[MF] What happened when I helped my boss with an errand... | 2016

This is rather lengthy, so I marked where the sex begins.

When I was 20, I had to move back home from college. To make some money while I was looking for a stable job, I ended up returning to work as an after school tutor for my school district. Since they needed more people working at the elementary school, I was placed there. To my surprise, a fellow classmate of was my supervisor. We will call her Naomi.

I should get this out of the way right now. I am white with black hair, a thick beard, and blue eyes behind a pair of black-framed glasses. I am 6 feet tall and 220 pounds. My cock is 5 ¾ inches hard and thicker than most, or so I have been told. Naomi is black with dark brown hair, brown eyes, and glasses. She was around 5 ½ feet tall and curvy. She also has D-cup breasts and a nice ass. We are both 20 years old during the time of this story.

Because she knew who I was and found out that I had been involved with the program since it started, I became her #2 person. We ended up trading numbers to make it easier for her to reach me, instead of her roaming the large school looking for which room I was in. The job took place Monday through Thursday, each day ending at 6 PM. We never really talked to each other outside of work. So I was a bit surprised when a few weeks later, I get a call on a Friday afternoon.

Naomi asked if I was busy, which I wasn’t. She asked if I was able to take her to the grocery store since her car was getting fixed. Since I only lived about 10 minutes away, I told her I will be there in about half an hour. We never really saw each other outside of school or work, which both had dress codes. So I was amazed when I saw she was wearing a red tank top, with a black bra underneath, and a pair of black yoga pants.

The first thing I saw was her cleavage as she leaned down to get into the car. It was deep and the sight of it started turning me on. I also saw that she had a tattoo on her right breast. Since I needed to pick up a few things as well, I decided to go in with her. Throughout the entire store, I ended up just staring at her ass. When she had to kneel down to pick up something from the bottom shelf, I saw that she was wearing a black thong. Thankfully I was wearing a long t-shirt because she would have seen the hard-on she gave me.

We get back to her place and she asked me to help bring in her groceries. As Naomi was putting stuff away, we made small talk. Then, a light bulb turns on in my head. I ask her about the tattoo. She tells me that she got it on her 18th birthday. She then asks if I want to see it. I wanted to say “Fuck yeah I do” but I went with “sure, if you don’t mind” instead.

She pushes the straps to the side and pulls down the right side of her tank top, showing me her breast. The design was pretty unique. It was like a floral meets tribal design. That wasn’t what stood out though. I also saw that she had her nipple pierced. I asked her when she got the piercing done and she said it was also done on her 18th birthday. Without even asking me if I wanted to see, she pulled down the rest of her tank top and took off her bra.

In front of me were the best looking set of breasts I have ever laid my eyes on. It took all of my willpower to keep myself from burying my face into them. She then decided to tease me by shaking them a bit. She asks if I like them, to which I said I did, but with a lot of stammering. She then smiled at me and walked over, giving me a hug and pressing them into me. She tells me to consider that a thank you for helping her out.

Without really thinking, I hug Naomi back and pull her close to me. She then looks up at me and grins. She felt the bulge in my pants and did the cliché “is that a pen in your pocket or are you just happy to see me” line. I felt embarrassed but the voice in my head told me to play along because it could go places. I told her she should find out.

She then places her hand on my crotch and starts rubbing me through my pants. I lean down and kiss her on the lips while she does. I lower my hands down to her ass and give it a firm squeeze. After a few moments, she breaks our kiss, picks up her bra, and guides me towards her bedroom. I sit down on her bed as I watch her. She stands in front of me and runs her fingers through my hair.

She lets out a sigh and confesses to me. She did not expect any of this to happen, but she hadn’t been fucked in months, and now she feels a bit awkward about it. I definitely did not expect this to happen either. I had only planned to take Naomi grocery shopping and go home to nap. I definitely preferred this outcome though. I then placed my hands on her hips and pulled her in close to me. I told her it has been just as long for me, but if she wanted to stop, we could. She smiles and tells me she needs this to happen.

