Mar 30

Couples Weekend at the Resort

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Double Penetration

Anna and Dave had been married for about 7 years. Anna’s best friend, Wendy, had been dating Matt for about two years. Matt was a good guy, very handsome and kept in good shape. Anna thought he and Wendy would get married eventually, but Wendy wasn’t so sure. The four friends decided to go on a joint holiday over a three-day weekend. They all took off the Friday before and booked two adjoining rooms at a resort a few hours’ drive from where they lived.

About two weeks before the trip, Wendy called Anna in tears. She had come home early that day and found Matt in bed with someone else. She caught Matt wearing leather chaps and a ball gag, bent over a chair while her personal trainer, Kyle, pounded him from behind. Wendy could tell this wasn’t their first time.

They broke up and Matt was moving out. Wendy wanted to cancel the trip, but Anna convinced her to go. “We’ll have fun together, the three of us. Besides, it’s too late to cancel, you might as well enjoy the weekend.” Wendy reluctantly agreed.

Anna called ahead to let the resort know that Wendy would be coming alone. She didn’t want a bellhop asking Wendy about her boyfriend and ruining the weekend.

On the Friday morning of the long weekend, Anna and Dave picked up Wendy at her place. Anna had worked late the night before, so she let Wendy ride shotgun and caught up on her sleep in the backseat. Dave and Wendy had never really talked to each other alone before, but they found they had quite a bit in common. Dave was a funny and genuine guy. Wendy found it a breath of fresh air after two years of dealing with Matt. By the time they reached the resort, they were laughing and carrying on like a happy couple.

After they pulled up, Dave grabbed his and Wendy’s bags, while Anna grabbed her own. Anna was still a bit groggy from the nap, so she shuffled behind them looking a bit like the third wheel. At check in, the clerk saw the note on the reservation about the recent breakup. He mistook Wendy and Dave for the couple and handed out the room keys accordingly. Before Dave could correct him, Anna interrupted with a quick “thank you,” and ended the conversation.

Just then, Wendy’s phone rang and she went off to a quieter part of the lobby to answer it. Dave cornered Anna. “What’s going on, Anna?”

“Well,” Anna said with a wry smile, “we always say that hotel sex doesn’t count.” Anna always got horny in hotels, and they had experimented with bondage, anal, and some other kinkier stuff. Their sex life at home wasn’t dull, but Anna didn’t like to be that adventurous in familiar surroundings. At first, Dave was confused about the dichotomy and they had a lot of frustrated fights. Early on in their marriage, Dave and Anna had made a deal that anything done in a hotel was not, necessarily, fair game at home.

Today, Anna was in a funny mood and honestly didn’t think Dave would really go along with it. She figured she could have a little fun with him and Wendy.

Dave was never one to back down from a dare, so he went along out of pride and a little curiosity. He really wanted to see how Anna would break it to her friend. He sized up his wife, and met her wry smile with his own. “Okay, I’m game,” he said.

When Wendy came back, Anna was undeterred and simply said to Wendy, “I’m going to loan you this big, hulking hetero for a few days. Have fun!” She nonchalantly grabbed her luggage and left the lobby for her room. In the room, she opened her side of the two interior doors connecting the adjoining rooms and anxiously waited to eavesdrop on her husband and Wendy.

Wendy and Dave arrived a few minutes later and were obviously hamming it up, fully expecting Anna to be listening. “Oh Dave! Mwah mwwah,” Wendy cried, making childish kissing noises. “Oh my! You’re just so BIG!”

“Oh, Wendy your tits are gorgeous!” He wasn’t lying.

When Anna refused to react, Dave and Wendy escalated the theatrics. Dave stood at the foot of the bed and started thrusting the bed frame into the wall with his knees. Wendy quickly joined in. Still fully clothed, she climbed on the bed and went down on all fours in front of Dave. Dave grabbed her hips and she grabbed the headboard and they frantically pounded the bed into the wall.

“Oh, Dave, yes, give it to me! Give me your big cock!” On the other side of the interior door, Anna rolled her eyes.

Dave and Wendy were only playing, but there is only so much of that kind of playing two heterosexual people can do before nature starts to take over. For Wendy, it had been over a month since she had a real cock inside of her and that was with Matt. Being gay, he really wasn’t that into the sex. She could feel herself getting more and more turned on, but the freedom of being in a hotel room and going along with the joke got the better of her judgment. When Dave’s raging hardon started pressing on her pussy from behind, it suddenly became very real for both of them.

