Summer Surprise Pt. 05

"I'll talk to you later. Thanks."

"Goodbye, Yolanda. Give him hell," Chloe said.

******

"Well, boys and girls, are you as excited as I am?" Chloe asked, the door to the apartment locked.

"More nervous," Matt said, "but willing to give it a try."

"Why don't you go into the bathroom and remove your plugs and take a shower. Let's approach this all nice and clean. I'll get everything else we need after my shower."

They nodded and went into Dianne's bedroom. Matt was fairly silent while the showered, preoccupied.

"Chloe is right you know," Dianne said.

"About what?"

"We'll stop if it hurts and won't do it anymore if you're uncomfortable with what happens."

"What if I like it?"

"I'm not sure I understand the question?"

"What if I like getting fucked in the ass?"

"Then you like it. So what?"

"Would it mean I'm gay?"

"Is that what you're worried about? You'd be gay if you liked it?"

"Yes."

"You're one of the least gay guys I've ever met. So if Chloe likes getting fucked in the ass by a cock, she's a heterosexual? Or if I like getting pegged with Chloe's strap-on, I'm a lesbian? I don't think one thing has anything to do with the other. Just because it's one of the ways gay guys enjoy sex together doesn't mean it's only for gay guys. Lots of non-gay people enjoy anal sex. It's like saying sucking cocks makes me a gay guy since I enjoy sucking cocks because that's how gays enjoy sex. You'll either like it or you won't based totally on it's own merits.

"I doubt you'd be running around campus tomorrow looking for cocks to suck if you enjoy anal sex tonight. It doesn't work that way. You should be worried about my tender young ass. You're going to be putting this big dick inside of me popping my anal cherry." She fondled his cock, feeling it grow in her soapy hands. "I'm the one who should be concerned. You've got nearly an inch less to worry about."

Matt laughed. "I suppose you're right."

"Damn right I'm right. You're going to be fucking two women tonight, one of whom is a dedicated lesbian. I can't think of anything less gay than that. Just relax and see if you enjoy it. Nothing else matters."

Chloe was already in the bed naked when they finished up. There were two more large plugs, lube, a strap-on, a purple, double headed dildo, and a towel on the bedside table.

"I didn't think I was getting plugged again after today," Matt said.

"You're not. That's for me. You will eventually fuck my ass and I'm not used to anything as large as your pecker in my pucker either."

"So, you're the ass fucking expert. What do we do here?"

"You look tight as a drum, so why don't you lie face down on the bed and let two beautiful naked chicks give you a back rub. Just close your eyes and relax."

Matt got on the bed, closed his eyes and in short order, Matt felt two sets of hands rubbing his back and legs. He'd shown them often enough how to give massages, so they were doing a good job and he felt himself relaxing. At some point, one set of hands left his legs. A few minutes later, they returned. Then he felt a pair of lips on his bottom, kissing it. That didn't bother him at all. He heard whispering and the hands on his back slid down over his ass and parted his cheeks. He tightened up a little, thinking it was about to happen, but instead he felt a tongue slithering through his crack. He found his buns relaxing again under the gentle licks of the tongue. Matt even felt it probing lightly at his back door, and felt himself relax more.

Then someone, he didn't open his eyes to find out, was rubbing lube over the crinkle. It felt good, not invasive at all, more like the massage, just a different place. Dianne leaned down and kissed and nipped his earlobes. "Spread your legs more, lover."

Matt spread them and felt Chloe get between them. She continued rubbing his back, but now he felt the tip of something else poking at his pucker, exerting pressure, but not a lot. He tightened initially, but when it didn't try to force itself past the rim, he relaxed again. As he relaxed, he felt his crinkled star part under the pressure. He took a deep breath and forced himself to relax further and felt the bulbous head pop through to the shaft. It was smaller than the last plug, but he knew it would go much deeper. He did feel himself become erect. It definitely felt good enough to get him started.

They kept rubbing his back and more and more of the faux cock slid into the lubed entrance of his backside. Chloe was going slow, very slow, and it didn't hurt at all; felt pretty good if he was being honest. Better than Matt expected. Definitely a sense of fullness. Finally, it was ended and he could feel hips against his buttocks.

"I'm all the way in, Matt. How do you feel?" Dianne's voice?

Matt opened his eyes and saw Chloe kneeling in front of him.

"I thought you were going to do my ass fucking," Matt said, cognizant he was still damn full in the back.

