Click here for [Part 1](https://www.reddit.com/r/gonewildstories/comments/866h0u/mf_what_happened_when_i_helped_my_boss_with_an/) and [Part 2](https://www.reddit.com/r/gonewildstories/comments/86v3ly/mf_what_happened_when_i_helped_my_boss_with_an/).
This story is rather lengthy, so I marked where the sex begins. And for those who are now joining us…
>*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 had D-cup breasts and a nice ass. We are both 20 years old during the time of this story.*
**—PART THREE—**
As I make my way to the bathroom, she stands in the doorway and tells me she wants to take her shower alone. She tells me there is another one on the other side of the house. I put on my boxers, gather the rest of my clothes, and make my way to the guest bathroom.
The guest bathroom was pretty much empty. Thankfully, it at least had the basics for me to take a decent shower. Halfway through my shower, Naomi knocks on the door and asks if I need anything, to which I tell dinneram good. She then says she is going to make us something to eat and asks if there was anything I wanted. I let her know that whatever she cooks, I will eat. After 15-20 minutes, I step out of the shower, dry off, and get dressed. I then make my way towards the kitchen.
When I walked into the kitchen, I saw her alternating between the fridge and the stove. She was wearing grey sweatpants and a matching t-shirt which swallowed her whole. I walked up behind her and wrapped my arms around her waist, pulling her in close to me. I then rest my head on her shoulder and asked if there was anything I can do to help. She turns around in my arms and kisses me gently on the lips before telling me that she has it taken care of. I give her ass a squeeze and a slap before heading off into the living room.
Within a few minutes, Naomi comes out of the kitchen and tells me the food is done. I make my way to the kitchen, fix my plate, and sit down at the table across from her. We engage in light small talk, mostly about people we went to high school with. I then ask her if she has plans for tomorrow. She said she had to be with family for church and she will be gone most of the day. That means that we only had the rest of the day to spend time together.
After we finish up the meal, I end up cleaning up for her. We then go back to the living room and cuddle on the couch. As we sit there and watch TV, we start talking again, this time more about us. We both agree that there is something between us, but the timing wasn’t perfect. Since her aunt was the head person of the tutoring program, she only got the job because of nepotism, plus the fact that she was in college majoring in business management. She did not want anything to ruin that, so we decided to mess around whenever we could and start dating once the job was over in a few weeks.
Our cuddles eventually lead to teasing. She starts rubbing her hand against my thigh while I fondle her breasts through her shirt, noticing that she did not have on a bra. Naomi then straddles my lap and looks down at me, while slowly grinding into me. Instead of taking her shirt off, I took advantage of how loose it was and slipped my head underneath it. She laughs at first but starts to moan as my lips touch her breasts. She then moaned sharply when I took her nipple into my mouth and started sucking on it.
As I continued sucking on her breast, she wrapped her arms around my head and pulled me in closer. She stopped grinding against me but started lightly bouncing up and down instead. I then used my hands to lift her shirt from around my head. As I looked up at her, she kisses me deeply on the lips. We let it linger for a few seconds before she breaks the kiss. She then smiles and tells me she has a surprise for me.
Curious to what the surprise may be, I ask her what it is. Naomi then gets up off my lap and goes towards her windows, closing the curtains. She then turns off the TV and puts on some music. I just lean into the couch and watch her while stroking my cock through my jeans. She has her back turned to me and starts shaking her hips while slowly removing her shirt. She drops it onto the ground and turns, facing me. She then shakes her breasts while slowly walking towards me.
**—SEX STARTS HERE—**
Naomi drops down to her knees and parts my legs, with her hands running up my thighs and stopping at my crotch. She unzips my pants and pulls them down to my ankles, with her finger slowly tracing along the outline of my cock through my boxers. She then leans into my crotch and kisses up and down the shaft while her hands grab onto the waist of my boxers and pulls them down to my knees.
She grabs onto my shaft and starts to slowly stroke it while her tongue teases the tip. She then drags her tongue across every inch of my cock before wrapping her breasts around it. All I could do at this point was close my eyes and enjoy everything she was doing to me. Every now and then, I could feel her tongue piercing tease the head of my cock each time it popped out through her cleavage.
After a few minutes of this, I told her I was about to cum. This did not stop her at all. Naomi kept stroking my cock with her large breasts. When I finally opened my eyes to look, we made eye contact and just stared at each other intently. I let her know I was cumming and she smiled as I released myself all over her breasts. She cleaned herself up by wiping the cum up with her shirt and with licking up what she gathered with her fingers.
