JS Sidestory - Jessica & 3 New Friends

Just a week earlier, she experienced her first happy-ending massage; it was amazing! With her husband Steve's enthusiastic permission, she had arranged to meet the massage guy at a hotel this evening for a second go-round. She was sure there was going to be a lot more than just fingers involved this time.

She got to the hotel bar early to have a few drinks to calm her nerves. By the time he was supposed to be there, she was feeling no pain. A sharp guy in a business suit had struck up a conversation that killed time while she was waiting. The massage guy texted to say he was caught behind an accident in traffic and would be running very late. Her new friend, named Gates, bought her another drink. Their conversation grew intimate. As she was drunk, she confided in him why she was there. Which quickly got his full attention. Maybe it was the booze talking, but she told Gates she had a very open marriage, where they encouraged each other to fulfill all of their desires. One of her husband's fantasies was that she hooked up with a complete stranger and tell him nothing about it until the next day.

Gates smiled and offered to fulfill that fantasy. She laughed it off as if they both were kidding. She was already meeting a guy to have sex with, and that was plenty for the night.

With so many drinks in them, eventually, they both had to go to the bathroom. So they walked together. She could feel his eyes on her body, and his offer washed around her mind. They went to their separate bathrooms.

The women's bathroom was immaculate because no women were in the bar. She finished her business, and as she washed up, she thought more about what he offered. She imagined it, and it got her hot. So hot that she needed to do something about it. There was a chair in the bathroom where she sat back, lifted her skirt, and began to masturbate herself to the fantasy of having sex with this stranger. Her pace increased as she lay back in the chair with her eyes closed and fucked her pussy hard, bringing herself to a powerful orgasm.

She opened her eyes and was stunned to see Gates standing there. He was handsome, a bit pale, very well dressed with a nice body in his tailor-made suit. She also could tell by the bulge in his pants that he was well endowed and had enjoyed the show. He walked up to her, and without hesitating, she reached out, unzipped his pants, and withdrew his enormous hard cock. She was surprised at how large it was. He pressed it to her face, and she willingly opened her mouth to allow it in. Gently at first, with his hand on her head, he started to fuck her mouth. She rubbed his balls and pulled on his cock with one hand, and massaged his firm ass with the other. She wished she had her camera handy, knowing how this scene would turn Steve on.

He lifted her by the hand and placed her facing the counter. He moved behind her, and she felt his tongue on her snatch and his fingers probing her ass. He licked with long strokes between each hole, allowing him to sink his tongue in each. With his tongue in her ass, she came for the first time.

He paused and looked at her, "would your husband like seeing this?"

"Oh dear lord, yes!"

"Do you have a camera?"

She retrieved the tripod and her cell and set it up. They forgot about it as he went back to licking her ass.

He whispered, "Do you like having your ass licked?"

"Yes"

He moved for a moment to her ear, "then tell me how good everything I do is." And he went back down between her legs. "What do you want me to do?" He asked.

"Lick my ass, please, Gates, you are so fucking good!"

He liked her talking. He stuck his tongue in her ass.

"Oh yes! Lick my ass!"

He buried three fingers in her pussy and fucked her with them while his tongue continued to dance.

"Oh fuck, you're going to make me cum!"

He fucked harder until she exploded, "oh my god, I'm cumming. I'm cumming so fucking hard!"

She collapsed on the counter.

He rose quickly and, without hesitation, buried his dick in her pussy. It was huge and felt so good she instantly came again. "Your cock feels so good!"

He continued to pound, and she continued to cum.

She wanted something else. "Gates, please fuck my ass! I need you to fuck my ass!"

He gladly obliged and slowly worked his enormous cock into her ass. It took several painful seconds, but eventually, her ass was filled completely. "Fuck me!" She begged.

At first, he was slow, but eventually, he slammed his full body weight into her ass. She was racked with orgasms. Finally, she could feel him swell inside her. "Gates, cum in my ass! Fuck it hard and cum in my ass! I want you so bad!"

He responded by pumping her full of so much cum it poured out after he removed his cock.

He turned off the camera and kissed her neck passionately before she asked him to leave so she could freshen up. She turned the camera back on and turned her cum filled butt to the camera. "Is this what you wanted, honey?" Knowing it's precisely what he wanted and more. Who knew making her husband happy could be so simple.

She came out of the bathroom, reentered the bar, and to her surprise, the massage guy was the first person she saw. He looked relieved. "There you are. I was afraid you'd left. Ready for your massage?"

They left the bar together without acknowledging Gates, except just as she passed him, she said far too loudly, "I am staying in room 227."

They entered the room, and she set up the camera after getting his consent. It started where they had left off in the last massage; Jessica naked on the bed. The massage followed the same sensual path. He massaged her ass, his fingers slipping further between her legs, eventually stroking her pussy. She did not fight his touch; she opened her legs further. He massaged her pussy for it seemed 30 minutes until she was utterly soaking set and on the brink of her first orgasm with him. He mentioned how wet she already was, and with a bit of a guilty conscience told him she was thinking about him most of the day, which was technically true.

