In our last story, "The List," Mikki and I created a list of sexual challenges and succeeded in completing four. With twenty more to go, we had plenty of room for both intimacy and excitement.

Previously, Mikki and I had wrapped up the story by rolling a ten on the dice, which led us to the scenario "baring it all for the pizza delivery guy." Given we ordered pizza monthly and had scoped out one particularly good-looking delivery guy, we knew this challenge would be fairly simple. We waited in the living room, dressed only in robes. When the doorbell chimed, Mikki peeked through the curtains and confirmed it was him. We positioned ourselves by the front door, dropped our robes, and hung them nearby. I opened the door, and the look on the delivery guy's face was absolutely priceless.

Without missing a beat, Mikki took the pizza while I handed him the money. Before he left, I asked, "Would you like to come inside for your tip?" He followed us into the lounge, with our partners sneaking glances from behind the kitchen hatch. We instructed the delivery guy to take a seat, unzipped his pants, and revealed an impressive cock. Mikki took it in her hand and began to suck his cock.

I asked him if he was enjoying his tip, to which he eagerly nodded and replied, "Yes, very much." Mikki lifted off his cock, moving it towards my mouth, and I eagerly took him in, playing with his balls.

Feeling incredibly aroused by the situation, I removed his shoes and socks, then slid off his underwear and straddled him. Mikki held his cock, guiding it into me as I lowered myself down until he was fully inside.

As I bounced up and down, he thrust upward, pushing his cock deep into me. I could feel my orgasm building, my nipples stiffening. Knowing I had three pairs of eyes watching me, I climaxed, feeling a wave of pleasure.

Building up our pace, he thrust as I bounced, grabbing my hips and saying he was about to cum. I encouraged him on, and with a final thrust, he erupted, filling me with his warm seed. As I got off him, his cock fell onto his stomach, and Mikki took him back into her mouth, licking him clean of our combined juices.

After we recovered, we assisted him in getting dressed. Still naked ourselves, we accompanied him to the door, each giving him a farewell kiss. Mikki then mentioned that it would be her turn on the next deliver.

When the door shut, the men immediately rushed Mikki and me down the hall and into the lounge. We eagerly assisted as they removed their clothes. Without ceremony, they bent us over the couch and pushed their hard cocks into our eager pussies. It was over quickly; I came as James spilt his cum inside me, with Mikki and Bobbie following suit shortly after. Afterward, I cleaned Bobbie's cock and Mikki did the same for James.

We gathered in the lounge with a bottle of wine and four glasses, sipping our drinks and eating cold pizza. James mentioned that he had enjoyed watching Mikki sucking the other guy and seeing me ridding him. Bobbie nodded in agreement. After finishing the pizza, Bobbie instructed us, "Alright, ladies, go to your bedrooms and get what you need." Since the last challenge, Mikki and I had gone shopping, and she had picked out her own paddle. It was similar to mine but a bit wider and with holes. She had it engraved with "only for Mikki."

We returned to the lounge, paddles in hand, and gave them to our partners. Still naked, we bent over their laps, ready for our punishment. We each received twelve hard smacks on each cheek. Then, we picked up a tub of cream each, which we handed to our guys. James began applying it to Mikki's cheeks. Bob looked at me and said, "Not so fast, Carol." Confused, I asked, "What?" Bobbie reminded me that the challenge was to flash the delivery guy, not to fuck him. He told me to get back over his lap.

Expecting him to apply the cream, I instead received one hard spank on each cheek, followed by an additional twenty-two spanks with the paddle. This was the first time I had received twenty-four paddle spanks on each cheek, and it hurt immensely. I knew I'd be sore for the rest of the week. Bobbie then rubbed cream into my very sore bottom.

Mikki and I then sucked our respective partners cocks, each receiving a mouthful of cum.

The following morning, I examined my backside in the mirror. It was the reddest I had ever seen and hurt a lot, but I understood I deserved it. I asked Bobbie if I had gone too far, and he assured me I hadn't; it was part of our agreement, and he found it exciting to watch. He also reminded me that choices come with consequences.

On Sunday, the guys headed to the club while we got the roast cooking, and with a bottle of wine we sat down to review the list. We crossed off number ten—labeled “bearing all for the pizza delivery guy”—each of us rolled a die: Mikki went first, then I did. The dice showed a five and a three, adding up to eight, which meant we were to have sex with a man at least twice our age. At that time, Mikki had just turned twenty‐two and I was still twenty‐one, so the guy had to be at least forty-four. We agreed that we needed to discuss it fully with the guys that night to get their opinions and that it had to be the right man—not just anyone who fit the age gap, but someone with a handsome personality and a real connection.

I mentioned to Mikki that Bobbie and I were planning a holiday in January and that we’d like them to join us. Mikki thought it was a brilliant idea. She planned to ask her mom when she picked up Oliver later, and we decided to talk it over with the guys that evening, along with discussing the challenge. Mikki and I hadn’t been together for over a week, and after getting undressed we climbed into bed.

We began by kissing each other passionately. I took her breasts into my mouth, gently sucking and nibbling on her nipples. As I moved down her stomach, I traced a slow, deliberate lick from the lower part upward toward her pussy, then retraced my path, sliding my tongue playfully. Next, I focused on her clit, softly sucking it and drawing a few moans of encouragement from her. I continued to work on her pussy while my thumb caressed her swollen clit. Her moans grew louder and she began to buck, so much so that one of my fingers became moistened; I then slipped it into her arse. All the while, I alternated between licking her pussy and rubbing her clit with my thumb. She grabbed my head and pulled me closer as she exploded into a shuddering, moaning orgasm—her thighs locking around my head and forcing my head deeper until I struggled to breathe, as the aftershocks of her pleasure continued to ripple through her.

