Weekend Foursome

My wife had to attend a conference for work last weekend and, since I didn't have any other plans, I decided to tag along. After all, the conference was about five hours away in another city and I had an old college friend who lived there. My wife also had an old college friend who lived there so we both figured it could be a nice getaway and we could visit our friends. Besides, the conference was in a nice hotel and it might give us the opportunity to have a little special time together. Little did I realize where that special time would lead to...

Friday night we pulled into town and checked in at the hotel. We reserved a double queen suite for the weekend and were very happy with it. After unloading our stuff in the room we each called our friends to come and join us for dinner. My friend Izzy was the first to arrive. She's a tall, thick, powerful woman I befriended in college. I hadn't seen her much in the previous ten years but I had followed some of her exploits on social media. Since college she had become quite the adventurous woman sexually. Despite her professional life as a bookkeeper, she had developed a desire for an active sex life, engaging with both men and women as the fancy struck her. My wife's friend Sam came along a short time later. Sam had lived quite the adventurous life as well. They first meet in college when Sam had previously been Susie. After college Sam finally got up the courage to come out as transgender and eventually started hormones and had top surgery. Back in college Sam had a crush on my wife and they had fooled around a couple of times but they never really pursued a romantic relationship.

Over dinner we all talked and had a great time. I was able to get caught up on what had been going on in Izzy's life since college. She had a four-year relationship with a man that ultimately didn't work out so she decided to move to a new town and start over. She was currently unattached but dating a few men and women casually. Sam had also recently returned to the town from having lived on the East Coast for a couple years. He had left the non-profit where he had been working and was now starting a new career in IT. He had been dating a new guy on and off for the past year but he was really reluctant to commit so Sam was still playing the field and enjoying himself. Izzy and Sam seemed to hit it off really well and we had a great time at dinner. By about 9:30 it was time to wrap it up for the night since my wife had an 8am meeting the next day. We said our good-byes and made plans to meet again the following night after the conference was done for the day.

I could tell my wife was feeling frisky when we got back to our room. Her hands were all over me as we prepared for bed. Eventually we settled into the plush bed and started running our hands over each other. During the course of our increasingly hot and heavy foreplay, she asked me a question:

"Do you think Izzy and Sam hit it off tonight? I could feel some definite sexual tension there."

"I think they did, but I don't know if there's anything sexual about it. They seemed to get along well. I could tell there was some tension between you and Sam, though. You know it would be OK with me if you two wanted to act on it. I know you haven't been with him since his transition."

"I have to admit; I've thought about that, and especially tonight. I think sex with Sam could be amazing; it could combine some of the strong masculinity that I love with some pussy that I also love."

After that last part my wife gave a very sexy laugh. She asked another question:

"And what about Izzy? Do you think she might like to join in? I wouldn't want to leave her out of anything fun."

"I'm pretty sure she would want to join in, even if only to be with you. I saw the way she was eyeing you and staring at your tits. I wouldn't blame her. After all, you know I love watching you with a female lover."

With that, I dropped my head down to my wife's tits and started sucking on her left nipple. Her head rolled back in ecstasy and she started moaning. I kept licking and sucking her nipple as she writhed in pleasure. Eventually I pulled my mouth off her nipple and said, "I think we're going to have a very fun night tomorrow night. I'll text Izzy in the morning and let her know that she should expect some adult fun. You text Sam and let him know the same."

"Oh God, tomorrow night is going to be epic! I can hardly wait!"

"Yes it will, my dear; yes it will."

My cock was so hard at that point I couldn't stand it any longer. I slid my hand down to my wife's pussy to check for lubrication. She was super wet. I knew the possibility of a foursome would get her sufficiently aroused. I pushed her back on the bed and started fingering her pussy to get her good and ready for my cock. Once she was ready I positioned myself so that I was right on top of her and slid it in. She was hot, wet, and ready and her pussy felt like a million bucks as it greedily slurped in my cock. I started pumping into her slowly at first and then built up a faster rhythm. Soon she was moaning and crying out for me to fuck her good and hard. I picked up the pace as much as I could and within a couple minutes I was cumming with ferocious force. She wasn't quite done yet so after I pulled out I laid down on the bed next to her and kissed her while I fingered her clit to a monster orgasm. We were both so spent that we fell asleep right there in the bed together without cleaning up.

