My Dare Ch. 02

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Ara 6, 2023 // By:analsex // No Comment

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Jenny wore another of Steve’s shirts as she left to join her roommates. She carried her other clothes and a bottle of wine that Steve had given her to welcome them to the island. She felt like she had just finished a marathon, even though she hadn’t run far that morning. Steve had said that he would make reservations for dinner, so she figured she had time for a nap.

When she walked into the condo, Amber was doing her toenails on the couch and looked up with a leer. “We thought maybe he’d killed you,” she joked. “Are we going to share, or do you want to keep him all to yourself?”

“I think there’s plenty for all three of us,” Jenny replied. “Speaking of which, where’s Susan?”

“In here,” Susan yelled from the bathroom. “I just finished my shower. It’s free for anyone who stinks like they just had sex. And leave me out of the equation. I’m not ready for casual sex, even if Steve is a hunk.”

“From what we heard, there was nothing casual about that sex,” laughed Amber before Jenny could take offense. “My Dare-Susan will fuck Steve within two days!”

Since they were in college, the three women had played a game they called My Dare. When one of them dared one or more of the others, they had two choices. If they complied, the one who issued the dare had to wait on the others for a 24-hour period of their choosing. If they didn’t, then they had to be her slave for 72 hours. The three had gotten pretty good at being Masters, so dares were always followed through on; no one wanted 72 hours of slavery. Jenny still remembered the three days she waited hand-and-foot on Amber, wearing nothing but a short French maid’s outfit with crotchless panties. Amber chose that time to have several of her male engineering classmates over for study sessions. Amber had taken great pleasure in having Jenny pick up strategically placed books across the room.

Besides, when a new dare was issued by any of the three before the darer paid the price, it took precedence. So there had been only rare occasions when any of the three had actually had to be a slave over the last few years. Now My Dare was used as a way to say “Loosen Up, Do Something Risky.”

Susan turned beet red and stormed back into the bathroom. Jenny knew that Susan would comply, and hoped that secretly she wanted to.

“That reminds me,” Jenny said, “Steve is taking us to dinner tonight. He said we should dress however we wanted, but he would be disappointed if we wore too much. I told him that Amber would take that as a challenge, but Susan might look like she was in Alaska in February.”

Susan had come back out of the bathroom. “If I’m going to fuck Steve in two days, I’m going to need help from you two. Jenny, you can’t wear him out; and Amber, you’ve got to wait your turn.”

“Not if you wait too long,” Amber replied. “We only have a couple of weeks and I want my share of that cock. And oh yeah, that tongue!”

After some discussion they decided to all wear sundresses. Amber wanted to go without panties and Jenny agreed. Susan wasn’t ready for that so the other two didn’t press the issue.

Jenny jumped in the shower, cleaned off, then put Steve’s shirt back on before lying down for a short nap. Amber and Susan put their suits on to spend some time on the beach.


I had made a reservation for four for 7 that evening at a nearby seafood restaurant. Jenny said she needed another shower and also needed to unpack. My last request before she left was to get first and last names for all three women under the guise that we needed to know each other better. After Jenny left, I placed a call to a colleague in Denver, gave him the names, and asked him to get background checks on each. I had a business idea in mind, but wanted to make sure that I was getting involved with legitimate women.

As I finished some other business on the phone, I heard squealing outside. I went out on the lanai as Susan and Amber ran back toward the condo from the ocean. Both were soaked and looked great in the same suits they wore for the short time in my living room. Amber saw me and waved. Susan saw me and didn’t. “Hi, Steve,” Amber yelled. When she was close enough to lower her voice, she continued, “What the hell did you do to Jenny? We thought you were killing her up there and now all she wants to do is sleep.”

I laughed and replied, “A gentleman never tells; you’ll have to ask her.” I wanted to make sure that they knew of the dinner plans, and Amber assured me that they did. As they departed and headed into their unit, Susan surprised gaziantep escortlar me by waving goodbye quickly.

