I’m in my mid-30s, single, living in the Toronto area, white, professional… and I have been a sugar daddy for several years. Why I do it is just plain old satisfaction and sex. I get a nice companion, they get the help they need. I was engaged in my mid-20s and we had a very bad breakup a month before the wedding. It jaded me on dating and I let my career take over my life for the next few years. When I realized I needed someone in my life I no longer had time to find anyone. Then I started to read about being a sugar daddy, and it seemed to fit my lifestyle. I decided to give it a shot. I’m writing this story about meeting my first sugar baby for the first time.
I’d found her online. Screenname “BadBobbie” had contacted me via direct message first. My profile had made it clear I was looking for a physical arrangement, she was looking for the same and needed a good lover. She was described as 5’6, brunette, brown eyes, 34B-30-33, 22 years old, student, a college sugar baby.
We worked out an arrangement and talked some more to make sure we both were right for each other in this. We decided to meet at a busy chain coffee shop near the subway. She was going to wear a jean jacket and black skirt. I got there early, heart racing…
Would she actually show up? My watch ticked on to the time of the rendezvous, no sign of her. I tried to calm my nerves but my mind was racing and adrenaline pumping. About 10 minutes later I got a text from her saying her subway had been delayed but she was walking out of the station would be there in a minute.
I sat staring at the door like a deer caught in a semi’s headlights. Sure enough, faded blue denim jacket, black skirt to just above her knees, long brown hair to below her shoulders. I got up and got near her, not easy due to the busy nature of the place. Called her by Bobbie, she heard me, turned and smiled. It was her, exactly as the pictures online had been.
We got her a coffee and had a chat. Her real name was Tracy, she had the sweetest little whisp of an English accent, she said it was because both her parents were from England, and still spoke with an accent, but she tried to hide it.
After she finished her coffee I asked her if we could go to a hotel nearby. She looked at me quizzically and said “well I guess you aren’t an ax murderer, so why not? Let’s go have some fun!”.
I drove us to the hotel, got us a room. When we got there she excused herself to the bathroom. I waited patiently sitting on the bed like a giddy teenager. I hadn’t felt so excited and nervous in years.
She came out in a matching blue lace bra and panties combo.
“Like what you see?”
I couldn’t answer, my mouth was on the floor I think. She just giggled and came over to me. We kissed for the first time, lightly at first then mouths opening, tongues swirling around each other. She broke the kiss and looked me in the eyes, then started undoing my belt.
I leaned back and let her work. She got my pants down, then massaged my cock through my boxers. I pulled my shirt off and watched her working her hand into my underwear, finally making skin contact with my semi-hard member.
She pulled my boxers down and started working my shaft. She got on her knees and gobbled my cock into her mouth all at once. I was harder than I’d ever been in my life. She bobbed her head like a girl on a mission, I didn’t hold out long, i felt the itching pressure deep inside my groin. I warned her I was going to pop, just moaned on my shaft and kept going. I erupted into her mouth, she took it all and swallowed it.
She stood up, smiled and got next to me on the bed. After a few minutes to recover I moved over her, kissing her again while fondling her tits through her bra, before slipping my hands under her and unclipping it. Her firm small tits were wonderful in my hands. I sucked her pink nipples hard and played with them.
I moved a hand down to her panties and began tracing her slit through the fabric. She moaned as an applied pressure to it while flicking my tongue over a nipple.
I slid my hand under the elastic of her panties and touched her wetness for the first time. She was so soft and moist. Totally bare not a hair or stubble I could feel. I kissed her again then moved myself to kneel next to her. I pulled her panties down and enjoyed the sight of her naked body. She was hairless from the waist down, not a sign of stubble on her mons or legs. I smiled at her, got between her legs and lowered my mouth onto her.
I started licking her slit, tasting her, then parted her with my hands and started working her clit with my tongue. She let out an “oh gawd yes” cry as I flicked it up and down, back and forth. As she got into it I inserted a finger into her, then a second curled them up and found that wrinkly spot at the top of her love canal. I started stroking it while I continued to lick her button. She started to cum, I kept going, and she just kept rolling. She bucked and thrashed like a wild animal until she pushed my head away, catching her breath.
“Where did you learn that?” she asked me…
“I just knew how somehow” I replied as I winked at her.
We lay there side by side for a few minutes cuddling each other. She finally got a response out of my cock, getting me up again. She picked up a condom, rolled it on me. It was time for the main event.
She straddled me, leaning back slightly and rubbing my cockhead up and down her slit before lifting herself and sinking down on me. She took my cock all inside her and slowly started to rise and fall. My cock felt her insides squeeze hard as she moved. She started to go faster, her tits bouncing up and down, and hair falling all over her shoulders and upper chest.
She kept this up for some time, but then got off, rolled onto her back and said “your turn lover”. I got between her legs, slipped my cock back inside her and started pistoning in and out of her. She started to cry out yes as I slammed myself balls deep in her over and over.
I felt myself getting close. She had told me she had had the birth control shot but I still didn’t want to take any risks on our first meeting. I pulled out of her, slipped the condom off and started jerking myself. She said, “come up here, I want to on my tits, cum for me”.
I knelt next to her, had her push her globes towards each other. I came hard splashing across her nipple and into the valley between her breasts. I flopped down spent after the last shot splashed on her breast. She giggled again and went to the bathroom to wash up.
She came back out after showering and laid back down next to me, we kissed again and amazingly i felt myself getting hard for the third time. She looked down at my hard cock again and said: “I’m that good?”. I just laughed and so did she.
She started slowly jerking me with her hand and then asked me how I wanted to do it again. I said “Doggie?” She smiled, got up on her knees and swirled her bottom around seductively. I rolled another glove on my cock and slowly inserted myself into her still soaking wet hole again.
This time I went slow, enjoying the sensation of her silky insides against my cock as it moved in and out. I sped up as I started to feel that familiar itching and finally had to stop before I popped again. I pulled out of her, asked her to lay down on her front, knelt with her ass under my thighs and jerked myself onto the small of her back.
I told her not to move, went and got a towel and carefully cleaned my cum from her back. She purred that it felt so different and good, no one had ever cum there before.
We showered together, not sexually just as a happy pair of bodies washing each other. We dried off, got dressed and I took her back to the station after fulfilling my arrangement with her.
We were together for 2 years after that. We pushed each other’s sexual boundaries and explored a lot together. If you want to hear more about my time with Tracy, or about my later sugar babies, comment nicely on this 😉
For more reading: My Real Story of Being a Success Sugar Baby