Tom was lounging on his couch at his apartment when she messaged him.
what are you up to
He had seen her story posts earlier in the day and knew she had been day drinking at some vineyards with her girlfriends. He thought back to the last time they had messaged while she was out drinking with her friends and a smile crept across his face. The conversation had turned raunchy rather quickly when she had explained one of the girls she was out with had never received a dick pic. Needless to say that went down a road of sexting, her sneaking off to the bathroom once or twice to take titty pic, and eventually requesting he cum for her and send proof. Right before he was about to cum she let him in on a little secret that the girls she was out with had been helping her sext him the entire time. Tom, while seemingly shy, was a closet exhibitionist and loved to show himself off. This little tidbit that they had been in on the sexting and looking at his dick pics as he sent them (plus, were waiting to see him cum too) was such a turn on for Tom. That sent him over the edge that night and he came so hard he felt like he almost passed out. He loved putting on a show for her and her friends. Once she was alone, she later let him know how hot she thought the video of him finishing was.
Tom lazily pulled his cock and began stroking it in hopes this was another similar situation. Tom texted her back he was having a night in and asked what she was up. She replied back that she was back at the Airbnb and the conversation amongst her friends had turned to sex toys. One of the girls divulged the guy she had recently been on a date with had left some sort of mechanical stroker toy out in his sink on accident.
I want to show them that silicon torso toy you have
Tom sprang from the couch, went into his room, and removed the toy she was describing from a box under his bed. It weighed maybe 20 pounds and was basically a torso with a pussy opening, an ass opening, and some huge squishy tits. Tom remembered the escapade they had when he unboxed it. They eventually wound up virtually fucking each other over video chat as she rode a suction mounted dildo and he simulated her movements by holding the torso toy by its hips and riding himself with it. He came so hard as they dirty talked and reminisced when they had fucked each other over and over in that hotel room all those years back. The toy felt great but was nothing when he thought back to how good her pussy felt.
He laid the toy down on his bed so its ass was prominently displayed and its tits were pressed against his sheets and spilling out to either side. He snapped a photo and hit send.
He was so horny already from this brief exchange. Her texts always seemed to get him worked up almost immediately. He stripped down to nothing, poured a healthy amount of lube into the toy's asshole, and slowly shoved his hard cock inside. He secretly hoped this would turn into some more sexting.
[Nikki video call incoming]
Oh shit. He hadn't expected that in the slightest. Tom declined the call and messaged her that he needed to get dressed really quick and to give him a second.
No. Keep doing what I know you're doing and answer the video call
He felt himself almost cum at the thought of what she was requesting. The call came in again and he answered. He stopped fucking the toy and made sure the self-facing camera was only framed on his face before he answered.
Nikki as well as all her friends filled the screen. Tom felt his face redden slightly and slowly pushed his cock all the way in until the silicone cheeks were pressed against his hips. The toy gripped him tight as his cock flexed in anticipation. A brunette who he had seen photos of before with Nikki cooed into the camera, "Hi Tommy, we wanted to see what you were up to."
Another blonde he also recognized giggled and called out, "Flip that camera around big boy and entertain us with that dick."
Nikki leaned in close to the camera and whispered, "Show us Tommy. I know you like being watched."
Tom slowly began to fuck the toy which was making very audible squelches as he slid in and out of it. He kept the camera facing his face as he nonchalantly asked "How's the day been ladies?" His torso obviously moving just out of view in thrusting motions coupled with the unmistakable sounds of his cock sliding in and out of the toy.
A second brunette spoke up, "Fuck this is hot. Stop being a tease and show us that big cock, Tom. We want to see. Nikki showed us that pic of you with a ruler. I wanna see if you're really that girthy."
Tom flipped the camera around and slowly panned down as he continued to work his cock in and out of the doll's ass. The opening wrapped tightly around his shaft which was glistening with lube.
"Ooo you bad boy. How much do you want to cum right now?"
Tom had to stop thrusting and take a deep breath to stop himself from exploding at that question.
Multiple giggles as various girls chimed into urging him not to cum yet.
Nikki's face filled the camera and announced a challenge. "If you last another 5 minutes, one of us will fuck a dildo for you"
Tom loved challenges and told them it was a deal. No sooner had he agreed than Nikki and her friends immediately took their tops off and began laughing.