I had rented a Mustang convertible, and we all piled in for dinner. I had worn khaki shorts, loafers, and a Hawaiian shirt-standard fare for Hawaii. All three women had worn short dresses with island prints. While Jenny’s and Susan’s had spaghetti straps holding up the tops, Amber chose a strapless style that exposed her shoulders and much of her upper chest. All three wore fancy flip-flops and had their hair down.

Jenny sat in front with me, Susan sat behind me, and Amber sat behind Jenny. We put down the top since the evening was perfect. Jenny quickly slipped off her shoes and put her feet up on the dash. As we left the Napili area and turned onto the main road, we picked up speed and the wind started whipping through the car. Jenny’s dress quickly blew toward her chest, revealing that she was not wearing panties. She spread her feet on the dash, allowing the breeze to caress her sparse pussy hair. I reached over without taking my eyes off the road and placed my hand on her mound, trailing my middle finger down the top of her slit to nestle in the folds. I looked in the rearview mirror to see Susan and Amber exchanging whispered comments. Suddenly Amber’s bare foot was poking at my arm, forcing me to remove my hand from Jenny’s warmth. “I’d say to get a room, but then we never would eat,” Amber shouted over the wind noise. “I get to ride up front coming home.” With that she raised her foot to the top of Jenny’s headrest, and I quickly glanced back to see that she too had left home without panties. Her bare pussy literally glowed in the afternoon light, and the little heart was quite fetching. I couldn’t see Susan, but hoped she had been persuaded to follow along with her roommates.

We arrived at the restaurant for dinner during which the girls behaved themselves reasonably well until the second bottle of wine. I learned more about them, and they learned that I was, like them, an engineer. Like Susan, I too had sold a business and was “between jobs”. I didn’t tell them that I had more money than I knew what to do with-I was not anxious to find out that any of these women were gold diggers.

I sat next to Jenny and watched as she occasionally exposed her pussy when I was the only one who could see. Amber, across from me, kept running her bare foot up my leg. At one point, I slipped off my own shoe and climbed her leg with my toes, thinking I’d get her back a little. Instead, she reached down, grabbed my foot, and slid forward in her seat enough to insert my big toe in her cunt. Susan was witnessing this lewd act and almost choked on her mahi mahi. “Amber,” she hissed, “stop that! Remember what we talked about.”

“Oh, don’t be a spoil sport,” Amber answered. But she released my foot and straightened up in her chair. I wondered just what they HAD talked about.

The rest of the meal went uneventfully; I paid and we returned to the car. The sun had gone down and a few clouds threatened rain. We left the top up and Amber sat in front. As soon as she got in the car, she pulled the hem of her dress up and over her head and tossed it in the back seat, where it landed across Susan’s and Jenny’s laps. She turned to look over her shoulder and said to her roommates, “My Dare-get naked.” I looked at her curiously as Jenny pulled her dress over her head like Amber had and Susan pushed the straps off her shoulders before pushing the dress down and over her hips. Jenny was naked while Susan still had on light blue panties that she was now sliding off. All three dresses and the panties were thrown behind the back seat.

Amber explained My Dare-how they had played it for years and what the penalties were.

“Sounds fun-can I play?” I asked.

“Sure. Get your clothes off,” she ordered.

I was still in the restaurant parking lot, so I unbuttoned my shirt, pulled it off, then unzipped and pulled my shorts and underwear down. After some effort, I was as naked as the ladies and my shirt, shorts, underwear and shoes were in the back. Since Amber had been “helping” me get undressed, my cock now touched the steering wheel.

“Let’s go,” I said, and we pulled away. Instead of going home, I headed the other way. There were some less-traveled roads that I wanted to find. As we saw fewer cars, the weather started to clear. I pulled over and only one car whizzed past as I lowered the top and windows of the convertible. As I pulled back onto the road, I purposefully traveled at a slower speed. As the occasional car came up from behind, their lights would illuminate the naked shoulders of Jenny and Susan. Then they would pass as the darkness hid the four of us. At first, the girls would slink down in their seats as cars would pass, but soon all three were sitting up and waving, knowing that they were protected by a certain anonymity as island tourists.

