By June 2018, I had a slight reputation amongst a few women at my store. I didn’t mind, but the past year had been very adventurous thanks to Ashleigh. It was the anniversary week of Ashleigh and I’s first night together, and I was working in the online pickup department. They were short-staffed that week, and I was helping for a few days.
One of the ‘pickers’ (picked the items ordered off the shelves) over in the department was Shelby. She was cousins with Victoria (from Victoria: I’m 19 Now), and she was nine days younger than her. Their mothers are sisters, so that had to be an exciting time for their parents. But I digress.
Shelby and I had always gotten along well. She hired in around the same time as Victoria, and like her cousin, we went to the same high school just not together. We especially talked during basketball season as both of us loved the sport and talked about games, coaches, and funny practices.
Now Shelby was a natural flirt, and I know for a fact she fooled a few baggers on multiple occasions. Sometimes it was on purpose, and other times it was merely the baggers misunderstanding. I knew better and was aware she had a boyfriend. She and James had been steadies since their sophomore year of high school.
Shelby, like Victoria, was very attractive and had a body that was difficult not to want to appreciate. She was about five-feet-seven and had a moderately toned athletic body. Her breasts were about a 34C, and her skin was tan from a recent week in the sun. Accompanying her glowing smile were brown eyes that could be distracting if you weren’t careful. Her hair was pitch black and hung to the middle of her back. Her butt was not what everyone would call a bubble butt. However, it was well proportioned, and I would say it was one.
As I mentioned, Shelby had just turned nineteen on May 11th, and it wasn’t long after that day that Victoria and I had our little fling. Shelby had never flirted with me as she did with other guys, nor did she ever confront me about what she had heard from a few of the other women in the store, because I know there was no way she hadn’t. But after my day with Victoria, it wasn’t long after that Shelby did turn up the flirt levels with me, and this continued for three weeks or so until the day.
That takes me back to the week I was helping out the online pickup department. I had a morning shift, so I had arrived at six in the morning. Shelby came in two hours later, and we were both ‘pickers.’ It was about noon, and I had just returned from my lunch break when we were alone in the department room.
“So, I heard about that pool party with Victoria,” Shelby said as she looked over her shoulder as she stood by the computer.
I was sitting down, retying my shoe, and said, “It was a fun afternoon. The sun was nice and warm…”
“And your cock was in Victoria’s warm pussy,” she cut me off and smirked. As she did, she turned and cocked her hip.
“It may have been,” I smirked back at her. I was now wondering if she had heard about last Saturday night, too.
Shelby looked at me without skipping a beat despite seconds ticking by. It was as if she was sizing up a play on the basketball court.
“So, I’ll get right to the point since we may not be alone for much longer. James and I have begun to explore some boundaries lately, and a threesome is one of the items on our list,” she chuckled at her statement as if it were merely a bucket list of places to visit. “I’ve heard of some of the fun you have had, and after hearing some things from Victoria, I was wondering if you may want to join our threesome?”
I made a slightly surprised face and said, “Really?”
“Yes, really. But the only thing is that I would only blow you,” Shelby began. “James isn’t sure how he feels about another guy's cock fucking my pussy, and we both won’t do anything that we are uncomfortable with.”
Truth be told, I’d never been in a threesome either, and even if I was just getting a blow job, it put a light checkmark next to a box for me. It sounds terrible, I know, but hey, I’m not going to turn down a blow job from Shelby if she invites me to.
“Okay then, when were you and James thinking?” I asked.
“How about this evening? His parents left this morning for a wedding in Los Angeles, so we have the whole house to ourselves. I get off at 4:30 p.m. I have your number; I’ll text you his address, and why don’t you show up at six?”
“That will work for me,” I nodded and smiled.
“Great!” Shelby pulled out her phone and texted me James’ address. “Okay, sent!”
Just then, Micha walked in. She was the supervisor that day for online pickup and said, “Sent what?”
“I just sent Jack a wild basketball highlight clip that he has to watch after he gets off work,” Shelby responded.
“Paaa,” Micha remarked. “Basketball is dumb. Play soccer instead,” and he walked to the computer.