They both jumped back from each other and blushed furiously. An awkward quiet fell on the room. Wendy quickly jumped off ankara escort the bed and mumbled something about wanting to take a shower before dinner. She headed across the largish room toward the bathroom. Dave’s now obvious erection was pointed toward the window, as Dave was suddenly captivated by the scenery.

On the other side of the adjoining doors, a few feet from the suddenly quiet bed, the silence bothered Anna more than the mock thrusting. She pressed her ear against the adjoining door for what seemed like 20 minutes. “What just happened,” she thought. For a moment, she swore she heard kissing, or was it heavy breathing. She couldn’t hear the shower running, or at least, not so that she could tell it was their shower. Her mind raced. “Was Dave fucking my best friend? Were they just playing with me? Did they realize the silence would bother me more? I bet that’s it. Well, I won’t give them the satisfaction.” After a long pause, she would hear the bed creak, or a dubious noise and repeat the cycle. At one point, she could have sworn she heard her husband grunt and cum. Her nervous cycle was broken by a firm knock at the door.

In the adjoining room, Wendy had finished her shower, which included a wonderfully stimulating release, with the help of the shower head. While she was showering, Dave had quickly jerked off, trying—unsuccessfully—not to think of the soft feel of Wendy’s fleshy hips and the swaying of her massive breasts as he mock fucked her. Wendy came out of the bathroom wrapped tightly in a bathrobe, drying her hair. They again avoided eye contact as Dave slipped in to the bathroom to take his own, colder, shower.

Wendy heard the adjoining room’s interior door shut, and realized that Anna and Dave were still playing their marital game of chicken. She was hoping one of them had given up, so she could treat herself to a good rub in the privacy of her own room. Curious about the state of play, she opened her side of the double door and listened in. Suddenly, she remembered that, before the breakup, she had booked a couples’ massage for her and Matt. Her face turned beet red as she realized what was about to happen.

In Anna’s room the person knocking announced that he was there for the massage. At first, Anna thought about getting Wendy and clearing up the mistake. After taking a glance at the masseur, though, she quickly decided that accepting the massage was payback for Wendy and Dave extending their theatrics.

The masseur was a tall, well built, handsome young man. He was toned, but not overly muscular, and very easy on the eyes. He was wearing athletic shorts, a white polo shirt, and sneakers. Anna couldn’t help but think he looked like a personal trainer she knew from somewhere. Todd moved into the room with a quick smile at Anna. “My name is Todd, I’m the masseur you requested. You must be. . .Wendy?”

Anna decided she didn’t want him using the wrong name the whole time. “Actually, it’s Anna.” Todd was used to people booking under fake names. They never realized how awkward it is to have someone call out a fake name while they’re trying to cum.

“No problem, Anna,” the studly Todd said with an easy smile. “It’ll take me a few minutes to set up, so you can grab a quick shower if you like.” He noticed her wedding band on her finger, and smiled to himself.

Anna took a quick, but invigorating shower. In the next room, Dave came out of his shower at about the same time as Anna, and found Wendy with her ear pressed against the door. “What is she doing,” Dave asked in a low whisper.

Wendy jumped out of her skin, forgetting that Dave was in the room. “Dave, I should tell you something, it’s a bit embarrassing.” Dave sat on a chair near the adjoining door while Wendy sat on the bed. They were both still in their robes. Wendy tried to explain without sounding crazy or slutty.

“Matt and I used to do some, well, funny stuff in hotels. It kind of makes more sense, now that I know he was gay.” She rambled a bit and Dave brought her back. “Anyway, one of the things Matt liked to do was to have masseur come to the room for a couples’ massage. I would get a massage for an hour, and then Matt would get one.”

“Okay. That’s not weird.”

“Well,” Wendy added, reluctantly, “they were sort of ‘special’ masseurs.” Dave’s eyes widened. “Yeah. I don’t know how he found these guys, but they would, well,” Wendy tried to find the words. “We’d *both* get a happy ending.” Dave’s jaw dropped. A thought suddenly hit Wendy. “It should have occurred to me that Matt was always finding guys, but I guess…”

“Hold on, my wife is in there with a male prostitute?!?”

“Ssh!!” Wendy pointed towards the door. “Kind of,” she reluctantly confirmed. “I mean, I never. . .just, you know,” she held up two fingers and pointed towards her groin in a rubbing motion. “But, I’m pretty sure these guys would go as far as their clients will let them.”

