, in a bikini, glasses, holding a Diet Coke, and the caption read, "Love this sunshine. So relaxed. Watching a movie on my phone and thinking about my sweetie!"

I put a like on the picture, got the heart emoji in a message, and went on with my day.