Shelby and I exchanged looks of ‘basketball isn’t dumb’ and ‘that was a close one’ before heading out the door to pick some orders.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
I didn’t even have a chance to ring the doorbell when Shelby opened the door. She was wearing a thin black coverup over her floral bikini.
“Welcome to the party,” she giggled, not nervous at all for the reason I was there.
“Hey… you didn’t tell me to bring some swim trunks,” I said with a playful pout.
“Last minute decision,” she explained. “James has a spare pair you can use.”
James’ parents had a big, beautiful house, which included a pool house in the back. Shelby led me to a bathroom, and James rounded a corner ahead
“Hey, Jack, welcome. There is a spare pair of trunks on the countertop in the bathroom. See you in the pool,” James said as Shelby, and he turned to head out. He also gave her ass a good smack on the way out, making her squeal and giggle.
A few moments later, I emerged onto the patio wearing the trunks. James and I were about the same waist, so at least they fit.
“Hop on in, Jack,” Shelby said, waving at me towards her. “We are just relaxing a bit.”
The three of us were in the pool for around fifteen minutes, which was basically a get to know each other session. Like Shelby and I, James went to the same high school, and we trash-talked some teacher hard during our short conversation.
“Okay, enough small talk,” Shelby declared. “Why don’t we all head into the pool house for the fun we all came here for?”
We climbed out of the pool and toweled off as we walked to the pool house. Shelby walked into the pool house first and quickly spread a few towels onto the carpet. Then she took off and tossed to the side the coverup she was wearing.
“You sure you want to do this, James?” She asked her boyfriend for quick confirmation.
“I do,” he responded with no hesitation.
“Alright then,” she said and quickly removed her top, revealing her firm breasts and then her bikini bottoms, uncovering her shaven pussy.
James and I slid our trunks down as Shelby got onto all fours in the middle of the spread out towels. I knew my position, which was simply to get my dick blown, so I walked around to the front of Shelby. James got on his knees behind her; Then I dropped to my knees. His body was completely shaven because he was a swimmer and was fully hard already. Mine was at a semi-hard state, but I felt out of place and was nervous.
Wiggling her ass in the air, Shelby looked back and said, “Put a condom on and go ahead and do your thing, James.”
James grabbed a condom from the draw next to him, rolled it on and shoved his cock into Shelby’s pussy.
Her eyes closed as she felt the penetration from his hard shaft. “Ahhhh,” she muttered as her mouth fell open. When her eyes reopened, she was looking at my cock. Without saying a word, her tongue fished my hardening cock into her mouth. She concentrated on taking my shaft to its full hard-on state. Her tongue swirled, and she sloshed saliva all around my length.
James was busy rocking his cock in and out of her pussy when she looked up at me once I reached my full hardness. Shelby’s lips formed an airtight suction around my cock and moved rapidly across it.
“Fuck baby, you look so hot with his dick in your mouth,” James said as he gave her ass a soft spank.
“MMmmm,” Shelby responded with most of my cock in her mouth.
Shelby was pumping up and down my length when James asked, “She is pretty good at that, isn’t she?’
“Ohhh, yes, she is…” I responded as I helped move Shelby’s hair to one side.
For the next few minutes, James pounded into Shelby’s pussy as she worked my cock all over. She sucked, licked, swirled her tongue, and kissed all over my cock. Then James blurted, “Oh, Fuck,” and came. Shelby moaned and slowly withdrew my cock from her mouth as she experienced her body shaking from her own orgasm.
“Mmmm, yesss,” she exclaimed. “Hey, babe.”
“Yes, Shel,” James said as he caught his breath.
Grabbing my cock for the first time, Shelby held it to the side of her and said, “Looks like Victoria wasn’t lying.”
James gazed down at my cock, which was still at full mast. That felt weird, but that is the price of admission for a male-female-male threesome.
“What do you think?” Shelby asked. I didn’t know what she was referring to. “Would you be okay with it?” she added.
“If you want to, I’m okay with it,” James responded without hesitation or doubt in his voice.
