Surprise Threesome

Sam

After my slutty weekend, my thoughts kept returning to Friday night, my first group sex and bisexual experience with my friend Jenna. I realized I was curious to try more things with her and daydreamed about it that week during class. I turned myself on, imagining what else could happen, and what else I might want to try.

So, I decided to talk to Jenna about it. We both worked as lifeguards and swim instructors at the campus gym, so I planned to bring it up as I was taking over for her on a shift one night that week. In the end, I didn't have to go out of my way, as she ended up starting the conversation for me.

"So, you never told me what your married boyfriend thought about everything from last weekend. Did he enjoy hearing about our fun on Friday?"

"Oh yeah, big time," I laughed. "I think Mark was really bummed not to have been there."

"Oh really? What did he say?"

"Well... he was curious about what you and I had done together. I don't think I'd given him any sign that I might be interested in things with another girl before. I guess I'm not sure I really knew myself."

"Aww, well, I'm glad I got to pop your cherry, then. Sort of," Jenna flirted, bumping me with her hip.

"Yeah, sort of," I agreed, laughing and blushing. Then I pushed myself to take the conversation a step further. "And he was really curious about what else I might like to try."

"I have to admit I've been feeling pretty curious about that, too," she said, smiling.

I smiled back, my blush deepening. "I don't think there's much that I wouldn't be curious to try."

"Me either," Jenna answered, looking right at me.

The moment suddenly felt really intense, and I had to remind myself that we were at work, responsible for guarding the lives of swimmers. I could tell my throbbing pussy was going to be quite a distraction this shift.

"You'd want Mark to be there too, then?" she asked, drawing me out of my lust-induced haze.

"Yeah, if that would be okay with you."

"Sure. Do you think he would join us, or just watch?"

"I'm sure he'd want to join," I laughed.

"What would you want?"

"I think I'd be okay with that, but I guess I'm feeling a little unsure."

"Well, if it makes you feel any better, I'd mainly be there for you. Anything with him would be on your terms. Anyway, I'm sure I could find my own married guy if I ever wanted to. I know Mark is yours."

I laughed and brushed that off, but it made me feel a lot better to hear Jenna say that.

I knew it would be that much more exciting if Mark was there watching me with Jenna, and participating, too. Although the thought of anything happening between Mark and Jenna caused some prickles of jealousy, it also turned me on. I imagined that must be close to what he felt whenever he thought about or watched me with other guys. Maybe. But he always seemed to get really turned on by it, and I wasn't sure my enthusiasm matched his exactly.

Still, it was exciting to imagine Mark experiencing that, if Jenna and I were to share him. Having his "ultimate guy fantasy" of being with two girls at once. I knew I'd love to see how turned on he would be, and to feel like I gave that to him. I wanted to surprise him with it. And maybe part of it was that I still felt like I had some making up to do, for all the secrets I'd kept from him, with my neighbor, Chris.

Once I knew Jenna was on board, I just had to organize the logistics. It needed to be a situation when Mark would have a good amount of time, obviously. Not one of his quickie visits before or after work. I wanted to keep it a surprise, but I had to push him a little to make specific plans. Our meetings normally had to be pretty spontaneous, since Mark was always sneaking around. But for this, I would need to ensure Jenna was free and that we'd have privacy, ideally when my roommate Molly would be out.

Finally, Mark let me know that he'd found a time that could work. I saw his text as I was leaving my last class that Friday.

Mark: I think I convinced Heather to take the kids to her sister's for the night tomorrow ;)

My smile was instantaneous. I sent a message to Jenna right away.

Sam: Free tomorrow night for our experiment? ;)

Jenna: Of course ;-*

Jenna: Just tell me when and where

I replied with a thumbs up and then got back to Mark.

Sam: Okay :)

Sam: I have a surprise for you, so don't make any other plans

Mark: lol

Mark: Like what? Bowling?

Sam: Haha

Sam: I promise my surprise will be more fun than bowling :D

Mark: Mmm, I'm sure it will be

Mark: Can't wait

Then I just had to secure some privacy. My roommate Molly normally worked at the bar on the corner by our building Saturday nights, so our apartment could be an option. But she'd be home after 2:00am when her shift ended. I wasn't sure if Mark and Jenna and I would still be at it by 2, but I didn't want to have to rush to end things, just in case.

