This is a story about reconnecting with my old friend Caroline. Believe it or not, we met at Sunday school when we were probably about four years old. Since the church was a huge part of our youth, we became good friends and spent most Sundays together, not to mention summer camp and all those other religious activities.
As we matured, and I use that term loosely, we began hanging out together outside of church. Two prim and proper religious girls began rebelling and turning into party girls. We used to go to parties and clubs together whenever we were in-between boyfriends.
Caroline was strikingly beautiful. She had the natural looks of a model. She was 5'8" tall with dark, thick hair and sky blue eyes. She had long, sexy legs and a great body. If that wasn't enough, she also had nice, full breasts. Every time we walked into a club, she would turn heads. Throughout the evening, there would always be a line-up of men at our table, as well as free drinks.
Caroline was fun, but on the conservative side. Unlike me, Caroline had plans for her life. Although everyone told her she should go into modelling, her lifelong dream was to become a flight attendant and see the world. She was focused and thus accomplished her goal. She even ended up living in Europe for several years. Although she could have had her pick of guys, she never settled.
Over the years, we went our separate ways. We both got married and didn't see each other as often as we should have, but we always kept in touch.
A few years back, we decided we would reconnect and vacation together with our husbands. Plans were made, and we went on a cruise together.
During that vacation, we had a lovely time. We all got along well. Her husband, Doug, is a lovely older man who happens to be wealthy. Caroline was always a smart cookie. With her good looks and hot body, she had no problem finding a rich older man. He treated her like a princess and gave her whatever she wanted. Caroline was living the well-to-do lifestyle.
During that cruise, there was a lot of flirting and teasing, but overall we all behaved. My husband made several comments to me about Caroline and how attractive she was. He couldn't resist pointing out that she had "spectacular" breasts—like I was blind and never noticed. I'm sure he would have jumped her in a heartbeat if he had the chance. I told him that Caroline was way out of his league.
My husband did comment that she was a trophy wife. This never occurred to me, but when I thought about it, I suppose she was.
About six months after that cruise, Caroline invited my husband and I to their condo in Florida for a winter vacation. Of course, we accepted, and off we went.
This vacation was more casual than the cruise, as it was their winter home. This time I noticed Caroline was a bit more flirty with my husband—she was hugging and touching him much more than on the first vacation. She wore sexier outfits and walked around the condo in a loose-fitting robe in the mornings. Believe me, I'm the master at teasing; I know when something's up, and I'm sure my husband was up.
My husband and Caroline turned out to both be early risers. They spent every morning together sipping coffee on the balcony before Doug and I woke up.
A few days into our visit, Caroline confided in me that her husband Doug had been pressuring her to spice things up sexually.
"Really, Caroline, you're one of the hottest women I know; what more could he want?" I was surprised by her confession.
"He wants me to have sex with other men," she bashfully revealed.
"He does?" The first thing that came to mind was that maybe he was impotent due to his age. I mean, he was pushing close to 70.
"Wow, does he want to watch?" I asked.
"Not really. He wants to have sex with other couples; he talks about it all the time."
"Oh...." So much for my impotency theory. Then the light bulb clicked—was this going where I thought it was?
"And... are you thinking about it?" I asked
"Well, he has always been very good to me, and I do like to please him." She sheepishly stated.
My husband's comment about her being a trophy wife came back to me. There is always a price to pay.
"My problem is I don't feel comfortable doing anything like that with strangers," she went on to say.
"Have you ever done anything like that?" Caroline asked.
"Well, not really. We have never exchanged partners, but my husband has had sex with a couple of my friends," I confessed, but quickly added, "But that was all approved by me; things kind of just happened."
"Oh, really?" Caroline sounded relieved.
I could see where this was going... "Caroline, are you asking me if we could switch partners?"
"Umm, yes," she giggled.
I couldn't help but giggle, too. It was just like when were kids talking about boys.
Wow, I wasn't expecting this. This entire conversation completely floored me. Although Caroline was always a fun party girl when we were younger, she never really had a wild side.
She went on to say that this all started with her husband after our cruise vacation six months earlier. Doug couldn't stop talking about me. He made it very clear that he was interested in me.
She asked me how I felt about it. I told her that her husband was a lovely man, and I would have no issues with it as long as she was positive this is what she wanted to do. I didn't want this to jeopardise our friendship.
She asked about my husband, and I just laughed.
"He has been singing your praises ever since the cruise. I know what he thinks."
So just like that, it was agreed that it would happen that evening. We decided not to tell our spouses but rather just surprise them. This gave both of us an opportunity to back out if we changed our minds or felt uncomfortable.
All afternoon, I had mixed emotions about this rendezvous. Although I have always been attracted to older men, and Doug was certainly older and very classy, I questioned his potency. I had never been with a man of his age.