Shelby turned back to me and looked up. “Obviously, Victoria and I talked before you got here,” she began. “She told me how big you are, which I told James.” She wiggled her butt into his softening cock when she said his name. “He is six and a half inches, so you are a tad over half an inch longer than him, and you are a little thicker than him, too.”
Shelby looked back at James, who had a straight face on as he was still recovering from his ejaculation. “Don’t worry, babe, like you are well aware…” she paused and looked down at his crotch, “you satisfy me plenty, and you’ll probably get lucky again tonight,” and she winked.
Then she ‘whispered’ to me, “I’m gonna marry that cock.” That made him smirk. I’m sure he didn’t need the reassurance but appreciated it.
Looking back up at me, she said, “James is the only man I’ve ever been with, and he wasn’t originally on board with the idea of another man fucking me like I told you earlier. I wasn’t sure myself, but the conversation with Victoria changed both our minds to allow it one time if you were willing.”
I didn’t respond right away, so she continued, “If you’d like to become my second, I made him wear a condom just in case I decided to ask you.”
I looked up at James, who nodded, giving me the okay to be Shelby’s second. My eyes darted to my crotch as I felt her tongue run down the length of my shaft. I enjoyed a few more licks before I stood up to move around behind her. James got up and handed Shelby the condom full of his cum, which she placed on her mouth and swallowed the cum. James laid down on his back in front of her with his legs spread wide open for Shelby to blow him.
“Cum inside her man… If that’s okay with you, babe,” James said.
“Mmm, it’s more than okay with me,” she responded as she bit her lip, looking straight into James’ eyes.
I got on my knees and lined my cock up with her entrance. As my head entered between her lips, Shelby thrust her ass backward and received the first few inches of my length into her.
“Ahhhhh yesss,” Shelby exclaimed. I pushed the rest of my cock inside moments after and held myself there. Her pussy convulsed against my cock. James fixed her hair and said, “Does it feel good, babe?”
“Mmmm,” Shelby responded and started to suck on James’ balls.
I began to work my cock in and out of her tight pussy. I started slow but was only building up to a good hard fuck. Meanwhile, Shelby was slurping up and down on James’ cock like it was going out of style. My hands were on her hips, helping stabilize her – she liked to wiggle around from sucking on cock and having one deep inside her.
I could tell she was tense by how her hips reacted to my thrusts inward, let alone her pussy squeezing my cock. When I was ready to really start pounding her, I leaned down, grabbed her right breast, and squeezed.
“Do you want me to go a little faster?” I asked.
“Mmmm hmmm,” she responded, taking James’ cock out of her mouth for the first time in minutes.
Taking a firm grip of her hips and repositioning my knees, I pushed in and withdrew slowly one more time before thrusting hard inward. Shelby moaned, and that’s all the reaction I needed to begin to thrust harder. I wasn’t pounding her as hard as I could, but I was giving her a good fucking as she sucked off James.
What Victoria and I had done was make love and, to this point, had never truly ‘fucked’ a woman before, but the vibe Shelby and James gave off was different than what I had ever experienced. They didn’t want me to make love to her pussy, nor have sex, but instead, they wanted me to fuck her.
James propped himself by his shoulders before gazing down at his girlfriend, whose eyes were shut tight as she sucked his cock. Then he gazed up at me and said, “Fuck her good, Jack. Fuck her good,” and he collapsed back down.
My cock was nearly fully withdrawn, with each pull backward before I slammed back into her. Her butt jiggled as It absorbed my thrusts from the mating of skin. Shelby’s mouth never left James’ cock, but she moaned and purred the entire time. Shelby then began to lower her chest and torso, leaving her ass in the air.
I was lost in pounding her as she lowered herself that I had forgotten James was at the other end. He grunted and proclaimed his orgasm bringing me back. Shelby was swallowing every drop of her boyfriend's cum when her right hand moved to her clit, and she began to rub it.
Shelby popped James’ cock out of her mouth and said shrieked before saying, “I’m gonna cum, Jack, yessss!”
Her body shook as she was still rubbing her clit. I was pulling her hips into my thrusts. Meanwhile, James had gotten onto his knees and was kneading her breasts.