After a while, she released her grip on my head and her thighs relaxed. I moved up to kiss her, and she thanked me, saying that was exactly what she needed. She then returned the favour with an equally wonderful climax.

After we showered together and each reached another climax, I finished preparing dinner while Mikki went off to get Oliver.

They all arrived home together, and the five of us gathered around the table for our traditional Sunday roast, with little Oliver happily sitting in his high chair. While the guys cleaned up after the meal, Mikki and I entertained Oliver—with him happily showing off his new soft toy from his nanny, clearly delighted by it.

Later, once Oliver had fallen asleep, we moved to the lounge with a glass of wine in hand. Mikki mentioned that her mum was willing to look after Oliver while we took a holiday. She also recalled that a friend had recently visited Tenerife and recommended it, even admitting that she’d tried a nudist beach for the first time. I told Mikki that I was curious to try that as well, and she agreed.

The guys quickly warmed to the idea of spending two weeks in the Canaries, a plan that also served as a belated celebration for my twenty-first birthday and for Mikki and James’s engagement. Soon after, Mikki explained our latest challenge, adding that we had already agreed that if the guys weren’t completely on board, we’d choose a different one. Mikki and I then decided to head into the kitchen and let the guys discuss it among themselves.

About half an hour later, we opened a new bottle of wine and returned to the lounge. As I refilled everyone’s glasses, I asked for their thoughts. After briefly looking at me and Mikki, James remarked, “Seems like you two girls need to find an older guy to have sex with,” which was his way of saying they were both on board.

I got up and began to undress Mikki, and she assisted me in removing my clothes. Once we were both naked, we turned our attention to the guys and helped them undress as well. I performed oral on James while Mikki did the same for Bobbie. Then we seated them on the settee, where I guided James inside me as Mikki welcomed Bobbie in a similar fashion. We moved slowly, savoring every sensation.

After a while, the roles reversed—the guys flipped us over, leaving us kneeling on the settee as they took their positions from behind. Before long, as James filled me with his cum, I reached climax with his hard cock deep inside me. Once Mikki and Bobbie had both climaxed, we moved into a sixty-nine position, sharing the taste of our partners’ cum and enjoying another wave of pleasure. Finally, I took Bobbie to bed, and we made love while listening to the others in the adjacent room, immersed in their own passionate activities.

On Monday morning over breakfast, I mentioned to everyone that I’d stop by the travel agent to pick up some brochures. They reminded me that I already knew what the requirements were—if I found the right holiday, I could book it. Oliver and I then headed to the travel agency. While he enjoyed browsing the colorful pictures in the brochures, I explained to the agent exactly what I was seeking. We weren’t after an apartment; we just needed a proper break. As I reviewed the available holidays, I discovered a lovely four-star hotel offering half-board accommodation. It was built just a year and a half ago, featured three outdoor pools, dining areas, and bars right on the beach. The agent noted that the hotel had received excellent reviews—old enough to have sorted out any initial teething problems yet still modern and appealing.

She presented several room options, and I selected a corner suite that would accommodate all of us. The suite featured two queen beds, a sitting area, a bathroom with a separate toilet and shower, and, because it was a corner room, a wraparound private balcony. It was perfect and cost less than booking two separate rooms. I paid the deposit, and the agent informed me that since our departure was approaching, I needed to pay the remaining balance within two weeks, though I could change the booking up until seven days from that day.

That evening, I shared my find with everyone, and they were thrilled at the idea of us all staying together for a relaxing holiday. James even handed me a cheque to cover his and Mikki’s share (yes, we still used cheques back then). On Friday, I decided to settle the balance by giving the agent a cheque, and she mentioned she would call when the tickets were ready for pickup.

After sorting out the holiday, my mind turned to our next challenge, which promised to be the most demanding yet. I had recently joined a local gym where I worked out on Thursdays. I picked Oliver up afterward and spent two hours at the gym—mostly on the machines rather than lifting weights—followed by a session in the sauna and a quick shower.

On one occasion, while I was in the sauna wrapped in a towel, a man entered. I had noticed him a few times before without paying much attention, but now I took a closer look. He was well built, clearly benefiting from regular gym sessions. I’d guess he was in his mid-forties: tall, broad-shouldered, with a nicely defined chest and stomach, and neatly groomed with short hair. Catching me staring, he remarked on it, and I apologized, blushing like a teenager. We ended up chatting casually for a while before I invited him for a coffee at the gym’s café. Over half an hour, we got to know each other, he introduced himself as John, and I told him I was Carol.

He turned out to be a widower with two grown children, easy to converse with and very knowledgeable. Although he was actually fifty-two, I remarked that he didn’t look his age. I mentioned that I was married to a sailor and that we shared a house with another couple—though I conveniently left out just how much we shared. With a playful wink, he remarked that if he were thirty years younger, he’d be thrilled to be with me.

We said our goodbyes, and I even kissed him on the cheek. As I made my way to Sandra’s, I couldn’t stop thinking about his last comment—he seemed perfect for our upcoming challenge. That night, I detailed my day to Mikki, describing exactly what he was like, and she suggested that I should sound him out the next time I saw him.

