My date with a man twice my age [MF] [age gap]

I grew up in a small suburb of Vancouver in a modest family of 5. My parents, and my 2 siblings. When I say modest, I mean it in more ways than one. Culturally – my mom immigrated from China for college and stayed, and my Dad was born and bought up on a farm in BC. We were fairly conservative (not politically), but that we were big on traditions and modesty. To this day, at 23, when I am home I can’t even imagine wearing booty shorts. Or crop tops. Or going out for a run in just a sports bra and yoga pants. But the other modest part of my upbringing was financial. My dad was a manager at a clothing store and my mother a school teacher. For a family of 5, that meant that we were solidly in the middle class.

Whenever I try to think how I turned out the way I am – those two reasons come to my mind. My desire for the things I thought were unachievable shaped me – and shaped my sexual cravings too. I moved to New York for undergrad. At this point I was still pretty sexual inexperienced. I didn’t have the promiscuous high school experience that was promised to me by Hollywood. I had one boyfriend for a short while. But the sex I had with him can barely be counted as sex. That, however, changed soon :)

Barely into the first semester, and I could see the stark contrast between this city and my modest town. The way some girls dressed even just for class made me second hand blush. The way everyone talked so openly about sex was intimidating. I tried to pretend that I was just as sexually experienced as them, but I every time I said so, I could tell that they didn’t quite look convinced.

Unwilling to accept defeat and admit my lackluster resume of sexual exploits, I decided that I would jump straight in the deep end of the pool and show them all that I can also be a slut. I signed up on all dating apps. As luck would have it, the pool that intrigued me the most was the sugar pool. All the men in this pool promised me the life from the movies. Taking me to fancy balls and galas. Buying me the cocktail dresses that I could never afford. Sometimes even taking me on trips with them.

This is where I met him. James. Attractive would be an understatement. He was 6’2, had these piercing light brown eyes that could convince me to do anything he wanted. Short dark hair, a smile that would instantly fill my body with desire, and in extremely good shape – not heavy, but still muscular. Almost the opposite of me – I barely stand 5’3, with long light brown hair, and while I am fit, I am pretty petite. Oh, and he was 38 – exactly twice my age at the time. He was recently divorced and said that he mostly just needed a distraction from that divorce. Someone to fill that void, and to fulfill his desires. Someone to show the world that he can still have whoever he wants. Someone to take to events – so that if his ex or her friends see him, they’ll be filled with jealous. And from the minute we started chatting, I knew that I wanted to be that someone. More than anything I had ever wanted in my life.

Over the course of the next week, we chatted every day. Flirted, talked a little about what we wanted from this relationship, and decided when and where to meet for our first date.

We were going to meet at a hotel restaurant. I imagined it was because it’d be easy for him to take me to a room after drinks. So I was already building up high expectations in my head. This was my chance. To not only show him that I can be a good little slut, but also to prove it to my friends. I even splurged during the week and got a Brazilian wax – I was hoping to get a lot of sugar in the following weeks, so I justified that splurge in my head. I wore my “sexy” underwear – which was just a pair satin black underwear and bra. And a red summer dress. It was a little tight on me – so it showed my cleavage, hugged tightly around my waist, and just barely covered my butt. I wore my roommates red lipstick. All ready to show him that I was perfect to meet his needs.

As I took the train to the hotel, I could feel a few eyes on me. A mix of pride, as well as anxiety built up through me – not used to having this much attention. Yet I kept my mind focused on him. Wondering how he looks in person, wondering what he is like to talk to, and for the most part, wondering how he will want to have me tonight. None of this thoughts helped. In fact, the just made me wet and lose my composure a little. I was extremely nervous as I walked into the hotel.

The maitre d’ greeted me at the restaurant/bar entrance and asked for my ID – filling me with embarrassment. I was only 19 – about to turn 20, so not yet allowed to drink – which meant we could only sit at the general restaurant and not at the bar. But James seemed to have already arranged for that – making me glad that he was comfortable being with someone my age. Without asking me anything, the host looked me up and down, and with a smile said “Welcome Miss Julie, your date is seated at the table in the back”. Just the fact that the host knew exactly who I was meeting with indicated that James must be a frequent customer here. I wondered if he had met any other dates recently. I wondered how many people I was competing with. I resolved that I will do my best to show him that he can stop his search now.

As I turned the corner, there he was. Seated. Already looking at me. Smiling. I could feel his eyes scan my body and I wondered if he could tell how wet I was. He stood up as I reached his table and greeted me with a hug. He looked even more charming in person somehow. Exceptionally well dressed. “Nice to meet you finally” He said as we took our seats. “You look and smell wonderful”.

“Likewise. Really nice to meet you finally” I replied. No man had ever so casually commented on how I smell before, and I liked hearing that. “And I am glad you think so. Pictures on these apps can sometimes be deceiving I hear, but you look even more charming in person”. I tried my hand at complementing him.

“Haha I appreciate it” he said with a laugh. “Same here. I hope you don’t mind me saying this so upfront, but you look incredibly sexy”.

I must have looked the shade of a tomato – especially with that red summer dress because I remember blushing so hard. He was so confident in everything he did. If this was an indicator for how the night would go, I was going to be a very satisfied girl at the end.

We ordered drinks (just a virgin cocktail for me, don’t worry!) as we started talking about our lives. We got along well. I learned that he was a banker turned investor, and his early profits allowed him to live a lifestyle that didn’t need a lot of hands on work. He was already semi-retired, but did attend a lot of networking events.

We ate a light dinner and continued to talk about various things. We talked about sugaring. He said that he had been on a few dates, but was still new to this. I lied that I had been on a few dates too.