"Yeah, I thought if you were going to take Dianne's anal cherry, she should take yours. It's only fair. The reason I was going to do it is because this next part, Dianne would be so much better at than me, since I haven't sucked cock in years, but what the hell. She's going to be doing most of the work encouraging your orgasm. I'm just the receptacle. You need to get on your hands and knees slowly so Dianne doesn't slip out of you, and get ready for a little tongue action on your knob, because I won't be able to get that whole thing inside my mouth to save my soul."

Matt slowly got on his hands and knees, Dianne moving with him so they'd stay connected by the rubbery protrusion jutting from her groin.

When Matt was ready, Chloe said, "Nice and slow, Dianne, start fucking him. Let Matt get used to it before you start banging away on him like he does you. I'm going to be busy and unable to talk."

Chloe got beneath Matt and wrapped her lips around the tip of his prick. The strange thing was, as he started thrusting back and forth in Chloe's mouth, he was also fucking himself on the strap-on. And it started to feel good, really good. It was odd having something up his bum, but he'd spent the last three days with something up there. This wasn't much different. And Chloe may not be the cock sucker Dianne was, but having her tongue laving the head of his prick was heavenly.

As Matt increased his the speed of his thrusting in Chloe's mouth, so too did the speed of the thrusting in his buns increase. Dianne was taking good long strokes into his backside. About ten minutes in, Matt felt the sperm in his balls starting to boil and knew it wouldn't be long. He imagined he should give Chloe fair warning.

"Chloe, it won't be much longer. Just saying."

She tapped his leg and kept up her oral action. It felt great, better than great. Matt felt like he was going to explode. He had warned her. One final deep thrust by Dianne and he felt the dam burst, his cum making the short journey from his sack to Chloe's mouth. Matt groaned deep in his gut as the cum spewed out like a fire hose. Chloe kept sucking right through his orgasm until he was shooting blanks, his cock still twitching but nothing coming out.

"Oh, fuck!" Matt groaned. "I hate to say this but you need to stop sucking. It's too sensitive."

He could feel Chloe giggle before she pulled off him with a sodden pop.

"Ewww, man juice. Pussy cum tastes much better," Chloe said, pulling out from under him. "So, Matt, how was your first ass fucking?"

"Pretty damn good. I could see doing it again."

"When I fuck your ass, I think I'll do it while you're fucking Dianne. It will almost seem like fucking Dianne with your cock. Dianne, you might want to use that towel to wipe down the strap-on, then take it off and I'll wash it. We'll do our thing as soon as I'm done with cleaning chores. We'll put each other's new plug in when we're done tribbing."

Dianne used the towel to wipe the strap-on off, removed it and Chloe took it from her, going into her bathroom to wash it. She returned.

"Why not use our bathroom?" Dianne asked.

"I have a special toy cleaner. I use soap and water, then the cleaner. I suppose I could leave the cleaner in yours. Are you ready Dianne. Are you wet? No, don't tell me, let me see for myself."

Chloe wrapped her arms around Dianne from the back, sliding her hands from the taut nipples, over the flat stomach and down to the furrows hidden in the trimmed pubic hair. A finger deftly slid through her slit from her clit to sheath, testing the dampness while kissing her neck.

"You're slicker than I thought you'd be. Nice. You must have loved shoving your fake dick into Matt's ass. I don't think we'll need lube to get us started at all. Matt, don't think you get to lie there like a lump and watch us. You need to lick breasts and kiss us, a little here, a little there."

Chloe got on the bed, sitting, but leaning back on her arms and said, "Interlock your legs with mine and slide into me until our cunts are together. I'll get a nice motion going. After we both cum, we'll add the dildo."

Dianne did as she asked until her folds were mashed against Chloe's. Chloe started grinding her hips, causing their pussies to slide against each other. It felt good. As Chloe said, both of them were already leaking slightly and the slickness allowed them to slip easily against their partner, rubbing their vulvas together in a strange dance. It felt even better when Matt softly kissed Dianne's neck, her shoulders and eventually her breasts, suckling on the nipples. Dianne moaned.

"Feels good, doesn't it," Chloe panted.

"Yes," Dianne whimpered. "Great."

Dianne found the rhythm Chloe was using and ground against her in counterpoint. It made it easier when Matt left her and kissed and caressed Chloe the same. When she was distracted, Dianne could grind.

A few minutes later, Matt was caressing her again. "I'm close, Chloe. Don't stop. It feels so good."