The following Thursday, after finishing my workout, I headed towards the sauna and noticed John entering. To surprise him, I adjusted the towel around my waist. I gave my nipples a quick pinch to make them perk up, then walked into the sauna and sat across from him. He couldn’t help but stare at my breasts.

We were alone, and I decided to be completely honest about the challenge and our living situation. I didn't want him agreeing under false pretenses. After explaining everything, I apologized if I had offended him. He assured me that, on the contrary, he was quite flattered.

Looking into his eyes, I loosened the towel and spread my knees a bit, telling him, "John, this is what I'm offering you, and Mikki's on board too. To complete the challenge, you need to have sex with both of us." He stood up and asked if I wanted a coffee. I said I would love one, then secured my towel around me and went for a shower. Once dressed, I joined him at the café where he stood and extended his hand. Instead, I brushed it aside and gave him a light kiss, followed by a more passionate one.

As I sat down, he asked if I was serious about this. I confirmed, saying Mikki was serious too and that he would like her. He mentioned that seeing me naked in the sauna, he admired my body and would be foolish to refuse my offer. He suggested booking a table so we could all have a meal and chat first, and then, if we decided to proceed, we could go back to his place.

I agreed and asked if he was available next Saturday. He confirmed, saying he would reserve a table for 7:30 and provide further details the following Thursday. I asked for his address, mentioning that my husband would pick us up at midnight. After giving him another kiss, I said, "Until next week."

Later that evening, I informed Mikki that the plan was a go. We decided to tell the guys on Friday, giving them one more chance to say no. Without any issues, James drove Mikki and me to the restaurant stopping around the corner. I was a bundle of nerves and completely out of my comfort zone. Although I had been with other men before, it had always been with Bobbie—in a stranger’s house and with an older man. I couldn’t help but wonder if he'd even be able to get an erection. I asked Mikki if we should call it off and go home, but she replied that since we’d come this far, we should enjoy the meal; if either of us felt differently afterward, we could cancel.

That plan worked for us. We went inside, and John greeted us with a wave. I introduced him, and we both shared a kiss with him before sitting down. During the meal, all my doubts vanished as John charmed us with his witty stories, making us laugh. Once the meal ended, Mikki and I excused ourselves to visit the bathroom.

On our way back, Mikki confessed, “Look, Carol, I’m definitely up for this—he’s such a nice guy,” adding that she was incredibly turned on. I had to admit that I was feeling aroused too, and I was fully committed.

After leaving the car, I couldn’t help but notice that his house was huge and very inviting. Settling in the lounge, John offered us drinks, and we both chose white wine. After chatting for a while, I glanced at Mikki and said, “This isn’t really why we’re here.” Slowly, we began to undress each other, giving John a little show.

We then positioned ourselves on either side of him, exchanging kisses as he caressed our breasts. After a moment, he looked us over appreciatively, remarking that he was one lucky guy, before suggesting that we move to the bedroom.

Like the rest of the house, the bedroom was spacious and tastefully arranged around a large bed in the center. In a soft whisper, he admitted that he hadn’t been with anyone for over three years; his wife had been too ill and had passed away nearly two years ago.

As I kissed him, I hushed him, reassuring him to relax—we would look after him. Removing his jacket and shirt, Mikki admired his well-defined chest. Then, with him seated, we began by taking off one sock each, followed by unbuckling his belt and pulling his trousers down. I neatly folded his clothes and placed them on a chair, while Mikki and I pulled down his underwear, revealing an erect cock that playfully brushed against Mikki’s face.

I needn’t have worried about him not being aroused because, as we both saw, this was the biggest, thickest cock either of us had ever encountered—it made my usual ten-inch dildo seem insignificant. All of my earlier doubts evaporated; I wanted him inside me.

Kneeling with her mouth open, Mikki wrapped her hand around as much as she could, and I placed mine over hers. With our four hands encircling his cock, whose head still protruded, we started to stroke him slowly. I tenderly caressed his balls—perfectly proportioned to the rest of him—and then licked the tip, which felt warm and inviting, taking in a few inches. Soon, Mikki followed suit, and we took turns sucking his cock, gradually working inch by inch.

However, I couldn’t quite take the last two inches—this was the first cock I couldn’t completely engulf. Eyeing Mikki’s pussy alongside that impressive cock, I asked John if he had any lubricant. He mentioned that he only had Vaseline, so I requested he bring it over. I applied a generous amount, then told Mikki to lie back. From the bedside cabinet, John produced an unopened box of condoms and handed it to me.

I explained that if he really wanted to use them, he could, though we would prefer he not. Smiling, he told me to put them away. Although I didn’t want to pressure him, Mikki and I had agreed that any penetrative encounter should end with him coming inside us to complete the challenge.

John then positioned himself on top of Mikki—he looked enormous next to her. I guided his cock to her entrance and urged him to take it slow. He pushed the head in, paused briefly, and then, when I encouraged him to go a bit further, he did—pulling out slightly before reinserting deeper. Once he was fully inside, I asked how it felt. John replied that it was worth the wait, and Mikki added that it felt wonderful.

Mikki reached two climaxes before John, with a final thrust, groaned and announced his own. "Fill me up," Mikki cried out, and John complied as Mikki trembled with her last peak of pleasure. As John withdrew, I took his cock into my mouth, cleaning him.

I saw the evidence of their passion spilling from Mikki, so I began to lick and clean her as well. We then positioned ourselves in a sixty-nine, pleasuring each other orally until we both reached another climax. John watched us, amazed.

