Caught in Between

Ann, my beautiful Italian wife of nearly three years, and I made a point early on in our relationship of being open and honest with each other. That foundation has made for a marriage that we believe is truly special. Our agreement to be vulnerable with each other extends even to the bedroom, where we have had few qualms about sharing exactly what turns us on and then trying it out. However, some things remain secrets in every union. For the first couple years of our marriage, Ann and I had more than a couple sexual ideas buried in that territory.

Last fall, the shell that hid those remaining desires began to crack. The result was a threesome with Brittany, Ann's sister, that blew the lid off what I thought was the boundary of a healthy marriage. Several months later, I watched on in shock as my wife stripped naked at a party in front of a group of complete strangers. I didn't realize it right away, but it was that moment that changed the way I lusted for my wife in a wildly hot way.

It's not like my wife felt she needed to do these things to boost her confidence, either. Ann is a very intelligent, clever and friendly girl who is gorgeous by anyone's standards: dark Italian skin, hair and eyes with a beautiful complexion. She seriously looks far too young to be even in her mid-30s. She isn't oblivious to her beauty either and yet isn't conceited. Ann is indeed a rare breed and could have had any man she wanted. Don't ask what she's doing with me because I don't know that answer.

Anyway, even in the midst of those aforementioned activities, we did and still do hold marriage in high esteem, both ours and that of others. For example, I did not actually have sex with Brittany in the threesome since I didn't have her husband's blessing, and when a couple guys started to grope my wife during the strip tease, I decided to end it before it went too far. However, we mutually agreed that we could find different ways to have fun as long as it was for the purpose of pleasing each other and making sure no one was hurt, which meant being honest about our limits too.

As far as my fantasy goes, well, before I met Ann, the idea of a hot girl as the object of attention for multiple men was a severe turn on for me. However, I was understandably very possessive about Ann in particular, so she was the one woman I would never fantasize about in that way. I didn't want anyone touching her but me. However, when those men cheered her on as she unabashedly presented herself at that party, I didn't stop her. I didn't hate it. Instead, I was entirely aroused, and I made sure to tell her how much I liked her putting on a show for a group like she did.

Ann, sensing my excitement, revealed to me that it wasn't the first time she had stripped for a group of guys. I wasn't surprised, since I knew she was once a pretty wild girl before I met her. I then boldly asked her if they ever fucked her afterward. I wasn't sure I wanted to ask that question because I wasn't sure how I would feel about the answer. I figured I didn't really have anything to lose by asking. If watching her strip for a group was such an unexpected turn-on for me, maybe her being fucked by someone else wouldn't deter me as much as I previously thought it would.

Much more timidly, Ann disclosed that on two of those prior occasions she had been gangbanged. Not just fucked - gangbanged. She had never told me this part of her past because it had never come up and she figured I didn't need to know. She didn't tell me how many guys there were, and I didn't ask. I felt conflicting emotions about that revelation. I couldn't deny that, even to my surprise, the thought of my wife's taking multiple dicks was sexy as hell.

What I did want was to bring up the subject of double penetration because I personally thought it was the hottest sexual act. I had secretly fantasized about double-penetrating a girl for years before I met Ann. I don't think I would have carried it out prior to this point in my life, since I wasn't totally comfortable with being that close to another naked man, but it was hot to at least watch it. The more I thought about it, though, the more I realized that you don't have to be gay to double-dick a sexy girl, and no one was sexier to me than my wife, especially now.

Still, I had never shared this desire with Ann because I never imagined she would want to hear it. In the course of this conversation, though, I finally expressed to her that I really thought DP would be very hot and that for the first time since meeting Ann, I thought she would be the most worthy star of such an act. Once I finally let my mind entertain the thought of having my wife in a steamy sex sandwich, my lust ran wild, and the desire never left my head.

In the spirit of our newfound agreement to explore our sexuality within our marriage, we decided to pursue a threesome with another man and see if anything would become of it. Ann did admit her only concern was the anal penetration. To my knowledge at the time, neither of us had done it before and we imagined it could be awkward or uncomfortable. I was thrilled it was her only hang-up!