Anna came out to find Todd shirtless, wearing only what looked like a tight swim brief. She could easily make out the lines of his very escort ankara large penis, and found herself staring. She took a deep, nervous breath and took in the rest of his body. He was gorgeous; completely hairless and every muscle perfectly sculpted. He looked like an Olympic swimmer.

He motioned towards the bed, where towels were laid out, covering the bedspread. She hesitated at first, until Todd said, “I’m sorry, is this not what you wanted?” Hearing this as a dare, Anna decided to play it cool again.

“Either Wendy and Dave are setting me up,” she thought to herself, “or I’m going to have an interesting conversation with Wendy later. Besides, if Wendy’s done this, at least I’m not the only one,” she rationalized. Anna moved past Todd toward the bed, and suddenly realized that she had not put on any underwear when she finished showering. She again hesitated, standing still with Todd immediately behind her. Before she could speak, Todd’s strong, firm hands had found her shoulders and effortlessly dropped the robe to the floor. His warm body pressed against hers. As his bulging member pressed against her bare bottom, she felt an electric shock rush through her. She composed herself and laid face down on the bed, completely naked.

Wendy and Dave heard the muffled voices and then heard the bed creak. They both swallowed hard and looked each other in the eye. Dave was realizing that this was not the kind of guy who brought a massage table. The both crept over to the door to listen. At first, they heard only muffled voices. They couldn’t make out many words, but it had that pace and patter of small talk. Slowly that died down and was replaced by Anna’s moans of delight.

Todd was working on her thighs and calves. As he often did, he had raised the temperature in the room to about 90 degrees. Beads of sweat were starting to trickle out of Anna’s skin, and were mixing with the oil, making her taut skin glisten. Todd was expecting a couples’ massage but figured her husband was off golfing or something. If this housewife wanted the full two hours to herself, so be it. It wouldn’t be the first time a husband left his wife alone at a hotel.

Todd was in fact bisexual, but loved pleasing women with his hands. Not many women went for the “full service” option, but he was always ready to go as far as they wanted to go. He was pleasantly surprised with Anna’s pretty, suburban housewife vibe, and she seemed to keep herself in pretty good shape. He also loved the taboo nature of massaging another man’s wife. He started preparing himself for a full service treatment as Anna’s legs slowly began to drift further and further apart.

Anna was drifting off into a blissful state as Todd massaged her legs, slowly moving up her inner thighs. He had loosened her up by starting with her neck and back. Now all thoughts of her husband, where she was, and who shouldn’t do what to whom, were all fading into the distance. With each pressing stroke, she felt her legs spread, ever so slightly. At first, she fooled herself into thinking they weren’t really spreading. Then she convinced herself that it was just Todd’s stroking motions that happened to be pushing them, ever so slightly, apart. She told herself that Todd was a professional, and he knew what he was doing. What harm could a little touching do? Then she reminded herself that Wendy had obviously done this before, so she wasn’t going to be too prudish.

She felt Todd gracefully slide around the side of the bed as his strong, firm hands reached her buttocks. He lifted and separated her buttocks, pulling them up towards her back and then letting them bounce after each stroke. The vibration shuttered through her, reminding her of the feel of a man powering into her from behind. With each stroke, Todd’s hands would go deeper and her legs would spread wider.

Todd was intentionally going at an agonizingly slow pace. Anna’s pussy was aching to be touched, but each stroke seemed to be getting imperceptibly closer to her waiting sex. She was begging for release. Her hands were at her sides, clenching as Todd approached her lips. As he moved away, teasing and tormenting her, her hands would spread wildly, almost grasping at her tormentor.

Todd smiled to himself as he watched Anna squirm, trying to make him touch her on each stroke. She arched her back, trying to press her lips onto his hands. She subtly wiggled her tight little housewife ass, begging for him to just glance across her pussy. He loved this part, and extended it longer and longer until his own erection was at full strength. How she reacted next would be the key to seeing how far Anna would be willing to go.

Todd’s fingers finally found the outside of Anna’s labia and she let out a low, desperate moan into the pillow.

“What was that?!?” Dave exclaimed in a whisper. His own hardon was in danger of poking out of his robe.

Wendy was lost in her memories of erotic massages past, and had subconsciously let her robe open more than modesty would allow. Dave’s question brought her back into ankara escort bayan the hotel room. “He, he’s umm, well, he just touched her down there.” Wendy knew that this was the turning point. During her first massage with Matt, she jumped up and said “What the hell?!” That ruined the romance that night. Matt and she had a long talk, and the next time, she was more receptive to that first touch. Privately, she was amused and impressed that Anna was so liberal.