By the time we finished, John was hard again. I lay back, guiding his cock into me. He felt enormous, bigger than anything I'd felt before. We found our rhythm, and it felt incredible. I built up to a massive climax as he continued to thrust into me. With a shudder, I came, squirting all over him.

Undeterred, John continued to build speed. I was lost in the sensation, moaning incoherently. We both neared release as he pounded into me, moaning. He then stilled, pumping me full of cum and bringing me to another intense climax.

John lay on top of me, still inside me, as his cock slowly softened. Even then, it still looked huge. Mikki cleaned him up, and then me.

We showered and dressed. With half an hour left before Bobbi arrived, we sat in the lounge with a glass of wine, chatting. John expressed his gratitude, saying it was the best night of his life and that there were too many firsts to name. We thanked him, sharing that this was our best challenge so far, and told him about the others.

At twelve, we got up and, with a final kiss, left. Walking down the drive, we saw Bobbi waiting.

When we returned home, I headed straight to bed, holding Bobbie close throughout the night. In the morning, I made slow, passionate love to him, showing him that I was his. After breakfast, I needed to have a conversation with Bobbie. When I asked if he was alright, he assured me that nothing had changed. I thanked him for his support and mentioned that both Mikki and I had enjoyed our night. He kissed me, saying that as long as I was happy, safe, and continued to love him, he was content.

Mikki went to get Oliver while the guys headed to the club, and I started preparing the roast. Later, Mikki and I crossed off an item from our list: eight "be with a guy at least twice our age." I rolled a die and landed on two "being naked in a men’s changing room," which we both thought would be fun and enjoyable.

Mikki asked about the previous night, and I told her I loved it and was impressed by his size. She shared that when it emerged from his pants and hit her face, she was shocked. She added that once it was fully inside, she almost passed out from pleasure. I mentioned how much he came, thanks to his large balls.

We had dinner, played trains with Oliver, and put him to bed. Then, we set our paddles on the sofa arms, anticipating what was to come. That night, I went to sleep with a satisfied feeling my pussy from Bobbie's cock and a warm glow from the paddle.

Tuesday night at the local swimming baths featured an advanced adult swimming class, with two-thirds of the pool set aside for lessons and the remainder open for free laps—a perfect arrangement since it guaranteed an absence of children both in the pool and the changing rooms.

Mikki and I secured our clothes in a locker with our key banded around our ankles before changing into our modest one-piece bathing suits and heading to the pool. We swam lengths for about forty minutes before grabbing our towels and moving on to the changing rooms.

Intentionally, we entered the wrong changing room. Since it was empty, we took off our bathing suits, hung them along with our towels, and made our way to the showers, where, turning on the water, they were set out in a number of blocks, each with three showers.

We assumed we wouldn’t be seen, even though we had technically completed the challenge. Then we heard men’s voices. Soon enough, four naked guys entered the shower area, stopping short when they saw us.

Summoning all my courage, I asked what they thought they were doing in our changing room. They pointed out that it was indeed us who were in the wrong room. Mikki apologized, and they simply laughed. I replied that since we were already here and had been seen, we might as well finish.

The man standing between Mikki and me even lent us his shower gel.

After both of us had showered, we began drying off, only to see more men entering the changing room. Acting as though it were completely normal, we dried off with smiles, wrapped our towels around our bodies, and picked up our suits as we stepped out to claps and whistles—we noticed more than one man visibly aroused.

We then entered the women’s changing room to retrieve our clothes, quickly dressed, and left. I was pleased that the guys had taken our stunt in such good humor; it only added to the fun.

That night, true to our reputation as a mischievous duo, we served our punishment with warmed spanked bottoms—and then our guys hard cocks.

The following day, when we pulled out the list and dice, we crossed off “naked in a men’s changing room” as completed. Next, we rolled all four dice; after getting two challenges we’d already completed, we re-rolled until we ended up with a full house of twenty-four, revealing the challenge: “chat up a woman and have sex with her.” This one promised to be far tougher than the last!

That Saturday, the four of us decided to order pizza, and it was Mikki's turn to give the tip. We didn't bother putting on robes before answering the door, which turned out to be our first mistake. When we opened the door, a delivery guy we didn't recognise was there, staring at our naked bodies. Adding to our embarrassment, a couple on the path was also gawking.

We quickly grabbed coats to cover ourselves, while I took the pizza and Mikki paid the delivery guy. When she asked about the usual delivery guy, he explained that his wife had found out and forced him to quit. He then cheekily asked for his tip, and I told him that seeing us was his tip as I shut the door.

I felt a bit sorry for the other guy and his wife, but Mikki pointed out that he could have refused and said no. On the bright side, the pizza was still hot, unlike the last time.

After the pizza, Mikki and I undressed ourselves and then the guys. I sucked Bobbie’s cock while Mikki did the same for James. We then positioned ourselves on the couch, with James entering me from behind and Bobby doing the same to Mikki. As we established a steady rhythm, Mikki and I kissed, moaning into each other's mouths.

Mikki then called out "swap," and the guys switched places. Each one entered us again as we resumed kissing. I called out "swap" once more, and they switched back, building up a steady rhythm while we continued to kiss. James announced he was close, so I rubbed my clit and urged him to come. After a few more thrusts, he buried himself deep, filling me with his cum. With James still inside me, I kissed Mikki and rubbed her clit until both of them came.