As the evening wound down I turned toward our condo, and we eventually pulled into the parking lot and found the last stall.

As Jenny was reaching over the seat to retrieve our clothes I said, “My Dare-we all walk naked to my condo for a nightcap.”

Jenny asked, “Can we carry our clothes?”

“No, leave them here. I’ll get them in the morning,” I said.

We got out of the car, and I led the girls on a leisurely stroll down the middle of the parking lot, along the sidewalk in front of several condos with lights on, and eventually up the stairs to my unit. I thought, “If only our neighbors knew what they just missed!”

Entry to my condo was a code key, so I let us in, holding the door like a gentleman. I watched the three beauties walk past. I was secretly pleased that Susan had gotten into the swing of things. In fact, I could swear that she purposefully touched my thigh as she brushed past into the room.

I made margaritas with the blender in the room. Amber and Jenny took the two chairs in the room, leaving Susan and me sitting on the sofa. I was a little surprised that neither girl sitting across from us flashed their cunt at me, rubbed their tits, or otherwise lewdly displayed themselves. On the other had, Susan was nervously fidgeting with her drink and giving me sidelong glances as we quietly finished our margaritas.

When I got up to refill glasses, Amber and Jenny quickly sprang up to excuse themselves-both claimed to be “really tired.” When I turned to Susan, assuming she would join them, she held out her glass expectantly. As the other two walked out I saw them exchange a knowing look with Susan.

I refilled her glass as Susan returned to the couch. “All right,” I said, “what’s going on?”

Susan stared into her drink for a moment before looking up at me with tears in her eyes. “I’m supposed to seduce you; Amber dared me earlier today. But I’m really not ready.”

I looked at this gorgeous creature before me, wearing nothing but the moisture dripping off her glass. I hated to ask the question but I had to. “Susan, tell me how the rules work for My Dare. You said that everyone accepts the dare and that the ‘darer’ owes unless another dare is issued. But what if the dare hasn’t been performed before the next dare is issued. Wouldn’t that negate the dare?”

Susan jerked her head up in surprise. “I’m not sure-our dares are always carried out immediately. This is the first time a dare has been given for a longer period, and this is the most dares that we’ve issued so close together. I suppose that if the ‘darer’ is off the hook, the ‘daree’ should be too.”

“Well, I hate to consider myself ‘the hook’,” I laughed, “but that’s what I’d say too. So the pressure’s off; enjoy your drink and we’ll call it a night.”

Instead of gratitude, I got a look that could kill. “If you think I’m ugly and want me to go, you don’t have to come up with clever excuses,” she spat. “I know I’m fat, but I still have my dignity!” She jumped up before I could stop her and stomped into the kitchen to toss away her perfectly good margarita.

I stood up and quickly followed her into the kitchen. It was clear that she needed reassurance and a firm hand. As she stood at the sink I grabbed her upper arms to hold her and wedged my hard cock hard between her ass cheeks. “Does this feel like I don’t want you?” I growled in her ear. I pushed her forward so she was leaning over the sink, which shoved her ass back at me. I moved my hands down her arms, pulling her wrists together behind her back. Grabbing them with my left hand, I reached around to her dangling tits and roughly massaged them with my right hand. At the same time, I raised and lowered my body to run my cock up and down her crack.