To her concern, we did try anal sex just a few weeks later, and we broke her ass in pretty well. Within the next couple weeks, she even ordered a butt plug to get a taste for DP, and she absolutely loved the feeling of her ass being stuffed while I fucked her pussy. We were both fully on board to try a male-female-male threesome as soon as one was feasible.

Not that it is integral to this story, but about a month later, Ann finally came clean and admitted her anxiety with anal had not been because she was an anal virgin but because she had indeed done anal sex with one of her ex-boyfriends and found it to be very painful. Admittedly, that disclosure was a small bump in the road for us, not because she had been fucked in the ass before but because of the dishonesty - which, like I said, was a very important part of our relationship. We moved past it pretty quickly though. It did explain a few personal things, and it also meant that Ann had that much more experience to guide us through our first threesome.

Anyway, even before the run with the butt plug, we had started looking for a third guy online. We were facing quite a tight rope, since we both were very happy with the life we had and didn't want to jeopardize it for one night of fun. We didn't necessarily need our family members or coworkers to know we had expanded our marital activities to include other individuals. Ann is a pretty popular girl, too, so if we weren't careful, there was a good chance she would be recognized. However we went about seeking out individuals to participate with us, we didn't want to be easily identified.

We had heard about Craigslist personal ads, but we found out that that section had been deactivated. After checking out other options, it turned out that a porn website yielded the best results. After posting a picture that Ann was comfortable with (provocative but no face or real nudity) and clearly communicating our intentions and the situation, we generated several inquiries that seemed legitimate (among a bunch of clowns, of course.) Within a couple weeks, we had it down to three serious candidates.

In the meantime, we talked about the details. We needed to establish boundaries as well as come with a plan, including a date. The plan came together in April, but we decided to set the date for July. There were a few reasons for this decision. For one, the weather would be nice, as we were still getting snow in April. Second, it would give us a couple months to make plans, including locking down a third person, securing a babysitter and making a hotel reservation. Third, we were planning to take some time off from work in early July, so we wouldn't have stress from our jobs interfering. Finally, July is my birthday month, so not only could this event serve as a sort of birthday present for me, but Ann typically does things for me or lets me do things to her as part of our lovemaking that she didn't always allow.

As for the events for that evening, we knew right away the location: the Hyatt hotel downtown. We didn't want to invite this third wheel to our house because our home where we live as a family wasn't the most appropriate setting for this raunchy session and, just in case something didn't go according to plan, we didn't want this guy knowing where we live. A hotel made the most sense, and we had always talked about taking a weekend downtown just to enjoy our own city. The Hyatt was as nice a hotel as the city had to offer, and we had gift cards for it.

It took a little longer to flesh out our boundaries. I, for example, didn't want the guy to get carried away with my wife. In fact, my initial condition was he could fuck her ass and nothing else, but it was going to be hard enough to find someone without the strict rules. We agreed he could not only eat Ann's pussy but also fuck her pussy from behind while I watched and then joined in. I wanted to make sure we drew a line between "fucking" and "lovemaking," so I pretty much didn't want the other guy making eye contact with her. At the end of the day, I knew I had nothing to worry about because I wasn't at all concerned that Ann was going to have eyes for anyone but me. I trusted her completely. I honestly think I could let 10 men bang her and she would never remotely desire to leave me for any of them. After all, this fantasy was mine as well.

Ann was a little less picky with the boundaries, since the third was a man and not a woman, so everything I was doing in the threesome was going to be to her. Her only real boundaries were that she didn't want someone else's dick in her mouth, which was fine with me, and she didn't want his cum on her. I wouldn't have minded seeing another load on her, but the guy would have to wear a condom anyway. We figured he could unload while in her ass, which would be enjoyable for him, even while wearing protection.

