When One Thing Leads to Another Ch. 01

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What's a boy to do when his date eyes another man.
7k words
4.69
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Part 1 of the 5 part series

Updated 06/15/2023
Created 01/27/2023
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A trickle of light creeped into my field of vision and I instinctively tried to shut it out. So as quickly as they opened, my eyes tightly closed and I tried to fall back to sleep. I still felt complete exhaustion from the previous day and I could feel the soreness radiate all over my body. Also the bed felt so very comfortable this morning.

I had surprisingly woken up as a little spoon to Mckenzie, my hopefully soon to be girlfriend. My half awake head knew something was different as my neck and head lay in her shoulder but I couldn't put a finger on it in the moment. Instead my brain focused on the nice things, like why I felt so relaxed. My legs felt comfortably warm and sensitive. My boxer briefs were giving me a bit of a wedgie but it felt pleasant. And the sheet was caught up around my chest giving off an odd sense of security.

On top of all that I was so incredibly horny. I couldn't explain it but just the way my briefs were pushing up against my bottom felt so naughty. Not only that, but my cock was pressed up against her hip and the angle was making them feel even tighter.

I couldn't let Mckenzie know that was the true reason, all she needed to know was that I was rock hard and ready for morning sex. Eventually my aroused state overcame my tired state and decided it was time to make a move.

Well 'by make a move' I slowly began to move my cock up and down on her hip hoping that she'd wake up and we could have some morning sex and go back to sleep. I kept my eyes closed and gyrated my hips a little more. I felt like I was so close to getting off but I knew it would take more than just this thrusting.

Then all of a sudden. From above. a snicker. From a man.

And just like the light flooding my vision from earlier, the memories from last night came flashing by.

This obviously wasn't Mckenzie I was cuddled against. Everything was much too firm. This was a man laying on his back and I was curled up in his arm with my head on his chest. He flexed his arms to reposition my body so my entire groin was now pressed against him. I was too embarrassed to open my eyes and I shyly wiggled myself off his side but fell even deeper into his arm.

"You don't need to stop, just so you know" I heard the male voice above say.

My whole body was frozen. All frozen except my cock, which was still trying to slide up and down on anything in front of it. Somehow the revelations of last night made my dick even harder and there was nothing I could do. I finally realized the inevitable and slowly opened my eyes to the real world.

There laid Mckenzie. Just like me, she was curled up in the man's other arm with her head on his chest facing me. The way the sun was hitting her topless body would normally thrill me, but the way it was pressed up against another man made me blush. I hesitantly lifted my head and looked up at her.

Mckenzie was awake and watching me. we caught eyes and she smiled at me. "Oh my," she giggled "you just can't help yourself."

---The Previous Day---

We had checked into the hotel and began getting our things together in the lobby. I didn't know anyone involved in the wedding but I figured it was a big step that Mckenzie had invited me to be her date. We had been seeing each other for about a month now and this would be our first time away from our apartments in the city. It would also be the first time I'd be seeing her two roommates for a prolonged period of time. The two girls Mckenzie lived with, Lydia & Corrie, were also invited. Neither had plus ones.

Other than them, though, we knew no one. Mckenzie had known the bride from high school and she had ended up putting her in touch with the two girls that eventually became her roommates. Prior to this, I had only had spoken to the two roommates a handful of times. Both were career-first girls, both spoke their mind, and both seemed to have a new boytoy anytime I saw them. They gave mean girl energy.

Also, both seemed to be quite protective to Mckenzie. As a way to get to know them, a group of us were getting brunch together the following morning. Also as a way to get on good terms, I had agreed to drive them all back to the city from there.

As we stood in the elevator, I heard Mckenzie give a small gasp.

"Brad? Oh my god!"

She held the elevator open for the man and then jumped in his arms. I stood there confused for a moment as they embraced before Mckenzie turned to me.

"Its been so long! Brad and I were super close back in high school but then he went back home to London and we barely saw each other from there."

Mckenzie turned to Brad. "The girls said you might be coming but I didn't want to hold out too much hope."

I looked over at Brad. He stood over me by a few inches and yet was also significantly broader as well. He was dressed sharply but his ace in the hole was his British accent which I could tell was in some way already captivating Mckenzie.