Mikki and I then moved to the floor, positioning ourselves in a sixty-nine to lick each other clean and retrieve our guys' cum, bringing both of us to a nice climax. I then sucked James' cock clean, as Mikki did the same for Bobbie. Once they were both hard again, I said, "There you go, your fiancée is ready for bed." Mikki responded, "So is your husband."

We then went to bed and made love to our respective partners. The next day, we went to a club to watch strippers, followed by a Chinese takeaway. While eating, Mikki and I shared our next challenge with the guys. James suggested we were due for a girls' night, so the next weekend he and Bobbie would go to his mom's house to do some work.

James had decided not to sell the house he'd inherited and planned to eventually live there with Mikki. The house also had a separate granny flat on the side that hadn't been used in years. He wanted to fix it up in case Sandra wanted to join them. That night, I slept with James, and Mikki slept with Bobbie.

The following Friday, we showered, cleaning ourselves and giving each other an orgasm. Then, we dressed in short skirts and tiny tops with jackets over them. Underneath, we wore matching sets of bras and panties. We headed to a club popular among the gay crowd, thinking that if Friday didn't go our way, we could try again the next day. After grabbing a drink, we split up to mingle. The first woman I chatted with was very nice but straight and was there with a friend just enjoying the vibe.

The next woman I encountered was cute, but she had a girlfriend. I gave her a kiss and then went to find Mikki. She was having similar luck. As we sat down with our drinks, contemplating our next move, a tall blonde woman in a striking red dress approached, asking if she could join us.

We agreed and began talking. Her name was Helen; she was twenty-three and lived with her friend Beverly, who was the same age. Both were single, worked at a bank, and occasionally shared a bed. We shared details about our arrangement, which intrigued her, though she mentioned they didn't date men.

Helen had dated another woman for two years, but her partner had moved on from her and women, getting engaged to a man. While Mikki went to get another round of drinks, I asked Helen if she'd like to come back with us, noting that the guys were away. Helen was interested but only if Beverly was happy and could join us, and we agreed to have both of them over.

Helen mentioned their apartment was just a five-minute walk away and went to find Beverly. When Mikki returned with the drinks, I told her about Beverly, and she went to get another glass of wine. As Mikki brought the wine back, Helen returned with another stunning blonde, who sat down and joined our conversation. We all clicked well, and it was clear Helen and Beverly were closer than initially suggested.

I explained that we were just looking for a fun night and were open to trying anything between the four of us as couples or together. We assured them our partners knew about the evening, so there wouldn't be any issues. With that, Helen finished her drink and said, "Alright, ladies, let's take you home."

The apartment, situated above a high-end clothing store, was contemporary and brand new, offering a view of the river. It featured two double bedrooms and an open-concept kitchen, dining, and living area.

Helen grabbed a bottle of wine while Beverly took out four glasses. Beverly proposed that we'd be more at ease if we stripped down to our underwear. We sat, enjoying our wine and conversation. Helen mentioned that they were close friends but had decided not to pursue anything further. They had, however, discussed doing something like this evening several times before.

I shared with them about the list and tonight's challenge. Beverly expressed her enthusiasm to assist with our challenge. With that, she stood up and kissed Mikki. As Beverly pulled away, Mikki drew her back in, kissing her more intensely. I approached Helen, and we kissed, undressing each other while exploring each other's bodies.

Once we were naked, Helen gently pushed me back and began to perform oral sex on me, her tongue and lips sending waves of pleasure through my body. Her proficient movements, coupled with her steady rhythm, led me to my first orgasm swiftly. She persisted, gradually intensifying my arousal and inserting a finger, which elevated me to an even stronger climax.

Glancing at Mikki, I noticed she was just recovering from her own orgasm. Following that, we reciprocated, ensuring that both Helen and Beverly experienced two orgasms each.

They excused themselves and went to one of the bedrooms. When they returned, both were wearing strap-ons. Beverly looked at us, bouncing the faux member, and asked if we wanted to try. Helen then bent me over and slowly inserted the strap-on, easing it in until it was fully inside. She touched a button, and it began to vibrate, introducing a new and delightful sensation. I glanced at Mikki, who was smiling as she was being vigorously fucked. The toy inside me was doing its job, building me up to an intense climax.

Gradually, the sensation crept up on me, and with one final thrust, I experienced one of the most intense orgasms I’ve ever had. As I reveled in my climax, Helen shuddered and moaned, indicating her orgasm as she collapsed onto me. It felt unusual because the toy remained firm even after I had finished. When Helen withdrew, I sucked my juices off the plastic vibrator. She then moved over to Mikki, inserting the toy into her.

Beverly approached me and gently laid me on my back, working the strap-on into me. Although it felt the same as Helen's, the way she moved was different—not better or worse, just different. After we all reached a climax once more, they removed the strap-ons. Revealing the vibrating plugs inserted into their pussies, which had made them come. Mikki suggested we get one, and I agreed, saying it could be a Christmas gift for both of us.

Beverly took my hand and led me to her bedroom, both rooms had en-suites, with the beds looking over the river. As no one could see in there, there was no need to close the curtains, it was a lovely night with the starlight illuminating the room. We showered dried and climbed into bed, to thank her for fuckinging me so well I licked her pussy making her come.

Cuddling, we drifted off to sleep, waking a couple of times to make love. After another shower, we joined Helen and Beverly, for breakfast all sitting in the nude. Helen said that Beverly and her had talked, whilst it was for the challenge and one night of fun, they would both like to repeat it. Mikki nodded so I said we’d like that, would talk to our partners and get back to them.