On the other hand, I knew my husband would be thrilled with Caroline; what man wouldn't? I guess I was a bit jealous. Was I getting the short end of the stick?
I have always played the good wife and have been somewhat conservative in front of my husband, so this was out of character for me. It's one thing to have flings with strangers; it's completely different when friends and your husband are involved. Yes, I was apprehensive.
That evening, we all got dressed up and went out for a nice meal and a bit of dancing afterward. Caroline looked fantastic in a low-cut summer dress. Throughout the evening, my husband couldn't keep his eyes off Caroline's spectacular cleavage. I found his behaviour embarrassing and disrespectful of me, I kicked him numerous times under the table. The thought that he would be enjoying that cleavage later didn't help.
As the evening progressed, we were all feeling good from the alcohol and having a great time. Caroline grabbed my husband's hand and pulled him onto the dance floor. I can never get him to dance with me, but with Caroline, all of a sudden, he was a dancer.
This gave me time alone with Caroline's husband, Doug. He was a classy gentleman, very polite, and attractive. You know how I feel about mature men. We had a nice conversation.
Towards the end of the evening, I coaxed Doug up to the dance floor for a series of slow dances. As I glanced across the floor, I could see my husband and Caroline were all over each other. I have to admit, seeing them behave like that was uncomfortable. The thought that my husband would soon be having sex with Caroline was disturbing to me. Luck always seemed to follow him when it came to my friends. Caroline wouldn't be the first of my friends that he had sex with. (See other stories.)
Not to be outdone by Caroline and my husband on the dance floor, I moved much closer to Doug. I snuggled into his arms and sensually swayed my hips ever so slowly from side to side across his groin. I could feel his hardness pushing into me—oh, my, he was getting worked up. I whispered into his ear how nice it felt to be held. He held me even tighter, and his hands began to roam my body.
The alcohol was taking effect, and before the dance was over, I couldn't help accidentally grinding my pelvis into his groin. In turn, he grabbed my ass with both hands and pulled me closer, his hard cock pushing into me. "Oh Doug," I purred. He snuck a kiss on my neck.
By the time we all returned to the table, we were all sexually flustered. It was time to head back to the condo. Caroline and I made eye contact and confirmed we were still good with the plan. I bet she was, and I was still feeling a little bit annoyed knowing what was in store for my husband.
Back at the condo, I fell onto the couch next to my husband. Doug was sitting in a chair across from me and was admiring my exposed legs. My legs weren't as long as Caroline's, but just the same, they were shapely and thin.
Caroline came in with more drinks. I could tell she had loosened the top of her dress, and as she bent over to serve us drinks, she gave my husband an eyeful of cleavage. She then sat next to my husband on the couch, and a hand fell on his thigh. I could tell my husband was taken aback by how forward she was with me sitting next to him. Remember, the guys had no idea what we were planning.
My husband was sandwiched between me and Caroline and wasn't sure what to say or do. I saw him discreetly looking over at Caroline's long, crossed legs as she sat next to him. My legs all of a sudden felt inferior.
Doug got up to use the washroom, and Caroline used this opportunity to turn to my husband and began to run her hands over his shoulder. He was holding my hand on his thigh, and I noticed he was hard—very hard. I grabbed his crotch to feel his hard erection through his tenting pants. He sat up, obviously startled by my actions. He just looked at me with a confused look on his face. I was angry at his obvious arousal towards Caroline but managed to contain my anger.
"Oh my, honey, I bet this is for Caroline, isn't it?" I purred
He wasn't sure what to say. He's no fool; he didn't say anything. Caroline then proceeded to squeeze and assess his groin for herself.
That's when I asked him, "Would you like Caroline to take care of that for you tonight?"
He was shocked. He looked at me and then at Caroline. She gave him a devilish smile of approval. He was at a loss for words.
"It's fine, honey, go enjoy yourself. I'll take care of Doug," I reassured him.
He just nodded as Caroline stood up and took his hand to lead him off the couch.
At this point, I was history. I could have told him I was going to go fuck every guy in the bar, and he wouldn't have cared.
As Caroline led my husband like a puppy dog towards the bedroom, I yelled, "Have fun and see you in the morning, sweetie." The door to the bedroom closed.
When Doug returned from the washroom, he looked around and asked where the others were. I told him "they went to bed," he nodded, and then I said, "Together." His eyes just popped wide open as he realised what I meant.
"Does that mean we will have to share a room tonight?" he teased. "Umm, huh," I responded as I got up and grabbed his hand, and off we went.
As we passed the first bedroom, Doug slowed down to listen to the erotic sounds emanating through the closed door. His trophy wife, Caroline, was getting fucked by another man, just like he wanted.