"I have an early flight to catch tomorrow back home but I knew I could sneak one night in. Especially once I had heard you were coming." Brad stated as we hit our floor.

All 3 of us began getting off the elevator. "Great." I sarcastically thought. The last thing I needed was to compete against a jacked European guy who I'm pretty sure has had some type of history with Mckenzie. And not only that, he's on our floor. Thankfully he continued down the hallway to his room when we got to our door.

Our room was shaped as a typical hotel room. I mostly got ready near the beds while Mckenzie hogged the mirror. Finally after what seemed like an hour, she walked out and I had to stop and stare. Her hair and makeup looked absolutely amazing. Since her dress was laid out over the bed, she was only in her underwear.

I felt my dick stiffen up in my pants as I took her in. Her hair was up & curled in the back, showing off her beautiful neck. Her makeup was much bolder than usual and her red lipstick caught me by surprise. She hadn't worn lipstick since our first date. Either way, it dripped sexiness.

And all Mckenzie was wearing was the most 'fuck me' lingerie she owned. She was fully shaved around her black lacy panties. The small pink bows adorning them popped against the intricate black lace. She wore a matching black and pink lace bra. Although Mckenzie didn't have the biggest breasts, her fit stomach combined with the bra made what she had pop.

Below her lace panties were a set of sexy black stockings, which clung to her tight thighs. She grabbed her wine red dress from off the bed and slipped out over her head. The satin material hugged her body and showed off her fit figure. The skirt on the dress cut a little short, but the stockings were just high enough to cover the legs below. Just barely though. As she moved around the room, little flashes of skin from above her stockings would tease anyone watching close enough.

Although in our rush to leave I didn't have a chance to put on my tie, we grabbed our things and went off to the ceremony. I'd just put it on in a bathroom there. We arrived at the outdoor ceremony and made our way over to our seats. It was a little chillier than expected but fortunately only this part was outside. As things were still yet to begin, I made my way over to a mirror to work on my tie.

After a few failed attempts, I made something passable and walked back over to the seats.

And there was Brad. And Mckenzie. Again. And she was laughing about something. And she was wearing his suit jacket.

I quickly walked over to them but got no acknowledgment from either at first. I awkwardly stood quietly behind Brad as they recounted old high school pool party stories. Eventually Brad turned around and exclaimed

"Oh, didn't see you there! I hope you mind about the jacket. She said she was a little cold"

"Oh thanks for doing that." I said, quietly grumbling to myself why I didn't think to it first.

"I have to say though, what's going on with your tie?" Brad said laughing. "Here let me fix it. I have to do this with our intern in the office all the time."

"No, its ok." I mumbled but the decision had been made. Brad pulled off my jacket and in one fluid motion pulled me behind a chair. He moved up behind me and I felt his hands around my neck slowly undoing my tie.

At this point, I could see Lydia and Corrie point us out and began walking towards the three of us.

Corrie was wearing a tight champagne pink dress made of a shiny material. The dress went past her knees except for a slit on the one side that went high up her thigh. The dress emphasized her tan & toned legs. Lydia with her smaller stature was wearing a shoulderless purple dress with mesh sleeves and knee high dress shoes also showing off her wonderful curves.

They strolled over to see me being pushed up against a chair by another man while he forcibly adjusted my tie.

"Oooh what's going on here?" Corrie joked as Brad gripped my shoulders. I felt so small in his grasps as he adjusted my collar.

"Just some teamwork on his tie" Mckenzie answered as I could feel her look me up and down.

"I thought all men knew how to tie their own ties." Lydia loudly chirped. I blushed even though it was said in a joking manner.

"It's no problem at all." Brad responded. I could smell his cologne over my shoulders as he pulled my neck up.

"Besides, between my work life and my personal life, I get a lot of use out of them."

I saw Mckenzie blush as she got the double meaning. "Oh!" she squeaked.

"All done now." Brad smiled as he looked down at me. He immediately looked to Mckenzie. "Let's get a drink before the ceremony. Come with me."

She reactively giggled and exclaimed "Oh course." She then handed me her purse and simply said "Watch this while we're gone."

As they walked away, Corrie called out.

"Brad, don't forget your jacket," pointing at the chair

Mckenzie replied for him. 'Oh that's not his. His is keeping me warm right now."