He sunk a few fingers inside her, and she moaned and pushed back against him. He finger fucked her until she came all over him and loudly. He didn't pause but continued to work her pussy harder. She reached back and spread her cheeks as a signal. He picked up on it and slid fingers in her ass as well, fucking both holes to another orgasm.

He removed his clothes and moved around in front of her to massage her shoulders. His dick was bobbing in front of her face. She pulled him towards her waiting mouth. He rubbed her back and fucked her mouth, pressing to her throat. Then he slipped around behind her up on the bed. She felt his stiff cock enter her pussy, and she came immediately. He started slowly but picked up force as he started fucking her vigorously.

The sound of his body smacking up against her was so loud that neither heard the door opening and closing. Fucking her passionately, he was laser-focused on her moans and orgasms. He stopped sharply when to his surprise, a strange man had hoped on the bed in front of her.

They were all frozen in confusion until Jen made a move. She took Gates's cock and put it between her lips. Confused but still deep in her pussy he fucked her even harder. Until he came deep inside her. He moved aside and watched Gates roll her over and climb on top of her. Gates slammed into her, and they both fell into huge orgasms.

Exhausted, they sat back and talked about how they came to be here. As she spoke, she stroked both of their dicks until they were both hard again. She went back and forth, sucking both of them. Then on her back Gates was in her pussy again while she sucked Mr. massage. Gates rolled her over on top of himself, and the other came around to where her pussy was filled with cock. He shoved his cock in her ass as Gates whispered in her ear a reminder from before.

"Oh fuck, this feels so good with your cocks inside me. Your cocks feel incredible! Oh, your fucking me so good!" Then she called out their names each time she came and begged them to keep fucking her, which they did.

Finally, after a 1/2 an hour, they were getting close to cumming, and she wanted it bad. "Cum in me!"

Gates asked, "are you a cumslut?"

"I am a slut. Please fill me with your cum! I want you so bad to cum in me!"

This was too much, and simultaneously they both shot loads deep inside her. She felt so good and full that she simply closed her eyes and fell asleep.

The next morning she was surprised to wake up in the hotel room and feel a hand rubbing her pussy. She kissed him as she turned to him and grabbed his cock. Fingers probed every inch of her. Then she felt the kisses on her neck and another set of hands; they had both stayed the night. Gates had her talk nonstop about how much she loved their cocks, what they were doing to her, and how bad she wanted them to fuck her.

She rolled on top of Gates's dick in the morning light and looked down at him. He was quite handsome in a John Mayer sort of way. She kissed him passionately as she ground her pussy down on his cock. Meanwhile, her other friend had moved behind her and quickly joined them for a DP treatment again. Gates held her hair and made her talk about how much she loved it. It was the best she'd ever have, and how she wanted them to fuck her forever. She knew the camera was off or out of power, so she just said whatever came to mind. "Fuck me hard! God, your cocks feel so good! Use me like your little cum slut!"

She was lost in the pleasure of ramming both hard with unbound lust when the maid, finding the door partially opened and assuming it was a room to be cleaned, walked in. Everyone froze. "Lo siento, I am sorry." She said as she began to back out of the room. The room was a little wonky, so Jessica broke the tension, "Too bad she had to leave; she was hot! I would have loved to eat that pussy." They heard the door click shut. This drove the boys wild, increasing their force until their entire bodies were pounding with maximum power. Jessica had lost track of the total number of orgasms, but finally, she came uncontrollably with a squirting orgasm that enveloped her whole body. The boys went over the edge and filled her to the brim with their cum. Exhausted, they uncoupled. Gates had to catch a plane, and the other had an appointment. They exchanged niceties but no information with Gates and only a vague suggestion of possibly seeing her masseuse again. They left.

She was tired and wanted to sleep, but with check out only an hour or so away, she didn't want to go home dripping cum, so she jumped in the shower. She cleaned herself thoroughly, and with memories of the night fresh in her head, she masturbated to a furious orgasm.

She dried herself off and walked back into the room. To her surprise, the hot maid was on the bed with her uniform on, except her pants and panties were off. She looked right at Jessica, "You said you would love to eat my pussy." She spread her legs and touched herself seductively. Jessica crawled into the bed and went down on the maid for an hour straight. She expertly used her finger to fuck the maid in her ass and cunt and make her cum over and over. She was too sore, so she just served the maid. Finally, the maid had her last massive gushing orgasm and held Jessica's face in place to take all of it.

She recovered after a few minutes and apologized to Jessica, saying she'd never done that before. She and Jessica exchanged contact information. She was 100% lesbian and was okay with Jessica being married. She mentioned that a bunch of her friends would love a girl toy they could use without worrying about relationships. She kissed Jessica passionately, then dressed and left the room.

Jessica packed up and, retrieving her phone, realized that at some point in the night, it had been plugged in, and the camera was running all that morning as well as capturing the evening's festivities. She watched a bit of the video and thought, "Steve is going to be well pleased." He was!