After breakfast, Beverly ran us home to avoid the walk of shame.

After changing, we went to Sandra’s for coffee. She offered to keep Oliver until Monday so we could have a night together and join the guys on Sunday at the club.

Later, we retrieved the list and promptly checked off number twenty-four: "chat up a woman and have sex with her." We both chuckled, as we had gone beyond that with two gorgeous women, experiencing more than just a casual encounter. With the possibility of meeting them again, we decided to pause the challenges since Christmas was approaching and we'd be going on holiday soon.

That night, we enjoyed pizza and wine before heading to bed, where we spent the night making love.

On Sunday, the guys returned home, and we all went to watch the strippers at the club, followed by a Chinese meal. We recounted our Friday night escapades and how much fun we had, and they informed us that Sandra's apartment was now fully repaired and just needed decorating.

We also mentioned that Helen and Beverly had invited us back but clarified that they only dated women, so no swapping was possible. They were fine with us continuing the arrangement, and Mikki suggested that during our girls' weekends, we could get together again.

The guys noted that since it was just a girls' weekend, there was no need for any punishment. I couldn't decide whether to feel relieved or disappointed.

We informed them we were pausing the challenges because Christmas was nearly here and a holiday was coming up. They liked the plan, and James even suggested we avoid the dice during our holiday to prevent missing any unexpected opportunities. We all agreed that if an opportunity did arise, we’d discuss it as usual.

That night, when we went to bed with our partners, Bobbie said I seemed distant and asked what I was thinking about. I told him I’d enjoyed the last four challenges—it had been fun connecting with others. Then, lowering my gaze, I confessed that I was thinking about John and his impressive cock.

Bobbie remarked that both Mikki and I had enjoyed our time with him. I agreed, and when he implied that I wanted to see John again—acknowledging how well he knew me—I nodded, adding quietly that it would be okay as long as he was on board. Bobbie then asked if that one-time encounter would satisfy my desire, and I confirmed it would; I wasn’t looking for an ongoing arrangement, just a single night to explore some things I’d fantasised about. He encouraged me not to dwell on it if that was what I wanted, advising me to act soon, preferably before Christmas. He added that when I returned, I was expected to share all the details—and, that the “naughty Carol”paddle would get involved! I even pushed my luck by asking if I could stay overnight, and he agreed.

I mentioned I needed to ensure Mikki was comfortable with the idea and would discuss it with her the next day before making a final decision.

Later, I made love to Bobbie, riding his beautifully hard cock until he climaxed. I eagerly sucked him clean, giving him a blowjob he wouldn’t soon forget. As he filled my mouth, I swallowed every drop of his creamy cum, holding him tight so he’d feel the depth of my love and respect for my wonderful husband.

When Mikki came home from work, I told her about the conversation with Bobbie and asked for her opinion. She encouraged me—“go for it, enjoy it, and fill me in on every dirty detail”—and added it would be her turn to have both men all to herself for the night.

After my gym routine, I headed for the sauna, where I struck up a conversation with a couple in their late thirties. Soon, John arrived with a smile, greeting us with a cheerful “hi.” We chatted for a while until the couple decided they’d had enough and left.

Gazing at John, I deliberately removed my towel, letting it fall straight away to show him my body, and asked, “How would you like this for one night?” He smiled and asked how he could refuse such an offer.

Over coffee later, I explained my plan, and we agreed on Saturday night. I asked if I could stay over, and he welcomed the idea.

I mentioned that I didn’t feel like going out this time and asked if he needed me to bring any food. He assured me he’d take care of everything—just turn up at seven.

On Saturday, Mikki and I both took showers, then dressed in alluring lingerie sets paired with hold-ups. We completed our looks with knee-length dresses, tasteful jewelry, and vibrant makeup. Mikki was preparing for a night out that would end at home with some hard fucking by both our partners. Meanwhile, I was getting ready to enjoy an evening with my older gentleman companion with a huge cock.

I had three main objectives: to finally take his cock into my mouth and throat, to have his cock filling all three of my orifices, and to have as much of his cum both inside and on me.

James drove me to John's house and gave me a kiss, wishing me a good time. I reminded him to make the night special for Mikki.

John answered the door all dressed up in a suit and tie; he kissed me passionately and invited me in. Seated on the settee, John had an ice bucket filled with champagne and some little canapés. As he poured the champagne, I sampled one canapé—delicious—and asked if he’d made them. He explained that his wife was an excellent cook and had taught him.

After sharing a glass, I took hold of John’s hand, taking him to the bedroom. There, he had arranged scented candles with soft background lighting, and the covers were pulled back invitingly. I undressed him, carefully folding his clothes, and then disrobed myself while leaving my hold-up’s on, placing all my garments on a chair. I pushed him back and took his cock into my mouth, sucking and swirling my tongue up and down its length. Gradually, I worked it further until, upon reaching the back of my mouth, I extended my tongue to take it deeper into my throat.

Still unable to accommodate the final two inches, I grew frustrated and tried a technique I had read about. I lay on the bed with my head hanging off the end, creating a straighter path for deeper penetration. Looking up, I told him to slowly push his cock into my mouth, going deeper, and that I would slap his leg if he needed to pause.