Susan moaned and shook her head from side to side, struggling half-heartedly. I released her tits and lowered my hand to her thigh, pulling her leg up to the count top. Her heel hooked over the edge, and her right leg was now straight out to the side. As I pulled back, I released her hands and sank to the floor, bring my face even with her now wide-open pussy. Taking an ass cheek in each hand, I pulled them apart to expose her more fully and roughly licked and bit at her cunt and asshole. As I held her by the ass and noisily slobbered, she pulled herself further over the sink. She now was stretching on her tiptoes of her left leg, so I reached down and lifted that leg toward the counter as well. When her left heel found the counter, I sat back to enjoy the most amazing view I’d ever seen. Susan was stretched from one end of my counter to the other; her ass was slightly below counter level as she held on to the sink faucet. Her wide-open ass cheeks showed my handiwork on her holes, which glistened and dripped. I had never seen anyone do the splits like that and I told her so.

“Shut up and fuck me,” she groaned.

I stood and placed my hands below both thighs, helping her to maintain her position. My cock easily slid into her gaping pussy, and I slammed forward and up in one stroke to bury myself. Susan hissed, then howled as she came. Her inner muscles throbbed on my cock as I held myself in her. I began to pull back but she reached back with her left hand and held me in place. “Just move up and down,” she commanded, so I squatted slightly and straightened several times to work my cock over her clit.

After a second orgasm ripped through her, she pulled forward enough to release her heels from the counter. She maintained her position over the sink as her legs pulled back and I held them at my sides. I was still buried in her and began to move back and forth, holding her like a human wheelbarrow. Her tits hung in the sink, and since I was now supporting and holding her by the legs, she was able to push off the sink edge and lift her abdomen off the counter, easing the pressure on her ribs. Her back glistened with sweat as I moved in and out of her. When she tightened up with her third orgasm, I lost it. My cock slipped out of her as I shot my jism over her but cheeks. I moved her legs up and down as I rubbed my cock with her cunt, spurting upward and finally changing to a dribble.

I eased Susan’s feet to the floor and helped her to stand. She gingerly turned to hug me as we kissed. I stroked her ass, rubbing my cum in as though it were lotion. My cock was nestled against Susan’s pussy, and she swayed to let her pubic hair caress my softening member. We both were dripping from our workout, which added to the erotic nature of our embrace.

I finally pulled back and looked Susan in the eyes. “You’ve just set the bar at a new level for me, so I hope I never hear you berate yourself again,” I said with total honesty. “You are an amazing woman with a perfect body. I’m making it my mission for the remainder of this trip to make you forget your ex-husband.”

“What ex-husband?” Susan replied, smiling.

I suggested we cool off in the ocean and was glad to see that Susan unabashedly joined me as we scampered downstairs and ran across the sand to jump in the water. We copped feels as we jumped in the waves, then quickly rinsed off under the cold water shower before kissing goodnight and heading to our units.


Susan quietly let herself in the girls’ condo and was immediately confronted by her two eager roommates. Amber and Jenny had put on Steve’s shirts, and Susan was still damp from her quick shower. “Hope that means you’ve been ‘rode hard and put up wet’,” Amber laughed. They both could see a different glow to their blonde friend.

Susan sighed and smiled, “I almost blew it. I told Steve that I had been dared to fuck him, and mister nice-guy found a technicality in our dare game that let me off the hook. So I played the ‘You think I’m ugly’ card. Boy, did that work!”

Susan described the action as Amber and Jenny listened with rapt attention. At one point, Jenny asked Susan to demonstrate her position, so the girls cleared the sink counter. With some help from Amber, who was only too glad to hold Susan’s ass in place at the sink, she was able to show them how she first took Steve’s cock, then Amber and Jenny held her legs as she demonstrated the final position. “I’ve never cum three times so fast,” Susan admitted as she finished describing her evening.

“Now we know Steve likes circus acts,” Amber laughed. She knew that she was less limber than the other two, but that wasn’t going to stop her from being next. She reminded her friends that it was now her turn, and all three hugged in agreement as they headed to bed.

Jenny found herself tossing and turning as she imagined the scene with Susan upstairs. She found herself focusing less on Steve than on Susan and that wide-open pussy she had witnessed in replay. She would have been surprised to know that Amber lay in the next bed with similar thoughts.

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