Dave wasn’t as surprised, but was still trying to cope with this being real. Dave and Anna had talked about having other sex partners, usually as just a fantasy. Anna would tell Dave about a hunky guy at work or in the gym, and they would make up erotic stories about him fucking Anna or a threesome. They had never acted on those fantasies. Well, not until today.

In the next room, Anna was lost in Todd’s touch. His fingers would pinch her lips together and then press on her clitoris, building her orgasm higher and higher. With his other hand, Todd freed his erection from the briefs by releasing the breakaway clasp. He casually maneuvered his exposed cock so that its head and part of his length rested on her naked ass. He watched Anna’s hand grasping wantonly. He smiled, placing his balls and then his rigid cock onto Anna’s searching hand. Anna wrapped her hand around it and, realizing its size, let out another deep, low, naughtier moan. Todd knew he had a green light to keep going.

“That didn’t sound good,” Dave said to Wendy. She glanced at him, realizing that he may not be a willing participant in this. As quickly as she held this thought, she noticed the tent pushing out of his robe.

Wendy was still horny from the role playing earlier, and hearing Anna get fingered in the next room was not helping matters. She decided to provoke Dave and see where it went. “You seem to like what you’re hearing,” she said, directing her eyes and his toward his bulge. “Do you like the idea of a strange man touching your wife?” Now it was Wendy’s turn to show her naughty, wry smile.

Dave swallowed hard. Wendy drew closer to him. She pressed her large breasts against his right shoulder and let her robe open slightly, revealing the tops and sides of her large breasts. She placed her left arm over his shoulders and drew her right hand reach across his chest. Pressing her moist womanhood against his thigh, she whispered in Dave’s ear, seductively, “by now, he’s got his cock out.”

Dave nearly whimpered. His throat was incredibly dry for some reason, and his stomach was at his feet. Somehow, his right hand found Wendy’s waist. She refused to let up. He could feel her warm breath on his ear and the warmth of her breasts and pussy against him. Their naked bodies were separately by nothing by the lightweight cotton robes. “He takes his cock out, right after his fingers slip into her naughty little pussy.” She delighted in watching his cock twitch and dance under the robe. “It’s so big and hard, a girl just can’t resist.”

In truth, Wendy had only once grabbed a masseur’s cock. The last time she and Matt were in a hotel together. She was surprised it didn’t go further than it did. The masseur still only fingered her, even though she was willing to go further that night. Then again, her boyfriend was in the room. She wondered what might stop Anna now.

Through the door, Dave heard his wife’s moans of pleasure build. Suddenly, they were joined by Todd’s.

“Mmm. Yeah, do you like that, Anna?” Todd was enjoying the handjob, but needed to keep building Anna’s orgasm.

“Mmmm hmm,” was all Anna could manage as she stroked Todd’s long, thick cock. Her back was arched, and her ass was high in the air as Todd’s big, thick fingers easily slid in and out of her wet pussy. If she had any inhibitions, they had left her alone with Todd. She could not see Todd’s cock, but knew it was bigger than her husband’s. A lot bigger. She split her focus between the magic he was doing with his fingers and her growing lust for this new, strange cock. As the waves of her building orgasm hit her, she would momentarily stop stroking, grabbing his cock firmly as if she was holding on to a ship in stormy seas.

“Tell me what you like,” Todd demanded

“Your cock, it’s so hard. I want your cock,” Anna was gasping and pleading.

“And what do you want?”

“I wan…” the waves were building, stronger and closer together, “I want, ooooh, oh God, I wanntt, uh, oh!” Todd quickened his pace. Anna was griping his cock tightly now as he finger fucked her with one hand and caressed her naked breasts with the other. As she hesitated, he grabbed her tangled hair and pulled gently. Her head lifted off the pillow, she locked her eyes on his. Hers were filled with lust.

“Tell me, what do you want?” Todd locked in on her eyes and bit his lower lip. At the same time, he pushed firmer and harder into her, fucking her slow and deep with his fingers.

“Fuuuuuck meeee, pleeease,” Anna burst out as her orgasm hit her. “Fuck me, fuck me, Todd, please fuck me,” she begged, throwing her hips back onto his waiting fingers. She was desperately groping his manhood as he continued to finger her. Todd didn’t relent he onslaught until Anna collapsed, convulsing on the bed. His fingers were coated with her wetness.

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