I was 27 years old and a few months out from a bad breakup. I found out my long time girlfriend was cheating on me when she became pregnant and I knew it wasn’t mine. She tried to insist despite hardly touching me in the months prior and I finally got her to agree to a paternity test.
It left me depressed for a while. My job wasn’t great. I had always wanted a family. So I restarted on my own with my two cats in an apartment I could just afford on my own.
I returned from work one day to a Uhaul poorly parked outside. As I walked past, there was a girl maybe a few years younger than me softly crying on bumper. Frankly, I wouldn’t believe it if it hadn’t happened to me. But I had to ask what was wrong.
“I told them I needed a downstairs apartment. When I came to pick up my key, they told me that they had to change me to a townhouse apartment. When I got here, I find out not only is it upstairs, but it’s two floors and there’s this little staircase. How am I supposed to get my stuff in?!”
She finally looked up at me with big brown eyes. Just as she did so, a tiny voice from behind spoke.
“Hi! I’m Jackson! Hey mommy, where is everyone?”
It turned out to be her 3 year old son. She was a single mom who just left her husband. Everyone who was supposed to help ghosted her. I ended up helping her move her stuff in, she insisted on feeding me, and from then on we became good friends. Her name was Isabelle.
It happened so slowly, I can’t even say when it did. But by summer, we were frequently having dinner together or going to the complex’s pool. She opened up more about leaving her husband, how her ultra religious family cut her off because of it, and I about my issues with my ex. With the two of us just out of bad relationships and despite her attractiveness, I never considered more.
But then one night they were over and Jackson fell asleep on my couch with one of my cats on top of him as we watched old Disney movies. When I saw him out of the corner of my eye, I asked if I should carry him upstairs.
“No, let him sleep.” She said as she stood up. “He’s a sound sleeper.”
She grabbed my hand and lead me towards my bedroom.
“Uhhhh…Izzy? What…”
“Jackson really likes you.” She interrupted with a smile. “And I do, too. You’ve been so kind to us.”
She leaned in for a kiss, and in my confusion I missed. We laughed and tried again after collecting ourselves. As our lips met, there was a passion I had not expected. I relaxed and soon we began to run our hands over each other’s bodies. Before I knew it, we were undressing each other.
I stopped to take in the sight. Her body was tight and tiny. I was in awe of what stood before me. I looked back up to find her face fixed on my cock. I’m nothing to write home about it, fairly normal with some thickness, but I’m happy with what I’ve got.
She laid herself down on my full sized bed. I felt my cock begin to throb as her tiny body was splayed out before me.
“Please go easy on me. It’s been a long time.”
“We don’t have to.”
“I want to. Please?”
“Let’s take it slow. It’s been a while for me, too.”
I crawled beside her and we began to kiss again. Our hands moved awkwardly like teenagers trying to figure out what they were doing. I decided to go for broke while she awkwardly pawed at my dick. I decided to go for broke and slid my hand between her legs and felt the warm wetness.
Izzy let out a coo as my fingers entered her before using her wetness to start toying with her swollen clit. She began to whimper and moan as I rubbed her and lost focus on trying to touch my cock. I kissed all over body, feeling her reactions to my touch. After a few minutes, her hips began to buck and her breathing increased.
“Oh my God. Oh…mmmmmm….yes….oh…oh…Aaaaaaaaaahhhhhh!” Her body tightened on itself. “What…what just happened?!”
“Pretty sure you just had an orgasm.”
“THAT’s what an orgasm feels like?!?!?! In all my years, I’ve never had one.”
“Well then…”
Emboldened by her response, I kissed my way down her body. I could smell her scent as my mouth moved closer to the clit my fingers had just teased. With my tongue, I began to trace across it. First just licking and flicking, then the alphabet with breaks to taste her juices. Her whimpers of pleasures that began to mix with and then became moans was such a turn on. But moreso the writhing and shaking that my teasing caused in her body.
“Oh my God. It’s…happening. Aaaaannnnnnggggghhhh.” Izzy was panting as the orgasm subsided. “Enough…I…I need all…of you.”
I climbed back over her body. She grabbed me in her hand and stroked as she placed my cock in front of her waiting pussy.
“Izzy. Do we need protection?”
“No.” She shifted her hips. “I’m on the pill. And I can’t wait another second.”
With that she adjusted her body, pushing against the tip of my cock. Her hand released as I slid in and grabbed my back. Izzy gasped as I slowly pushed into her. Her pussy was warm and wet and felt amazing on me as I began to thrust in and out of her.
“It’s been so long.” She moaned. “So long since I’ve had sex. But it never…mmmmm…never was like this!”
As much as I want to say I made slow, sweet love to her all night, in reality it had been a long time since my ex last slept with me. And the resulting depression made even masturbation impossible. But I did take it slow, savoring the warm grip she had on me. Time seemed to slow and the only thing that mattered was the sound of our bodies and the moans that escaped her lips.
I held out as long as I could. Longer than I expected, but soon my thrusts began to increase with the movement of her hips. She dug her nails into me as I let my body take over and began to pant.
With a groan, I let loose and my cum began to flow inside her body. I slowly thrusted as her body milked my cock and pulled out of her as I began to grow soft.
Izzy got up after a minute and went into the bathroom to clean herself before coming back to bed and curling up beside me.