So, when I got home from campus, I looked around online for hotel rooms. Maybe I was making it too big of a thing, but I just felt like I wanted to plan something special to make it a nice evening and ensure we had privacy for whatever.

I ended up booking a room at Hotel Lincoln, an iconic hotel that was just a couple of blocks away from my apartment. I couldn't stop smiling as I clicked the button to reserve the room: 1 King Bed with a Lake View. Whatever happened, I figured it would at least be a nice treat to stay the night there.

***

I was bubbling with excitement throughout swim lessons Saturday morning. Jenna was working, too. She normally taught the Sunday morning lessons, but found someone to switch days so that she wouldn't have to go in early the next morning. As soon as I saw her, I filled her in on my plans, and she got excited with me. I could feel the tension building up between us all morning.

Then, when Mark arrived with his family for their lesson, he came over to say hi while Jenna and I were chatting again between classes. He was waiting at a distance for me to make an excuse to finish my conversation, not realizing that the girl I was talking to was Jenna. They hadn't met yet. So, after double checking that Mark's wife Heather was well out of earshot, I introduced them.

"Jenna, this is Mark. Mark, this is my friend Jenna that I was telling you about," I said, smirking.

Mark's eyes went a little wide as he approached. "Nice to meet you Jenna. I don't believe I've seen you around before. I know I would've remembered."

She laughed a little, blushing and eating up his flirting. "Yeah, I normally teach Sunday mornings, but Sam told me that all the hot dads come on Saturdays, so I had to check it out for myself."

Mark smirked at me, and I had to bite my lip to keep my smile from taking over my entire face. "Seems like Sam has good taste all around," he said.

"Yeah, and she tastes great, too."

My eyes widened when Jenna said that and I swatted her arm, shushing her as I blushed and looked around to make sure no one had overheard that.

She just smirked back at me and continued flirting with Mark. "I guess you already know that, though."

Then, one of the other instructors shouted over the noise of all the kids playing and parents chatting to start the next lesson, and I was saved.

During the class, Mark made his way over to me again at a moment where I was standing off on my own, observing.

"I can't wait to see you with her," he said, giving me a quick smile and a wink before anyone could notice.

I felt a tingle between my legs and smiled back. "You might not have to wait very long."

Mark raised an eyebrow as if to ask if I meant what he thought I meant. "Tonight?"

Rather than answering, I just smirked and moved on, giving instructions to a group of parents for the next part of the class. Between teasing Mark and witnessing his flirting with Jenna, I felt even more excited for the night to come.

***

After swim lessons, I stayed on campus to meet up with some classmates for lunch and to work on a final group project for the school year. Then I walked home to my apartment to shower and get ready for the night.

I spent far too much time overthinking what to wear and pack. Especially considering I was only going for the night, and the hotel was just down the street. Besides, if all went well, I would hopefully end up spending most of the night not wearing anything, anyway.

In the end, I settled on wearing a matching black lacy bra and panties under some cute patterned shorts and a fairly low-cut sleeveless top. I left my hair down and let it dry wavy after my shower, and put on just a little makeup. Then I packed a small bag with toiletries and a change of clothes for the morning, and debated whether to pack any of my toys. It kind of felt like too much, but I could imagine some scenarios in which it might be fun to have them. So, I brought a couple just in case.

It was almost 5:00 by the time I was ready to head out, and I made my way over to check in at the hotel, smiling and tingling the whole way. I'd arranged for Jenna to meet me there at 5:30. Mark still didn't know what the plans were, but I texted him to tease him a little more.

Sam: Can't wait to see you ;)

Sam: Hope you're excited for your surprise

Mark: I'm tingling in anticipation, as I hope you are, too

Sam: lol

Sam: Yes, lots of tingling :D

Mark: Good

Mark: I'm headed out soon

Mark: Am I going to your place?

Sam: You can park by my place, yes ;)

Mark: lol

Mark: Okay, I'll let you know when I'm there and await further instructions :)

Sam: Sounds good :)

After checking in at the front desk, I took the elevator up to the room on the twelfth floor. There was a huge king bed and a great view of the park and lake, as advertised. There was also a seating area with a couch and cushioned chair facing the TV, and a nice bathroom with a huge shower and a spa tub. I set my bag down and took it all in, opening the curtains all the way to get the most of the view and the late afternoon sunlight.