I could see Lydia and Corrie smirking and whispering to each other as the two strolled away. I tried to play it off as normal but I was still just awkwardly standing there carrying Mckenzie's purse as she left with another man.

I quietly sat down next to them with the purse on my lap and waited for the ceremonies to begin. Time crept by as I eavesdropped on the two girls debate every guy they thought was hot and single. I guess when you looked like they did, you had your choice of anyone you'd want. Finally I saw Mckenzie & Brad came back right before it began. It sure it didn't seem like they had just one drink.

The rest of the evening did not go much better.

It started with Mckenzie adjusting the seats at our table so Brad could sit right next to us. He was already at our table but now he'd be right next to her. I spent much of the festivities just like prior to the ceremony, just sitting there holding her purse while the two of them hung out at the bar or the dance floor.

When I was finally able to dance a slow song with her I tried to lightly bring it up but it ended with her scolding me. "I see you every day, Brad's only here one night" I believe were her words. That argument ended with her in his arms again by the end of the song.

It was tough to make small talk when I was constantly looking over my shoulder. Brad acted nice enough to talk to but it was as nice as he could be given he was trying to fuck my date in front of me. I was thankful Corrie & Lydia were out dancing the whole time although I caught them giving some amused looks.

There was an after party in the hotel and at this point I was ready to throw in the white flag. Even though they had disappeared several times, I hadn't seen Mckenzie & Brad cross any firm lines. But I was tired of caring. Brad, you won.

As we walked to the after party I finally told her I was going to bed. I got a goodnight and a quick peck in return and I watched the two of them go in together with the rest of the party.

I keyed back into the dark room and laid down on the bed. I grabbed a weedpen in my bag and took a few hits, hoping that it would help me fall asleep. I didn't care at that point if and when Mckenzie came back.

"Urrrrg" I thought, "The brunch. And the drive home."

This was going to be so uncomfortable. Mckenzie, Lydia, & Corrie would obviously be there as well as a couple other girls (a few of which were at our table) from the party. I'd be the only guy, and the only guy whose date left him for another guy.

The two hour drive home with just the 3 girls is going to be excruciating too. Those girls talked about absolutely everything. It looked like both of them had found guys to go back to their rooms with too, so I knew to expect to hear details.

But on the other hand, I thought, so what? It'll be humiliating in the moment but then I'm out of this. I don't have to think about it again.

I laid there in the dark and finally began to drift off when from the hallway I hear noises.

A click on the handle.

A giggle.

Another click on the handle.

Finally, a buzz.

For a split second I though it was Mckenzie coming back alone. I figured if she and Brad did hook up, they'd simply go to his room. Unfortunately, I heard another set of feet enter the room.

"Are you awake?" Mckenzie asked a second before she turned on the light.

Between the effects of the pen and being half awake, I looked at the two of them in a daze. I gained consciousness and looked down to realize that I was still laying on top of the blankets. At least I was wearing a white t-shirt and boxer briefs.

Brad spoke up. "Hey, Mckenzie mentioned that you might have some weed. Do you mind if I get a rip?" He was still in his suit, except the tie was off and the shirt was unbuttoned at the top.

As I sat up and walked over to the bag to grab the pen, the two of them grabbed a mini bottle of champagne from the welcome bags and sat down on the bed. "There goes them coming and going." I thought.

As they passed the pen back and forth I began realizing how out of place I looked. They were still dressed sleekly and here I was, in a t-shirt and underwear. Mckenzie had her leg stretched outright showing off the sexy tops of her stockings.

Nobody said a word for a moment and I saw Mckenzie creep over to me. Without saying a word she began to forcibly kiss me. I felt her hands grope my butt up my back and she straddled me on the bed.

I was so confused in the moment but just decided to go with the flow. Thirty minutes prior I was visualizing being done with the entire relationship. But now? maybe I had won the whole time?

Brad, though, just sat there and watched. In fact he had even taken off his jacket and untucked his shirt. I looked over at Mckenzie with a confused expression.

"Baby are you ok if he stays?" she asked quietly.

It took a moment for me to process.

"He says he really into watching and one thing he was trying to convince me all day was if he could watch us this one time."

I began to understand and in a really weird way, this felt like a bonus? I had spent the whole evening assuming they were going to fuck and instead he's just asking to watch.