I was approaching my own orgasm, but I was biting my lip and couldn’t speak. Shelby sensed this and announced, “He is gonna cum baby.”
“Jack, dump your load into her pussy,” James said. Not how I would have worded it, but whatever.
My last few thrusts into her pussy were very hard and accompanied by sensual squeezes from her.
“Fuckkkk,” I said in a low grunt as I started to cum.
“Mmm yessss, Jack,” Shelby yelled as her fingers still rubbed her clit, and her head fell. James was smiling as he watched me cum in his girlfriend, and she had a second orgasm.
Three more thrusts and a pull on her hips and Shelby’s pussy was full of my cum. We both wiggled our hips as I held myself within her. James’ mouth was agape as he continued to knead her breasts. His crotch was right in front of her, and she kissed his soft cock.
“Thank you, James,” Shelby whispered. “I know that was more than we had planned, but wow it was an amazing experience to share with you.”
“You are welcome, baby. It was wonderful to watch you enjoy it, and I enjoyed it, too,” James replied.
They were having a moment as a couple and exchanging ‘I love yous,’ all the while my cock, albeit softening, was still inside her.
I finally withdrew my cock from her pussy. Shelby spun around and gave my softened shaft a quick kiss, then sat up and pecked my cheek.
“Thank you, Jack,” she began. “I know that was more than what we had discussed earlier, but I think you enjoyed it. I know I did.” She was beaming with a smile.
“Was it that obvious I enjoyed it?” I said sarcastically. “I’m happy you trusted me enough to help you and James explore a bit.”
“I can’t speak for James, but I don’t know if I’ll ever want to do it again, but now I can at least say I’ve done it.” She reached around without even looking and instinctively grabbed James’ cock and balls. “This cock is plenty for me and makes me a very happy lady. I cum every time.”
Again, James didn’t seem like he needed any reassuring that Shelby was his and in love with him, but I could tell he enjoyed her sharing that.
Shelby leaned closer to me, “He is gonna get lucky again tonight. Probably in his parents’ bed,” she giggled.
James finally spoke and thanked me for helping them and giving Shelby a good time. The three of us then exited the pool house and into the main house buck naked. Shelby was leading us, and both James and I admired her.
“Shelby is more than a great body, but damnnn, she has a great body,” James said to me.
I nodded in agreement.
“I heard that,” Shelby said and purposely swayed her hips more.
In the bathroom, I put my clothes back on. I didn’t even bother closing the door behind me as Shelby and James went into the master bathroom and heard bath water start to fall. I was just exiting the bathroom where I changed when Shelby came up to me, still naked, “I’ll show you to the door.”
“Thanks again for agreeing to this, Jack,” she said.
“It was my pleasure,” I said. “It was different, but it was fun, too.”
“Well, like I said, James and I are just wanting to try different things and explore new sexual experiences, and I hope you don’t think we used you. Even though we kinda did.”
“Not at all,” I replied with a smile.
She hugged me and kissed my cheek once more before opening the door and standing to the side so any neighbors out and about wouldn’t see her.
“See you at work,” I said as I walked down the path.
“Yep, try not to act all weird when you see me,” she laughed.
“Oh, you know I will,” I said with a smile and sarcasm.
“Bye, Jack and thanks again,” she said, laughing, and shut the door.
Things didn’t change between Shelby and me at work at all. In fact, most of the time, it was like what happened that evening never did happen. She could be more playful and flirty with me occasionally, but it came from a good place. I would never have any more sexual interactions with Shelby. But that one time is one I’ll always remember.
I left the store to go to grad school two months later, but I saw her that December. Shelby shared that with me that I was still the only other cock to be in her pussy other than James, and she didn’t see that changing anytime soon.
“What about your mouth,” I chuckled.
She smirked and lightly punched my arm. “Well, you were the third cock in my mouth,” she said as she blushed. “And for your ears only, I have had a fourth. James knows, but I don’t see a fifth happening. This experimenting has really made us appreciate each other a lot, and you played a part in that.”
We smiled, exchanged goodbyes, and I left to go check out my groceries. I’ve seen Shelby and James a few times since. We simply smile at one another as we discuss other things.