The next morning I was able to sleep in while my wife was at her conference. During breakfast at the hotel restaurant I was surprised to find a text from Izzy:

Last night was fun. Tell me more about Sam.

The text conversation went on as follows:

What do you want to know? He's lived quite a life.

I'm more interested in some of the personal details. Is he seeing anyone?

He's got an irregular thing with a guy in town but he's not tied down. Why?

He intrigues me. Think he would swing my way a time or two? ;)

Maybe. He's mostly gay but has hooked up with women in the past. You interested?

I'd say I'm... intrigued. He raises a lot of interesting possibilities.

Today may be your lucky day. We could tell there was some interest from you last night so we're inviting both of you back tonight after dinner for some more intimate activities. Bring whatever you want; we're open for anything. Perhaps you can give Sam a try for yourself.

Sounds excellent. What time? What should I wear?

7:30 at our suite. Doesn't matter what you wear; we won't be dressed for long. ;)

My half of the plan was set. I was almost jittery with horny excitement the rest of the day just waiting to see what would happen that night. At 5pm I met my wife for the conference banquet in one of the hotel ballrooms. I told her about my text exchange with Izzy and asked her if she had spoken with Sam.

"I have, my darling, and Sam is plenty interested in fucking me, you, and Izzy tonight. Neither one of us will be disappointed."

"Damn! Now I wish we could skip this banquet and head straight up to our room. I'm ready for some action right now."

"Calm down, dear; you'll need to eat something so you have some stamina for the evening's activities. You'll be very much in demand tonight; but, I suspect you won't be the only one doing some fucking. Sam is bringing his strap-on to share with whomever's game."

"Well, this evening sure became a lot more interesting. I would have never guessed that about Sam."

"Oh yes. The testosterone shots make him a total horndog and his usual male partners like getting fucked so he went out and got the tool to do it."

"Good for him. I like someone who's always prepared."

We sat down and ate the bland, uninteresting conference banquet food. I swear, every single conference has the exact same food: chicken breast, red potatoes with rosemary, steamed broccoli, and a small square of carrot cake for dessert. Because of the length of the program we skipped out on the cake square and headed up to our suite. My wife put on a sexy bra and panties and her silk robe; I just stripped down to my boxer shorts and a t-shirt.

Right at 7:30 we heard a knock on the door. My wife answered and it was Izzy. She welcomed Izzy into the room and then pulled her in for a soft, sensual, long kiss. Izzy was somewhat surprised by it but her reaction told us that she was quite happy with the situation: "Wow, Dani, that's the nicest welcome I've ever had. I wouldn't mind another welcome and the rest of the tour, if you know what I mean." Izzy traced a line down my wife's chest and belly all the way to her crotch and then pulled her in for another long, passionate kiss. That was all it took for me to start getting aroused. My dick started to harden in my boxers. Just then there was another knock at the door.

My wife motioned to Izzy to sit on the other bed and said, "That's probably Sam. I'll let him in." She went over to the door and let Sam into the room. Meanwhile, Izzy sat down on the bed opposite me and shot me a sly smile.

"I hope you don't mind sharing your wife with me tonight. She's quite beautiful and it's been weeks since I've been with such a voluptuous woman."

"I'd almost be insulted if you didn't want me to share her, especially after that special welcome."

We both laughed about it and Izzy put her bag down on the floor next to the night stand. She was wearing a low-cut green satin top and tight skirt that clung to her thighs. She also had a black leather jacket. Her whole outfit told the story that she was primed and ready for sex. Meanwhile, my wife escorted Sam into the room. Sam was wearing a tight blue t-shirt with equally tight black jeans and a studded biker jacket with black boots. My wife made the obvious comment, "Wow, Sam; going a little hard in the butch direction tonight?"

"Fuck you, Dani! I just came from a bar with friends. I didn't have time to get dressed up in some bland, suburban shit like khakis and a polo shirt."

Just then, Izzy cut in with a comment, "Don't sweat it, Sam; I like what I see."

"And what's that, Izzy?"