It was nice to have a few minutes alone in the room as I waited for Jenna to arrive. I checked in with myself and noticed that I was feeling much less nervous and more excited than expected. In some ways, it felt like the more wild things I did, the more normal it felt. Whether that was a good thing was yet to be seen.

When Jenna got to the hotel, I told her the room number so she could come up to drop her stuff off, too.

"I brought my stuff to stay the night just in case, but it's totally okay if you and Mark want to be alone later," Jenna offered, setting down her bag next to mine.

"Oh," I said, realizing I hadn't really thought through the end of the night portion. I had pictured spending the night with Mark and having the chance to talk about everything after, but I wasn't necessarily opposed to Jenna staying, too.

She seemed to notice that she'd caught me off guard. "We can play it by ear," she said with a wink and a smile.

I smiled back and agreed.

Then we went up to the rooftop bar to get some appetizers and drinks. It was a beautiful, warm, sunny day. We ordered some drinks and got lucky with a table right near the edge of the rooftop, with the best view and comfy couch seats. We chatted about work, classes, and our upcoming summer break, sort of dancing around any sexual topics at first.

But then, as we finished our first drinks and moved onto round two, Jenna dug deeper.

"So tell me more about Mark. How did that start? Did he come onto you at swim lessons or something?"

I felt my cheeks heating up at the mention of Mark, and bit my lip to keep from smiling too much.

"We actually met for the first time at the Shamrock Shuffle in March," I said, shrugging. "We talked a little, and I thought he was cute, but we didn't exchange names or numbers or anything. Then I ran into him again one night when I was out with some friends in Wrigleyville, and things sort of picked up from there."

"Did you already know he was married?"

My flush deepened, and I looked down as I answered, "I found out that night at the bar. He was there with his wife. But I guess... I don't know. Somehow it felt like it was already too late to stop it."

Jenna smirked knowingly. "That good, huh?"

I just laughed. "Well, maybe you'll get to find out."

"Yeah, maybe," she agreed, laughing too.

Then I had a sudden flash of self-consciousness, wondering what Jenna might think of me, now that she knew about Mark. "Do you think I'm a horrible person?"

She smiled back at me as she took a sip of her drink, shaking her head just slightly to avoid spilling. "Not at all," she answered once she'd swallowed. "His wife might. But no judgment from me."

I snorted a little. "Yeah."

"Pretty ballsy to have them both in your swim class, though! I can imagine that being really arousing or really stressful. Or both."

I smiled and bit my lip again, nodding slowly as I took another sip of my drink. "It's mostly fun."

We both laughed and kept drinking and talking.

Soon my phone chimed with another text from Mark.

Mark: Just parked by your building

Mark: Should I come up?

"He's about here," I told Jenna, smiling and texting him back, feeling a tingle between my legs.

Sam: No, walk down Lincoln to Clark

Sam: We're at the rooftop bar at the Lincoln Hotel ;)

I didn't tell him yet that I'd gotten a room, deciding to let the surprise slowly unfold.

Mark: We? ;)

I giggled and typed out a response, leaning in towards Jenna so she could read along.

Sam: Yep ;)

"He doesn't know how lucky he's about to get, does he?" Jenna asked, resting her hand lightly on my leg, just above my knee.

I felt another tingle shoot straight up my leg to my pussy as her fingers brushed over my bare skin. My throat felt dry suddenly, despite how well-lubricated I was from the drinks.

"I think he might have some idea after this morning," I smiled, blushing and biting my lip as I realized how close our faces were.

"True," Jenna agreed, smiling back.

I suddenly had the urge to kiss her, and couldn't think of a good reason not to go for it. So, I leaned in just slightly further, testing the waters to see if she'd meet my advance.

Jenna moved in too, licking her lip and smiling, leaving the last inch to me.

I took it, brushing my lips over hers lightly at first, gently pinching her bottom lip between mine.

She kissed me back softly, and it continued from there, neither of us pulling back. She cupped my cheek with her hand and brushed my hair back behind my ear. It was a delicate gesture, and not at all what I was accustomed to.

I realized how different it felt to kiss a girl. Her lips were soft and tasted like berry chapstick and rum. There was less urgency; no rush towards a specific end goal. The longer the kiss went on, the more I felt like I wanted to continue and explore.