Slowly, he advanced, withdrawing briefly so I could breathe. When I reached the spot I had managed to swallow before, he pushed an extra inch in; after a gentle leg slap from me, he paused. I slapped him again, and he pushed in once more, this time all the way—until I could feel his pubic hair on my lips and his balls resting on my chin.

After pulling off for a deep gulp of air, proud of my accomplishment, he remarked that no one had been able to do that before. I then instructed him to insert his cock again and gently fuck my mouth and throat. He complied, intermittently pulling out to let me breathe. When the ache set in, I slapped his leg twice, signalling him to pause, and then pulled away with tears in my eyes, spittle over his cock and across my face, overwhelmed with a sense of achievement.

Afterwards, I went to the bathroom, splashed cold water on my face, and dried my eyes. I returned with tissues to clean him up. Lying on my back once more, I told John that I needed his cock inside me and begged him to please fuck me now.

Getting on top, he began stroking his cock along my wet pussy, gently teasing me until he slowly pushed his length inside. The sensation was incredibly familiar, a slow, building rhythm that led to him gradually working his cock in until I felt him all the way. It felt just like last time, a steady, growing pace. Wanting to experiment with different positions, I asked him to pull out. On my hands and knees, I guided him back in, allowing him to penetrate even deeper in that stance. When he noticed the little jewel in my bum and asked about it, I coyly replied that he’d discover its purpose later.

In time, the pressure inside me built steadily until I couldn’t hold back any longer. With one steady thrust, I climaxed all over him. Once I had calmed down, I pushed him off, cleaned him up, and then took his cock into my mouth to ease the tension—I wasn’t ready for him to come just yet, as I had more positions in mind.

I rode him while facing him, then turned around and rode him again, each position delivering waves of pleasure. After getting off, I gave him a little suck before lying back down. As he thrust in again, I rubbed my clitoris until another huge orgasm overwhelmed me. John then resumed his steady rocking in and out of me. When I sensed he was close, I told him to pull out and finish in my mouth. As he did, he began to cum—just as I remembered from our last experience, though this time the amount was more than I anticipated, his first full load after I’d edged him.

I swallowed as much as I could, even though there was still more escaping down my cheek and dribbling onto my breasts. I licked him clean, then scooped up the excess and licked my finger, not wanting to waste a single drop.

From my overnight bag, I retrieved a long, loose T-shirt and slipped it on, while John changed into some shorts. We went to the kitchen for champagne and a snack he’d prepared. Everything was amazing, and after we finished, I took him back to bed.

This time, armed with proper lube, I pulled the butt plug out and placed it in the sink, then applied the lubricant to John’s cock. Once again on my hands and knees, I gazed at the impressive sight of his massive cock as it approached my puckered opening. This would be the largest I had ever taken. I instructed him to push slowly; as he slid in, he stretched me more than ever before. When he was fully inside, I felt completely filled. The burning sting subsided, replaced by a warmth unlike anything I’d ever experienced.

John moaned his approval, telling me it felt incredibly tight and wonderful. After we’d been fucking for a while, he grabbed my hips, pushing deep into my rear and releasing another load of cum that sparked an intense anal climax in me.

We then showered together, taking care to clean each other. I slowly stroked his cock even as it lay limp—it was still impressively huge. After grabbing some water, John and I went back to bed. Grateful, he confessed that it was the first time he’d had someone swallow his load and experience anal sex, and I told him I enjoyed it just as much.

With that, we drifted off to sleep, holding and kissing each other tenderly.

I woke up with John's impressive "pole" pressed against my back. After kissing him, I went down to perform oral, and soon enough his cock was rock hard. Lying on my back, he slid into me, filling me completely with his beautiful cock as we embraced in slow, unhurried lovemaking. Eventually, we both came, leaving me with a pussy full of his cum.

John then made breakfast, and we sat together, eating and chatting, thoroughly enjoying the morning and each other’s company. With still two hours left before Bobbie was due to pick me up, I asked John to take me back to bed. We stripped down and climbed into bed again, sharing kisses and cuddles, and after a while, I stroked him back to hardness with gentle strokes. I straddled him, slowly lowering myself onto his cock, riding him until I reached a delightful climax.

Afterward, I reclined and guided him as he entered me again. It felt perfectly right picking up the pace—I had one more spot that craved his cum. When he was ready, I told him to pull out and cover me, and he did exactly that, coating my pussy, belly, breasts, face, and even my hair. I always loved being covered in cum—from that very first bedsit encounter when Bobbie had come over my tits.

We then took a shower together; he washed my hair and meticulously cleaned every trace of his cum off me until I was shining. Under the cascade of running water, I knelt and took his cock in my mouth, bringing him back to hardness until, as a reward, he gave me one final mouthful of his creamy cum.

After drying off and dressing, I packed last night’s clothes along with the butt plug in my overnight bag, and then we settled in the lounge with our coffee. When the doorbell rang, John went to answer it and greeted Bobbie with a handshake. Offering him a cup of coffee, we all sat down, and I listened as the two men spoke about travel and sailing like old friends. Any onlooker would hardly believe that one was my loving husband and the other a man thirty years older—who had just spent the night fucking his wife. I found myself marveling once again at how caring and supportive Bobbie was, always in tune with what I wanted and giving me the freedom to enjoy it; in that moment, I fell in love with him all over again.

At the door, John kissed me and shook Bobbie’s hand, thanking him and remarking that he was a lucky man. I returned the kiss, correcting him by insisting that I was the lucky one. On the drive home, I recounted the night's adventures and our passionate encounters, teasing him by stroking his growing bulge while promising him that he would have to wait.