"A strong, sexy man just waiting for some attention." Izzy got up from the bed, walked over to Sam, and pulled him in for a kiss. At first he was a little reluctant but eventually he gave in to Izzy's embrace. Sam dropped his backpack and leaned into the kiss more.

After he broke away, he said, "Damn, woman; for a chick you're a hot kisser."

Dani walked over to the two of them and put her hands on each of their shoulders and said, "That's more like it. I was hoping you two would get along." She let her hands trail down each of their backs and gave a playful swat on each of their asses.

Izzy took the lead at that point and invited both of them to strip down and join her on the bed. Sam threw his jacket down and peeled off his t-shirt to reveal his rock-hard chest and abs. Izzy unzipped her skirt and threw her jacket and top off revealing a lacy bra and panties underneath. Sam then sat on the bed, pulled off his boots, and unzipped his jeans. Soon the three of them fell into a pile of soft, warm, writhing sexuality. My wife was sucking on one of Izzy's nipples while Sam was sucking on the other. Izzy would purr and coo and make all kinds of wonderful noises indicating her lust was being satisfied. Eventually Sam slid a hand down to Izzy's panties and started softly rubbing her clit. That started Izzy getting even further buried in her own ecstasy. Soon, my wife pulled off of Izzy's nipple and started kissing her again while Sam was caressing her clit. Izzy was in absolute heaven with all the erotic attention she was getting. Eventually she started shaking and had a rollicking orgasm.

She laid her head back on the pillow and said, "Fuck! You two are amazing! I haven't cum like that in months! I owe both of you at least one tonight." Sam nodded in her general direction and then crawled over her to my wife. Sam laid on top of her and started kissing her which got my wife moaning in that special way that I love so much. Sam moved her hand down to my wife's pussy and started softly rubbing it just like he had done to Izzy. My wife was loving it but Sam stopped abruptly before it went too far.

"Dani, I brought something for you. And maybe for the rest of you, too, depending on how the night goes."

My wife stared at him with some puzzlement as he got off the bed. He reached into his backpack and pulled out another bag. Out of that bag he pulled an 8" strap-on dildo. He pulled off his boxer shorts and stepped into the harness. He walked over to the side of the bed and offered the plastic cock to my wife's mouth.

"Get it nice and slick with your saliva and then I'm going to fuck you like there's no tomorrow."

My wife almost squealed at the possibility and greedily started sucking on the strap-on to get it nice and slick. After a sloppy blow job on the dildo, Sam climbed on the bed and instructed my wife to get on all fours so he could fuck her from behind. My wife did so and then Sam started sliding the dildo into her warm, wet pussy. By that time Izzy was starting to come down from her orgasm and reached over and started playing with Dani's tits. Sam got down to some serious fucking while Izzy was working over my wife's tits. She was clearly ecstatic from all the stimuli going on at once. Sam settled into a serious rhythm fucking Dani while Izzy moved over to kiss her while Sam was fucking her from behind. Izzy moved her free hand down to my wife's clit to rub it while Sam kept plowing away into her pussy. It only took a few more minutes of that before my wife had a screaming orgasm. Once she came, Sam pulled the cock out of her pussy and laid down awkwardly across the foot of the bed. Dani collapsed onto her side next to Izzy while Izzy moved her kisses down to Dani's neck. Eventually Izzy rolled back over onto her back and they all laid there spent from their sexual exploits.

By that time my cock was so hard it had started to hurt. I was ready for some release. "Hey guys, remember me? I'm so hard I'm about to blow my load all over the place. Anyone want to help me out here?"

Sam sat up on the bed and said, "I could use a good cock. It's been a few days since my last good fucking.

I looked at him and said, "OK, stud, where would you like it, pussy or ass?"

He shot me a clever glance and said, "Wherever you put it, just make it nice and hard." He got up off the bed, slid the dildo harness off his muscular hips, and walked over to me.

I stood up, stripped down naked, and grabbed him by the arm and said, "Is your pussy wet enough for me?"

He responded, "Absolutely, but if you need more I brought lube. I always have lube in my backpack."