"Can I get you ladies anything else?" I heard our server ask, interrupting us.

I pulled back quickly and nervously with a flush of embarrassment as I looked down at my drink. Both of our cocktails were still half-full, but that didn't stop me from ordering another round on our behalf.

Once the server moved along, Jenna and I looked at each other and laughed. I scooted away and took another, bigger gulp of my drink.

Mark arrived just as we were getting our next drinks. I watched him as he made his way to us, looking around at the other patrons, likely checking for anyone he might recognize. The risk of meeting up with your mistress in a public place.

Then he met my eyes and smiled as he approached. I got up to give him a quick hug, being careful to ensure it could pass as friendly. Mark gave Jenna a little wave and ordered a drink before the server got away.

"Nice view," he commented, relaxing back into the couch seat and looking around.

"Was that meant as a compliment for your present company, or the scenery?" Jenna flirted.

Mark laughed, his eyes lingering as he checked her out. "Definitely the company."

We talked and drank and flirted some more, and I was pleasantly surprised to notice that the vibe between the three of us felt easy and comfortable. I think Mark and Jenna were each flirty enough to make it that way.

The sun was setting as we continued to talk and eat and drink. Mark put his hand on my leg at some point, starting by casually resting it atop my thigh, then gradually sliding it down between my legs, tugging them apart slightly.

I flushed and squirmed as I felt his fingers brush over my inner thigh, near the hem of my shorts. Looking at Jenna, I noticed her eyes kept slipping down to watch his progress.

"So, what else is on the agenda for tonight?" Mark asked, pressing further up between my legs.

Jenna and I looked at each other and smiled.

Even though I was quite sure we all knew where things were leading, as the organizer, I felt a certain responsibility to get the ball rolling, so to speak.

"I guess there isn't a very detailed, outlined plan," I started, turning towards Mark and leaning in until my lips were brushing his ear. "But I got us a room downstairs. I want you to watch me and Jenna together. And whatever else you might want."

He tensed up next to me. I could feel his fingers digging into my thigh. When I looked down at his lap, the outline of his erection was clearly visible through his shorts.

"Does that sound okay?" I teased, smirking at him, then looking back to Jenna.

"Sounds like a perfect plan to me," Mark smiled. "Why don't I order us a bottle of something to bring to the room?"

So Mark got the server's attention and ordered a whole bottle of tequila for us to take downstairs.

I laughed when I heard him order. "I don't think we need that much encouragement to take our clothes off."

"Better safe than sorry," he replied with a wink.

I bit my lip and blushed, turning back to Jenna, who scooted up closer to me on my other side.

"I bet that tequila would taste great on your skin," she said, smiling back at me and leaning in, kissing her way up my shoulder to my neck.

I shivered and sighed when I felt her lips on me, and squirmed in my seat when her hand met Mark's between my legs. Suddenly, they were both rubbing and touching me, and it was intense. Mark took Jenna's hand and pushed it up higher until she was cupping my pussy through my shorts. They were each kissing one side of my neck, and Mark whispered into my ear.

"I can't wait to see her going down on you. I'm so hard right now. You're so sexy, Sam. It's so hot that you want to try this."

I couldn't help moaning as I felt what they were both doing to me. But I hadn't had enough to drink to lose my self-consciousness completely. This really wasn't that kind of bar. It was not a club by any means, there was no dance floor. Just people at tables or in booths, sitting around and talking, enjoying the evening air and some upbeat music. So I knew we were doing too much and probably making some people uncomfortable. But it was really hard to motivate myself to stop them.

"Maybe let's save it for the hotel room," I said, finally finding the resolve to push back on both of them.

"Where the fuck is that server?" Mark grumbled impatiently.

I laughed at him. "I'm surprised you're not suggesting that we should invite her along."

"I never said that," he smirked. "We could always ask her what time she gets off."

I just shook my head, smiling at his ridiculousness.

She returned with our tequila soon, and we got up to go.

There were others heading down, so the elevator ride was just secret looks, suppressed laughter, and awkward small talk.

Jenna pulled off her shirt as soon as we'd stepped off the elevator on the twelfth floor, revealing a pale pink bra, which I'd estimate was a C cup. She took that off too, and then she was standing in the hallway topless.