As the night went on, I couldn’t get the thought of him taking me home out of my head. I knew if I wanted this sugar arrangement, I had to impress him tonight. I couldn’t let go of this chance. I inched my chair closer to his through the course of the night. He clearly picked up on the hint and started introducing touch gently into our conversations. He brushed against my hands and complemented my soft skin. He brushed against my thigh and said a quick sorry. We kept looking into each others eyes for most of the night. The lust clearly visible in them.

Finally, as our plates were cleared, he asked if I would like to go back to his place. “For dessert?” I asked with a flirty smile. Making it clear to him what I wanted. “For dessert” He replied. We paid the check, and walked out of the hotel together. He held my hand as he led me. I could sense the very slight rush in his footsteps. As if he couldn’t wait to devour me.

He lived just a block away, so he didn’t had to wait for long. As soon as we entered the elevator to go to his loft, he turned me towards him and kissed me. I think I had a mini-orgasm just then, because a wave of pleasure rode through my body. This was very unlike me, and I was loving every second of it. I had always wanted to be a slut, and I was finally getting to be one.

“As soon as you walked into the restaurant, I wanted the night to take us here” he said as we entered his apartment. This place was unlike any apartment I had ever been to before. On the 43rd floor of a luxury high-rise, view of night time downtown Manhattan through floor to ceiling windows, closets bigger than my dorm room. I was getting the hollywood life. Finally.

He was already heading to his bedroom while I was still starstruck by his life. “Julie, come here. Earn your dessert” I heard his voice. The age gap had so easily translated into a dom-sub relationship. He was the one with power and I was there to please him. Maybe that’s how all sugar relationships are. But I was still surprised. Pleasantly surprised.

I could hide my relative sexual inexperience if all I had to do was to follow instructions and cues. As I walked into his room, he was seated at the edge of his bed. He had already taken his pants off and was looking straight at me. Undressing me just with his eyes. His cock was in his hand. Already rock hard. As if even it was looking at me, waiting for me to come over and please it. “Show me how much you’ve been wanting it all night” he said finally. I walked over, biting my lip, already trying to stop myself from drooling as I looked at his cock. It must have been atleast 7 inches. Definitely bigger than the only other cock I had ever seen.

I got down on my knees, placing my hands in his thighs. Took me a second to stop staring at it. I started licking it from the base to the head. All while closely watching his facial reactions. Noticing what he moaned to and doing more of it. I gently took his head into my mouth, and sucked more and more length with every bob. I maybe have been inexperienced, but I knew what I was doing here.. I had practiced on my dildo and watched tutorials the whole week. I could see his shaft turn red from my lipstick. As I tasted his precum, I looked at him and smiled. He tasted genuinely nice. I could sense his cock gently throbb.

“God that feels so good” he exclaimed. “Come here. I want to taste you too” directed me to stand up. He stood up himself, his cock still in my hand as he put his hands around me, found the zipper to my dress and pulled it down. My dress slipped down to the floor as if even it was following his commands. “I have been wanting to see this sight all night.” He picked me up with ease – our size difference quite apparent, and laid my down on the bed. His hands moved up my legs, already making me slightly shiver, and gently pulled down my panties. He took a quick sniff, looked me in the eyes “You’ve been a horny little girl all night, haven’t you Julie?”

As if I had forgotten all words, “MMhmm” is all I could come up with. I was already soaking wet and he now knew how badly I had been wanting him all night. “Let’s see how the dessert tastes”.

I have never felt so good in my life as I did next. His tongue, his fingers, his lips. He played with my clit, teased me, bought me to the edge and stopped, did that again, and again. As if he were just toying with me. Playing with me. It’s because he really was. For what it was worth, I was his toy when I was in his bed. That became clear right then, and stayed that way through the course of our relationship. When he had ensured that I was as wet as I could be without orgasming, he stood up, picked me up again, and turned me on all fours. He entered my pussy from behind, his cock entering me slowly at first and then increasing its pace. Sliding more and more length in my tight wet pussy with every stroke. All 7 inches eventually thrusting in and out of my tight body. A sensation I had never experienced before. His hands moved up my body and grabbed my hair as if he needed a grip on my body. He pulled me back towards him, now just on my knees and continued to thrust in and out of me. He kissed my neck as I realized I couldn’t control my body any longer. I had lost all control over it, and I could feel the orgasm coming. The sensation building up in my body. And I was too lost in the moment to tell him about it. He continued to fuck me in that position as my wet juices gushed out of my pussy. My body trembled and I came all over his cock as he continued to fuck me through it.

He put me back down on his bed as I continued to moan and tremble.. still recovering from that orgasm. “Good girl, Julie”. I can still hear those words when I close my eyes and masturbate. “Now turn around for me. It’s time for your dessert”. I turned around, laying on my back now. He got on the bed, and climbed up on top of me. His knees next to my torso as he straddled my body and aimed his cock on my face. “Finish me off over your pretty face” were my last instructions for the night. I freed my arms from under him and stroked his hard throbbing cock. I looked at him, my eyes begging him for his cum, and was rewarded with a thick white splash soon. And more and more ropes spilled out of his cock and covered my face. He moaned through it. That was my very first facial ever. And now I can’t stop wanting them.

In a way this relationship taught me a lot about my own sexual cravings. It was as if he already knew them somehow and just showed them to me.

(PS: The base premise of this story is actually true and was my first ever sugar relationship (I’m 23 now). Although a lot of the details are exaggerated to make it better suited for erotica :) If you enjoyed reading this and would like to hear more stories from me, please let me know! <3)

Source: reddit.com/r/Erotica/comments/vbp3um/my_date_with_a_man_twice_my_age_mf_age_gap