I slid a couple fingers into his pussy and could feel how wet and tight it was. That made me even harder. Izzy and my wife rolled onto their sides to watch the sight of me fucking a man pussy for the first time. I sat down on the edge of the bed and guided Sam down onto my lap facing me. He knew just what to do and guided my cock into his dripping wet pussy. I started bouncing him up and down on my lap as I grunted away. I was so horny by that time that I didn't last long at all before shooting all of my cum deep inside of him. I fell back on the bed completely spent. Sam got up off my softening cock and said, "You call that fucking? That was barely two minutes! I want more cock."

Izzy pushed herself up on her elbow and said, "Well, that could be arranged. You're not the only one who brought a special gift to the party tonight."

"No shit? You've got a strap-on, too?"

"Fuck yeah I do. I've used it on some of my female lovers—and some of my male ones as well."

"Well then get that bitch out and let's get busy. I want more cock."

Izzy stood up and grabbed her strap-on out of the bag. She stepped into the harness and snugged it up against her pubic bone for maximum thrust.

"Now get your ass over here and bend over this bed. I'll give you some cock!"

Sam did as requested and soon Izzy was slipping the dildo into Sam's already-fucked pussy. It slid right in easily. Izzy got into the rhythm of fucking Sam pretty quickly and started clawing at his back and slapping his ass. She made a monumental show of it and soon worked her way up to a frenzy. Just at that time, my wife got off her bed and came over to the bed the rest of us were on. She laid down on her back with her pussy right at Sam's face. Sam didn't need a hint to know that was his cue to start licking pussy. He gave my wife a ferocious tongue-lashing while Izzy was fucking him. Eventually my wife came to another powerful orgasm which was quickly followed by Sam's own orgasm. Izzy pulled the strap-on out of Sam's pussy with a slurp and then sat back down on the other bed.

By that point I had recovered enough and had seen enough hot action that I was ready to start again. I reached over to my wife and pulled her up in front of me. I started massaging her breasts and licking her left ear. That sent her into another state of utter ecstasy. She started squirming around and grinding her hips into my crotch which was getting my cock hard again. Eventually she turned around and moved her head down to my cock and started licking the shaft up and down. Sometimes she would swirl her tongue around the head of it. That action sent me into orbit with pleasure.

While she was licking my cock she slid a hand down to caress my balls. That hand soon headed further down and was caressing around my asshole. At one point she stopped, turned to Sam, and said, "Hey Sam, got that lube handy? I'm thinking I might need it—or, rather, my husband might." She got a lusty grin on her face and I knew what was about to happen. She was getting my ass ready for a good strap-on fucking. She knew that I enjoyed anal play and being fucked in the ass. Back in college I had experimented sexually with men and found it to be a lot of fun but I didn't really pursue any mansex after I got married. She always liked the idea of watching me get fucked and this would be the night she would see it.

Sam tossed her the tube of lube and she started spreading it on my asshole. My head was rolling in pleasure with each press of her finger into me. Eventually she had two fingers in my ass and I was squirming with pleasure. She pulled the fingers out of me and told me to flip over on my hands and knees, which I happily did. She then turned to Sam and said, "OK, Sam, time to man up. Grab that dildo because it's time for me to watch you fuck my husband."

Sam needed no more prompting. He grabbed his dildo, slid it on, fastened it, and climbed on the bed behind me. I looked back over my shoulder and said, "OK, Sam, make it good. I haven't been fucked like this in over ten years." Sam put the tip of the dildo right at my asshole and started to push in. The cock slid easily into my well-lubed and loosened hole. The feeling was of the cock sliding into my ass was so luxurious and indulgent that I couldn't help myself. I started rolling my head around and moaning in ecstasy. Sam knew what that meant and started fucking me in earnest. He started with long, slow strokes while I adjusted to the strap-on and then started picking up the pace once I was comfortable.

Meanwhile, my wife sat down on the other bed to enjoy the show. She loved the sight of her big, strong husband with another man behind him fucking his ass. She got so worked up about it that a hand found its way to one of her nipples and another to her pussy. Izzy, sensing my wife's enjoyment, leaned up behind her and started rubbing her tits and kissing her back while she watched Sam fuck my ass. I was in so much bliss from that fucking that I lost track of what Izzy and my wife did from there. All I knew from then on was that she was enjoying it by the sounds she made.