As May began, we locked down our third leg of the tripod. His name is Patrick. After I sent him a request on this website, he initiated the conversation by saying, "I would LOVE to be your third. Your wife looks like she NEEDS to be double penetrated, and I would love to help you make that happen!" He lived in the city, which was about a 20-minute drive from our suburban home. He was just what we were looking for: mid-30s, single, in decent shape and a cock that wasn't small but wasn't going to hurt Ann's ass. He and I chatted online at first and seemed to get along pretty well. It would be another month or so until Ann was ready to talk with him, but when she did, she liked him too.

Everything came together fairly quickly and much more smoothly than we expected. I don't think either one of us thought we would actually go through with it or to find someone to participate. Now that it was happening, it was, for me, at least, quite surreal. What had always been a secret and shameful fantasy of mine was now actually going to happen! It really set in around the second week of May when we made the reservation at the Hyatt for Friday, July 6 and told Patrick where to be and when. If he showed up, there would be no turning back. If he bailed, then it wasn't meant to be, and Ann and I would still have a fun night in the city.

The excitement built over the next couple months, and, even though we didn't actually talk about it much, I knew Ann was thinking about it more than she let on. In fact, a couple times I heard her quietly singing to herself, "One, two, three, not only you and me." It aroused me in such a way that I can't describe, to know that my precious wife was looking forward to being savagely shared before my next birthday.

Over the course of that time, we tried anal and made use of the plug on several occasions. By July 1, Ann said she was quite comfortable with it and was ready to try the real thing. With the night only a handful of days away, it was feeling as dreamlike as ever.

I didn't know Ann during her wild stage in life, but from period I have to work with, I can't imagine anyone currently suspecting her of being involved in such a debauched act as we were planning. She was too much of a consummate profession, loving family woman and moral example to be this borderline-crude sexual being. Actually, I'm positive that anyone without intimate knowledge of the inner workings of my own mind would not have imagined that I would be the one encouraging her, even making the proposition in the first place. I too was widely considered a straight-and-narrow kind of guy.

July 6 eventually came. Ann and I had been off work for a couple days at this point and we planned nothing for this Friday during the day. We ran a few errands, went for a walk and then got dressed and ready for the craziest night of our lives. I wore my black suit, and Ann wore a matching black dress that was as short and low-cut as she had in her modest wardrobe. I had taken her shopping over Memorial Day weekend to pick out that dress just for this occasion, so it was also her first time wearing it. With it, she wore a necklace, black high heels that were open-toe, and I even talked her into wearing an anklet on her right ankle, which to some people would signify that she was a married woman who had permission to have sex with other men, or so I am told. That meaning was not lost on Ann, and it was applicable to our situation in a very narrow context, but I had always thought it was a sexy look regardless. Ann was OK with it too because if anyone we knew saw us and noticed it, we could just as easily plead ignorance to its symbolism.

Once Ann was finished with her makeup and hair - which she had straightened and wore down, just the way I like it - we hopped in the car and dropped our child off at my parent's house. Then we went straight to the Hyatt to check in and drop off our belongings. After we took a moment to settle in, we set out to take a walk on this rather cool summer evening to a nearby restaurant at which we had a reservation. Before walking in, I texted Patrick to make we were still on. He texted back that he would just be waiting to hear from us.

We had a couple glasses of wine to go with dinner, then a small dessert before we asked for the check. It was a very simple but romantic dinner date without a mention of the depravity that was in store tonight. While we waited for the check, I texted Patrick to head to the end of the street where the restaurant was located. He said he would be there in five minutes, so we waited about that long before leaving our table.

Ann and I headed out into the comfortable summer air. By now, it was close to 9 o'clock, and the sun was all but gone. I looked to the right and saw the white SUV that matched Patrick's description of our stranger's vehicle. Until now, our only communication with him was exchanging electronic messages and some images. We couldn't have even been certain he was serious about his end of the agreement. Now it appeared to us that this scenario was very real.