I nodded and Mckenzie began pulling off my shirt. We continued making out as I pulled her dress over her head. She looked amazing in her lingerie and stockings.

At this point I looked over and Brad had taken off his work shirt and only his undershirt remained. He looked at me as he pulled down his pants and when I said nothing, continued to take them off. Soon his socks and undershirt went and he was in his boxers as well.

Although it felt a little weird, I dawned on me that if he was going to watch us, he was probably going to want to jack himself off as well. I cringed a bit inside but reminded myself he was on a plane in the morning.

Mckenzie, though, could not keep her eyes off of him. Brad was very well built and his tight underwear showed off a well endowed shadow. As Mckenzie kissed me, I felt her pulling in his direction over and over again.

Eventually I was laying on my back next to Brad as Mckenzie sat on my legs and slowly began to slide down my boxers. To my point of view immediately on the left, I could see Brad pulling down his briefs as well.

Even before it was fully out I knew he was bigger and thicker than me. He wasn't huge but it was noticeably large. And it was just a couple feet from my face.

Mckenzie had slid my boxers off and slowly giving me a handjob. I was still semi hard at this point as she slowly glided her hands up and down. I saw her look up at Brad and the handjob stopped. She crawled up and began kissing me again while straddling my naked body.

"Baby....." she whispered in my ear "I completely understand if you don't want to but if maybe maybe maybe maybe you can think about it..."

I prepared for the worst.

"Would it be ok if Brad participated a little bit too?"

I began to blush. "Participate how?" I asked softly.

She whispered back, "I mean...you know..."

I understood. She wanted a threesome.

At this point, the night had been so long and stressful I still wanted some release. Yes, it would be a little weird but I wouldn't see him again. Also this still felt like a small win given my prior thoughts.

I slowly nodded my head.

Mckenzie gave a small squeal and began kissing me again. For a few minutes nothing was different and we continued kissing in the middle of the bed.

I could feel the bed move as Brad made his way towards us. We were both on our knees kissing when moved only inches away. He watched for a few more moments until I saw him slowly pull Mckenzie's face towards his.

She didn't hesitate and they began making out. I knew this was what I was getting myself into but it still caught me by surprise to see. I could tell she was enjoying it as he moved her around the bed effortlessly.

Just as I thought they were forgetting about me, Brad put arm around my waist and pulled me close.

"Show me how you go down on her." he commanded.

Mckenzie lay on her back in her lingerie. Her hair was slightly disheveled but this made her look even more sexy. I slowly pulled her panties to the side and began to lick. I soon heard her begin to moan. After a few more moments, Brad lightly pulled me back and began going down on her too. Her moans picked up but Brad began to slow down again.

"Go kiss her" he directed at me. We began making out again as he slowly goes down on her. I could feel Mckenzie shaking in my arms. Soon, though, Brad pulled her down and told her to give me a blowjob. There's something about Brad's directness that was almost relaxing. It made me feel a little submissive but it good someone knew what they were doing.

Mckenzie began blowing me as he watched. Maybe it was the drinks earlier in the night. Maybe it was the weirdness of the night, but I was still only semi-hard. Brad told her to stop and she curled up and began kissing my neck to loosen me up.

I closed my eyes and tried to relax. Soon I felt warmth on my cock again. I was being blown again. This time though was different. This one was rougher but also seemed to hit in all the right stops. And soon I was completely hard.

Mckenzie caught me looking down at Brad giving me a blowjob and I could feel her studying my reaction. My justification in the end was that it felt so unbelievably good. He played with the shaft. He played with the balls. He knew what he was doing.So I just went with it.

After a few more minutes, Brad aruptly stopped and began kissing Mckenzie. My cock could barely stand still. I was so horny now. I watched as the two began to move into a 69 position with Brad laying on his back with Mckenzie on top. She began to shudder as Brad used his tongue and fingers on her pussy as rested on her face.

I watched as slowly leaned over and began moving her face towards his cock. He was fully erect and only inches from her face. Mckenzie slowly put her mouth around the head and began bobbing her head. I thought I'd feel humiliated but in the moment I was so turned on watching. They continued to 69 until Mckenzie really began to moan. She arched her back and began to shake as Brad worked his mouth faster and faster.

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