She got up off her knees and then sat down on my lap, wrapping her arms around my neck and leaning into me. I asked her if that was the surprise she was talking about. She told me it wasn’t and just grinned at me. She then wiggled her ass into my lap and wanted me to guess. I assumed it was something she was wearing so I asked. She told me it was and she got up and stood up in front of me. I placed my hands on her waist band and slowly pulled her sweatpants down to her feet. She was wearing a pair of purple panties. I stood up, turned her around, and pulled her in my arms, with my hands grabbing and squeezing her ass. I told her that was a pretty good surprise. She then got up on the tips of her toes and whispered in my ear, telling me that wasn’t the surprise.
Naomi gets out of my arms and walks over to the couch, bending over it and shaking her ass. She tells me to come take them off and see the surprise. I walk over and give her ass a slap before I pull her panties down to her knees. What I saw was definitely a surprise. She was wearing a purple buttplug.
She went back to playfully shaking her ass, asking if I liked it. I told her I did while grabbing onto my cock and stroking it again as I played with her ass and pussy. When I got myself fully erect again, I walked over to the bag holding the stuff I bought for this very moment. She told me there was no need for that yet and demanded for her pussy to be fucked first. I gave her a deep kiss before getting behind her and easing my cock inside her already wet pussy.
I grab onto both of her hips and start fucking her hard. Naomi moans my name as I give her ass a hard slap. I start thrusting into her faster while my hand runs up her side and to her breast. I dig my fingers into it, causing her to moan louder than before. The whole time while I am fucking her, I cannot take my eyes away from her plug. Keeping at my current pace, I place my thumb against her plug and push on it while moving it around in circles.
About 10 minutes go by and she finally says she is ready. I pull myself out of her and go grab the bag with the lube and condoms. While I was getting the condom on, I saw her grab our shirts and place them in the couch where we were. When she gets back into position, I give her ass another slap before placing both of my hands on her ass and spread it wide. I grab onto the plug and pull it out, slowly.
Apparently, the plug was definitely the surprise. The end looked like the standard sized plug, but it was maybe 1-2 sizes bigger than the normal ones I have seen. I open up the lube and pour it liberally down her asshole. I then pressed the tip of my cock against her hole and slowly pushed my way inside her. Even with the large plug being inside her all morning, Naomi was still a very tight fit. After a few minutes of easing myself in, I am fully inside her.
As I started thrusting myself inside her, she let out moans that were a mix of both pleasure and pain. I start off slow and start building up speed gradually as I start to feel her loosen up and relax. Over time, the pain in her moans disappears and I keep going at the same pace. My hand runs up her side again to fondle her breast, while her hand runs down between her legs to play with her pussy. We are both breathing heavy at this point and I tell her I am close to cumming. She then tells me to fuck her harder.
I take a deep breath and start thrusting myself harder into her asshole. The pain returns to her moans but I keep going. I also start picking up speed while Naomi moves against my thrusts. She then starts moaning my name and screaming expletives, telling me she is about to cum. I do my best to keep my pace up until she does. When she climaxes, I pull my cock out of her ass and drop the condom down between us. After a few hard pumps of my cock, I end up releasing my load all over her ass and back.
I lie down on the couch and catch my breath, while she turns around and lies on top of me. While we are both relaxing, I pull a shirt from out underneath us and clean up the mess I made on her back. After a few minutes, she kisses me and tells me she is going to take a shower and clean herself up, in which I join her. We ended up staying in there for a bit longer than expected because we could not manage to keep our hands off each other.
When we get out of the shower, I go get my clothes from the living room and then realize it was my shirt that I grabbed to clean off the mess I made on Naomi. She tells me there is a washer and dryer in the utility room that I could use, to which I do. We spent the rest of the day together and we went out to eat for dinner.
After dinner, we made our way back to her place. We made out in the car before we said our goodbyes.
Source: reddit.com/r/gonewildstories/comments/88c0nu/mf_what_happened_when_i_helped_my_boss_with_an
This is the finale. Ended up running out of room so sorry for the abrupt ending.
Pretty much, I went home and slept. I got texts from her Sunday about how her relatives were asking what was wrong with her because she couldn’t sit comfortably. When I saw her at work on Monday, she was still having problems.
There are a couple more stories I can tell about Naomi. I will tell them sometime in the future, but I am already working on my next story. Will have that uploaded here sometime next week.