Ann and I started down the street, nerves and excitement gripping my heart. The same two emotions caused my wife to giggle as her high heels clacked against the sidewalk. "I can't believe we're actually doing this!" she said softly but excitedly with a big grin on her face.

"I know!" was all I managed in response. We walked up to the SUV, and the window rolled down immediately. Surely enough, it was Patrick, the guy from the pictures.

"Need a ride?" he said with a smile. "Let me guess: the Hyatt down that way," he added as he motioned his head backward in the direction of our hotel. We officially introduced ourselves through the window, and then Ann and I got in the backseat. Once we were seated, Patrick turned the car back on, pulled out, busted a U-turn and made the short drive to the hotel. Pulling up to the front door, he dropped us off, and we gave him the room number, where we would directly head while he parked in a nearby lot.

Ann and I made our way up to our room on the fourth floor. We then turned on every single light in the room in order to have the best visual. Then we closed the blinds and curtains for the most privacy. Lastly, we quickly took turns to get ready in the bathroom. While Ann was in there, there came the knock at the door.

As Ann finished in the bathroom, I opened the door to none other than Patrick, whom I welcomed in. Before closing the door, I hung the "do not disturb" sign on the knob. Then, somewhat awkwardly, I explained to Patrick that Ann was finishing up in the bathroom and then we would move right on. For now, he had a seat in the room while I paced from my nervous energy.

The faucet shut off in the bathroom, followed by a couple clacks of Ann's heels on the bathroom floor until she touched down on the carpet. When she came around the wall into our sight, she was sporting a very naughty grin and the right strap on her dress already pushed down her shoulder. The visual combined with the anticipation had me hard immediately.

"Fuck," Patrick said, standing from his chair. "Godamn, you're even hotter than the pictures!"

Ann just smiled back shyly at Patrick and asked him to sit back down. "My husband here will let you know when it's your turn," she said seductively as she strutted over to me.

"You've never been hotter," I said to her as she took hold of my jacket and started to pull it off. I kissed her as we began to undress, as if oblivious to the onlooker. We were so psyched up that our new situation didn't slow us down at all. Ann quickly removed my coat, tie and shirt, all as we kissed throughout, and then playfully pushed me onto the bed. Then, still facing me, she pushed her dress all the way down, revealing her black strapless lace bra and matching thong. As she stepped out of the dress, she asked, "Keep these on, I assume?" referring to the high heels.

"And the jewelry," I answered. Ann knew full well how hot I thought it was when she wore high heels during sex. She did it only rarely - for my birthday, for example. Ann then crawled into the bed with me and began working on my pants, starting with the belt, then the button and finally the zipper before pulling the pants off altogether. Now we were both in our underwear while a practical stranger watched us.

Ann got on top of me, and we made out as our hands made their way around each other's bodies. Ann reached into my boxer briefs and grabbed my rock-hard dick, stroking it as her tongue explored my mouth. I responded by finding the clasp of her bra and unfastening it, causing the garment to fall off her chest and onto mine. Pushing the bra aside, I gave both of my wife's bare boobs a good squeeze as we continued to make out. Then my right hand made its way into Ann's thong.

Ann moaned into my mouth and beat me off faster once my finger slipped into her pussy, which was already quite moist. After a minute of being finger-fucked, my wife pulled away and slid down my body and removed my underwear. I was uneasy for just a second about being naked in front of this other man, but that slight discomfort went away as soon as Ann began to suck me off.

Running my hand through Ann's beautiful straight hair, I praised her as she held the base of my cock and slurped up and down the shaft. I helped her keep her hair out of her face as those gorgeous brown eyes looked up a me, her mouth full with my prick. She continued to blow me for a couple more minutes before we switched places.

With Ann now on her back, I slowly removed the thong, slipping it down to her ankles and carefully pulling it around her high heels. I tossed the garment aside as Ann lifted and spread her legs, just like she had for the rowdy group at that party several months earlier. Without hesitation, I dove in, holding my wife's thighs apart while my tongue went to work probing her sweet spot.