I lean myself closer into her, placing my face into her breasts. I look up at her and gently suck on her breasts. She lets out some soft moans as he pushes my head closer into her. A few minutes go by before she pushes herself away. I stand up and remove my shirt as I watch her kick off her heels and lay down on the bed. I kick off my boots and stand at her feet before joining her on the bed. I hover above her, with my hand rubbing her thigh. Our kiss becomes more passionate.

---SEX STARTS HERE---

I break our kiss and start trailing my lips down her body I stop at her breasts and flick my tongue against her nipple. Naomi starts pushing my head down lower and I stop right at her stomach. I place my hands on the sides of her yoga pants and slowly pull them down, exposing her thong. I stand up and pull them completely off and kneel down between her legs. I kiss her inner thighs before stopping at her pussy.

I part her thong to the side and slip a finger inside her. I start sliding my finger in and out of her, going down to my knuckle. As I pull my finger completely out, I look at her and give it a lick. She has her eyes closed and is playing with her breasts. I grab onto her thong and pull it completely off. She wasn’t completely shaved, but she had a neatly trimmed strip of hair. I then unbuckle my belt and take off my pants. I watch her slide her hand down between her legs and play with pussy as I reached down into my boxers to stroke myself.

As I pull my cock out, she sits up and leans in closer to it, kissing the tip before swirling her tongue around it. I did not notice it before, but she also had her tongue pierced. I moaned her name as I placed my hand on the back of her head, guiding her up and down my shaft. I ended stepping back, forcing Naomi to get off the bed and on her knees. She then looks up at me and slowly drags her tongue against the bottom of my shaft. That feeling and the look she gave almost made me cum instantly. I knew I could not let that happen right now.

I pulled my cock out of her mouth and lifted her up to her feet. I give her ass a slap before turning her around and cupping her breasts from behind. With my cock resting between her ass cheeks, I asked her if anything was off limits. She tilted her head back and kissed my neck as she wiggled her ass against me. She then told me I could fuck her however I wanted.

I gave her ass another slap before I asked her to lie on the bed and spread her legs. She did as she was told. Naomi’s pussy tasted great and I wanted to taste more of her before I filled her with my cum. I kneel down between her legs and drag my tongue against her inner thigh. I then lean in and give her pussy a kiss before slipping my tongue deep inside her. I do not know how long I was down between her legs, but I remember the room being filled with her moans and my jaw getting tired. She eventually squeezed her thighs against my head and kept me in place as she came.

I got myself up to my feet and started stroking myself, watching her. She was breathing heavily while still playing with her breasts. She then got up and sat on the edge of the bed and started stroking my cock for me. She had her own technique about it too, slightly twisting as she stroked, which felt quite nice. When my erection returned, she took my cock back into her mouth. I reached down and played with one of her nipples, pinching and pulling on it as her head bobbed up and down my shaft.

When she started playing with my balls, I felt myself get closer to cumming. I stepped back a bit and asked her to lie on her stomach. She smiled and did what I asked. I grabbed onto her hips and pulled her to the edge of the bed. I slapped my cock against Naomi’s ass before spreading it, exposing her tight ass. I press my thumb against her asshole and she squirms a bit. I then guide my throbbing cock inside her pussy.

First, I teased her by rubbing my head against her lips. She started moaning and slightly lifted her ass up. I then slowly thrust myself inside her, working my way fully inside her. I then started changing my pace, going a bit faster and harder. Her soft moans quickly changed to obscenities and her asking me to go harder. I go harder like she wants and give her ass a hard slap.

As I get closer to cumming, I start slowing down my thrusts but making them even harder. Naomi then starts pushing herself against my thrusts. I just let her take over and I keep spanking her. I eventually cannot take it anymore and I tell her I am about to cum. She looks back and tells me to fill her pussy with it. I then grab onto her hips and return to thrusting harder and faster until I finish inside her.

We both collapse onto the bed and cuddle up with one another. She then slips her hand between her legs and coats her finger with my cum, before bringing it up to her mouth and tasting it. We both pass out for a while. Then I am woke up with a very pleasant surprise…