"No fucking way I'm stopping," Chloe said. "Cum for me, baby."

"Oh, oh, oh, ooohhhhh, shit! I'm cumming."

Chloe could feel the tremors of Dianne's spasming pussy against her own, the increased flow of fluids making it even easier to slide against her. She increased the speed and pressure of her rubbing, getting herself off from the stimulus of their pussies smashing together. Matt moved over and suckled her breasts which spun Chloe's orgasm up another level.

"Uh, uh, sweet fucking Jesus, that feels good, Dianne," Chloe panted, cunts mashed together, trembling through some pleasant aftershocks.

Chloe opened her eyes. Dianne's were still closed, her body still shaking from the intensity of her orgasm. Matt had another erection. He was nibbling on Dianne again.

"Matt, I don't want to move much. This feels too good. Can you grab the dildo and the lube? And how the hell do you have another boner? You just climaxed like twenty minutes ago for Christ's sake. I felt like a swallowed a pint of cum."

"That was pretty fucking hot," Matt said. "No wonder Marty has a lesbian fetish. That was awesome. Wait one. Are you sure you need the lube? Your pussies are soaking wet."

Chloe reached down and felt both hers and Dianne's groins. Dianne shuddered again. "Skip the lube, we're good. You get the pleasant task of inserting that baby in our cunts, starting with your girlfriend, then line it up for me and we'll go again. You just keep doing what you were doing. That felt perfect."

Matt got the double headed dildo off the nightstand and after Chloe pulled back from Dianne, inserted one end into his girlfriend. Matt had no difficulty inserting it, Dianne was plenty lubricated. It was thick, smaller than Matt, but hefty enough, Dianne orgasmed again when he was putting it in her. Dianne had her arms around Matt's neck, dragging his head down for a kiss as she trembled through this orgasm.

"It feels so good, Matt," she whimpered. "Everything feels so good."

"I'm glad you're enjoying it."

She continued to shake as Matt got half of it in her. Chloe slid across the sheets until she was close. When Matt had the other end aligned with Chloe's pussy, she pushed over the head as easily as Dianne had done. When their pussies came together, it was with a sodden squelch. Chloe gave it half a minute before she started the thrusting/grinding she'd done before. Matt continued playing with the two women, sucking a nipple on one side while caressing a breast on the other, then switching. Over the next fifteen to twenty minutes, both women enjoyed several more orgasms.

They finally had to stop due to sensitivity, every continuing touch like a spark of electricity. When Matt helped remove the dildo, it was coated with the fluids from their orgasms, white cream forming a line where the two women had been joined on the purple dildo.

"Taste both ends and tell us which pussy juice you like more?" Chloe said, leaning back on her arms, still closely proximate to Dianne, who was collapsed on her back, one leg bent, the other sprawled.

"That sounds like a recipe for disaster, telling you both whose pussy tastes better."

"Wise man, Sanders," Dianne said. "My pussy better always taste the best to you, regardless of whether it is or not, but taste them anyway."

He licked and sucked the top inch or two on both ends. There might be subtle differences in the taste, but both sides made his dick tighten with arousal.

"Dianne," Chloe asked, "do you have enough energy to do one more thing?"

"Depends on what it is?"

"Open your eyes and look at your boyfriend's cock."

Dianne opened her eyes. Matt's dick was sticking up from his groin like a flagpole, stiff as a poker, skin tight and shading towards purple on the head.

"Does he look close to popping to you?"

"Yes. Wouldn't take much to my way of thinking."

"My thinking is us rubbing our cunts together with his cock in between them until he squirts. What are your thoughts on the matter."

"I'm game to try. Could be fun."

"Matt, lie on the bed. Dianne, you take the left side, I'll take the right. Crouch down, ass facing me, over his hips and meet in the middle."

"Got it."

Matt quickly lay down in the middle of the bed and the two women aimed their asses towards each other and backed up. He held his cock up straight and they suddenly met against his prick, their soft, slick folds mushing around the head of his cock; wet and hot. They began sliding their slits up and down his cock from the plum shaped head halfway down. As Chloe suggested, Matt was ready to explode. It only required five minutes of their delightful pressure against his throbbing shaft before his cum bubbled up out of his prick and ran over the glistening folds of Chloe and Dianne, Matt groaning the whole time he pulsed his load.

"That's a bit of a mess," Chloe said as the thick cream started dripping down to Matt's groin.