After parking the car outside the house and stashing my bag in the hallway, we walked hand in hand to the club to meet Mikki and James. Amidst the strippers, Mikki pulled me aside to get every detail, and later she recounted her own night, exclaiming how wonderful it had been. I knew exactly what she had experienced—having felt the same rush when Mikki was away on that overnight leadership course.

After Chinese takeaway Bobbie, with a stern demeanour, instructed me to retrieve "naughty Carol" from my room, I lowered my panties to my knees and bent over his lap. I received twelve firm spanks with the paddle on each cheek. As I was pulling my panties back up, Bobbie stopped me, saying not so fast. He reminded me that not only had I been out all night causing mischief, but I had also left poor Mikki to manage both men alone. He handed the paddle to Mikki, who accepted it with a smile.

I had only been spanked once by Katy, and this was Mikki’s first time. She instructed me to undress, and after disrobing herself, she sat down and directed me to lie across her lap. Gently stroking my sore bottom, she slipped a hand between my cheeks, fingering my pussy bringing me to a pleasant climax in a moment. She then administered six hard spanks on each side and followed up by soothing the area with cream. I kissed and thanked her, then took Bobbie to bed. As he made love to me, I expressed my love for him, assuring him that I would always love him and remain his.

The following week was Christmas, and Sandra would be staying with us for the duration. This time, she slept on the inflatable mattress in the lounge, with Oliver in his travel cot nearby. We enjoyed a pleasant meal on Christmas Eve and then headed to bed early. On Christmas morning, I woke up early and left Bobbie asleep, making coffee for Sandra and myself. We chatted while Oliver played, and I asked if she was doing alright. She responded with frustration, explaining that she had been lying awake, listening to Bobbie and me, as well as her daughter and James, having intimate moments. She admitted that she hadn’t been with a man since her husband passed away four years ago.

I had an idea—I’d bought something last month, so I wrapped it in Christmas paper and wrote a card that said, "Happy Christmas Sandra, have fun, love always, Carol xx." Later that day, when we had a moment alone, I gave her the gift, mentioning that it was a little something I wanted to give her privately. I told her that if she didn’t like it, she could simply return it, and I wouldn’t be upset.

Once we finished our coffee, Sandra and I put the turkey in the oven and started preparing the Christmas meal. Mikki and James arranged all of Oliver’s gifts in their bedroom. We all gathered around as he unwrapped his presents. This year was quite different from the last; Oliver was now walking and could say a few words like "da" for daddy, "muu" for mummy, and "be" for his bear. He also unwrapped his own gifts.

We retrieved our presents from beneath the tree and opened them, then toasted with some bubbly. Oliver was battling sleep, but we managed to get him settled down—otherwise he’d have been cranky later on. The day was fantastic; the meal went off without a hitch. Later that night, Bobbie and I made a bit of extra noise as we made love.

The next morning, as I sat at the table with two mugs of coffee, I noticed Sandra wearing a pleasant smile. She reached over, took my hand, and thanked me for the gift—she had clearly enjoyed the pink vibrator I’d given her!

On New Year’s Eve, while Sandra’s friend looked after Oliver, the four of us took Sandra out to the club. There was a comedian, a band performance, and a pleasant Buffet . I couldn’t help but watch Sandra, looking so happy as she enjoyed the night out with us. Suddenly, an idea struck me. I pulled Mikki aside and proposed matching her mum with John.

She thought it was a brilliant idea, and with a giggle she remarked that if they hit it off, John would end up with a sort of mother-and-daughter set, which made me smile too.

After the clock chimed and we joined in a round of “Auld Lang Syne,” we made our way home. Sandra took Oliver back to her house, while the rest of us returned to our place. A bit tipsy and laughing, I suggested to Mikki that we should ring in 1985 by “shagging each other’s partners.”

Without hesitation, Mikki stripped Bobbie down and took his cock in her mouth, while I did the same for James. Then, once everyone was undressed, Bobbie guided Mikki onto the settee and entered her pussy. Watching it all, I couldn’t help but think mischievously about Sandra lying in bed with her pink vibrator. We all eventually found a nice rhythm, and Mikki and I ended up with our pussies filled with cum.

Later, I took Bobbie to bed and made love to him as I listened to the sounds of Mikki and James in the room next door. With two loads of cum, I eventually drifted off to sleep on New Year’s morning.

That Thursday, after a workout at the gym and a quick flash in the sauna, John and I sat down for coffee. I shared everything about Sandra with him—explaining that, like him, she was widowed, financially independent, kind, and lovely woman. I told him I wanted to arrange a date, mentioning that Sandra was essentially Mikki grown up by twenty-two years. I assured John that I would set it up and advised him to let her take the lead, especially since it had been four years since she’d been with a man.

Two weeks later, after work, I was at Sandra’s to pick up Oliver. Over coffee, she sat with a silly grin—a grin I had about a month ago, the one sparked by the same huge cock. Sandra asked why I hadn’t warned her, and doing my best to appear innocent, I replied, “What, spoil the surprise?”

Mikki and I had completed eight challenges with sixteen to go. We enjoyed two new cocks and pussies. I’d loved these four challenges and my cock count was now seven, and my pussy count three.

If you liked this story, please like and favorite it. Your comments and suggestions are always appreciated.

The next story is about the holiday, where Mikki and I tackle more challenges from the list! Carol xx.