"At least it's still fresh, and not dried," Dianne said, turning around to lap at the puddle formed at the base of his stalk.

"Aren't you going to help, Chloe?"

"I've already had a mouthful of man juice. Too much might be bad for my pussy juice complexion."

Dianne laughed. "Have it your way." She finished with her housekeeping chores. "Well, that was a pleasant experience, but I'm exhausted. We definitely need to retire."

Chloe got up to wash the toys, then returned. "On your hands and knees, Dianne, ass up, head down. I've decided to jump up a size and skip the next one since you've not had a problem thus far. We're both going for what we need for Matt's thick prick. Tomorrow night, you can feel Matt plugging your backside."

Dianne smiled and got in the required position. Chloe did use lubricant this time. She smeared it liberally around Dianne's rear entry, including slipping a couple fingers in to stretch the rubbery muscle, and a lot on the large plug.

"This may hurt a bit more getting in because it's a full half inch larger, so relax and let me do my thing. It's good you had some nice orgasms first."

Dianne was stoic until the plug was close to its widest point, then she groaned. "Is it much more? Please tell me it's almost in."

"Almost," Chloe said. "Hang in there a couple more seconds."

As soon as it was past the thick part, it was almost sucked in as the muscular rim closed around it.

"Oh my! That's substantially thicker isn't it?" Dianne remained in that position, almost afraid to move.

"A half inch more is nothing to sneeze at," Chloe agreed.

"I don't want to move. Any chance Matt can put yours in?"

"I might even enjoy it since Chloe is the one who suggested I get fucked in the ass," Matt said. "Assume the position, Hamilton."

Chloe got up beside Dianne and Matt got the lube and put some on Chloe. He'd watched her doing Dianne, and did pretty much the same thing, except his fingers were larger. Chloe told him to use two as it had been awhile. So he added more lube and inserted a second finger, twisting them back and forth. Matt added a lot of lube to the plug and placing it Chloe's pucker, started to push.

Chloe was grunting the deeper it went.

"What I think is kind of funny is you're going to be up on stage tomorrow afternoon with this plug in your ass. I wonder how that will affect your performance."

Chloe started laughing which had a tendency to push the plug out. Dianne was laughing with her.

"You just had to say it, didn't you, you sister fucker. Balls, it felt like it was almost in, too."

Matt chuckled. "I think it was. You want to try relaxing again so I can push it in?"

Chloe relaxed her buttocks as much as she could and Matt pushed it through the barrier until it seated itself in her lovely derrière.

"It's almost like staring at a couple of bullseye targets," Matt said, "asking me to spank here."

"Don't you dare," Dianne said. "I already feel kinky enough with this thing in my ass without you talking about spanking me."

"Really, you haven't tried a little erotic spanking yet? That gives me some wonderful ideas," Chloe said. "We have the whole evening tomorrow since it's a matinee performance."

"Let me get through the ass fucking first, before you start adding more of your kinks."

"Since you're both kneeling there so prettily, and right next to each other to boot, I want to finger both of you, if there's no objection."

They looked at each other than put their heads down on the bed. "What the hell," Dianne said, "what's another orgasm or two between friends."

"Wait here. Let me wash my hands first since I was playing around with Chloe's ass."

Matt jumped up, gave his hands a good wash and returned. They were still in the same position. He slipped the two middle fingers of each hand into the slippery sheathes and fingered both of them while using his thumb to slide over their clits. Within a couple minutes both of them were moaning delightfully. Dianne climaxed first as Matt was using his dominant hand on her, Chloe following shortly afterward. He gave them each one more, before pulling them out and licking his fingers clean.

"I can safely say, you both taste pretty damn good," Matt said, "and vive la difference."

Dianne took the middle again, curled around Chloe, while Matt got behind her.

"Don't tell me you're erect again, Matt. For God's sake," Dianne said. "Go to sleep."

"I will, don't push back against me though, or you might end up with a bit of a surprise guest."

Dianne pushed back against him and felt his cock at the entry to her pussy.

"Don't fuck me, but push in a couple inches, so I can see how full I feel."

"If I push in a couple inches, I can't guarantee no fucking. He'll have a mind of his own at that point."

"Push in anyway."

"If you can fuck her without disturbing me," Chloe said, "more power to you."

Matt pushed in a couple inches and he tried to hold still, but apparently, Dianne liked it too as she eventually moved to accommodate Matt's entry and he ended up fucking her to another orgasm. His cock was still buried inside her when he fell asleep.