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In the days that followed my threesome of sorts with Summer and Maddie, I was worried that things would somehow change between Summer and me. They didn’t, and somehow that became the problem eventually anyway.
Summer was getting ready for law school, and knowing what a time commitment that was going to be she was making the best of her last days of carefree living. She went out more often than usual, sometimes on her own and sometimes with Maddie. She also brought home a lot of guys…sometimes on her own and sometimes with Maddie.
It’s hard to describe my relationship with Maddie. Everything we did brought us closer together, yet I still felt a distance between us that couldn’t be bridged. Not that I ever wanted more from Maddie, but she had a coldness about her that made it hard to feel close to her. Summer was ok with me going down on Maddie, especially after she’d been fucked. I was slightly uncomfortable with that, but I did it because I thought it was something Summer wanted me to do. They’d gotten pretty close, and by extension wanted me to get closer to Maddie too.
It wasn’t always the same, but for a couple of months we got into a routine where they’d go out, bring a couple of men back to our condo, fuck them for an hour or two, and when they were gone I’d help the girls unwind by going down on them, often as they’d have a drink and talk about their night. It made me feel included and like a third wheel at the same.
What worried me was that in the back of my mind, I knew that Maddie treated her exboyfriend Trevor more like a slave than a partner and I was afraid she was trying to influence Summer into moving our relationship in that direction. As it turns out, Summer had something else entirely different kicking around in her head, and one night as we cuddled in bed after she’d just been fucked by two guys, she let it out.
“How often do you think about the future?”
That’s not the kind of question you expect to hear while you’re laying on sheets dampened by another man’s sweat, coming from a girl who had cum that isn’t yours stuck in her hair.
“I don’t know. A normal amount of time, I guess?”
“I mean with us. Where do you see things going?”
A little panic set in. I thought that she was about to dump me. “You’re happy, aren’t you?”
“I am, and that’s what’s got me thinking about the future. I’m going to law school in a month. That’s going to be my life for the next few years. After graduation, then it’s career time and all that.”
“And by ‘all that’ you mean…” Neither of us wanted to say it, but we’d suddenly found ourselves in the marriage conversation.
“Yeah. We’ll be pushing thirty soon. I want to know where your head is at.”
I knew I wanted to be with Summer forever, but I’d never had any practical thoughts about what marriage would look like for us. Ideas like getting a house, saving for retirement, and all the things adults try to do still seemed far away. I was working a shitty job that wasn’t going anywhere, but I didn’t need it to go anywhere when we were living how we were. I realized that Summer was worried about my lack of ambition and having doubts about what kind of a husband I’d make. Meanwhile, it seemed like she had her future mapped out – at least as far as school and her career went – and was trying to figure out how I fit into it. I think she knew that finding another guy who would let her live how she wanted to would be hard, and weighing that against marrying someone content to work a deadend job.
“I don’t know. I know that I want to be with you but like…” I trailed off.
“How does this work? I’m happy now, I love you and what we do, but like in four, five years? Like straight up, there’s not going to be a time where I don’t want to fuck black guys. Are you going to be ok with that for the rest of your life?”
“I think so. It’s all I’ve known. After Melissa, I tried to have normal relationships and nothing ever worked out. Then I found you, and everything felt right again. This is who I am.”
“Ok,” she said, with obvious doubt in her tone. “I see a path for me.” I immediately noticed she said ‘me’ and not ‘us’. “My shortterm is crystal clear. school, then career. After that…I have thoughts but nothing feels certain. Should we get married?”
The word ‘married’ hung in the air for a few moments. One of us finally said it.
“Is that what you want?” I asked.
“I don’t know. Maybe? If not, then what?”
That question went unanswered. We didn’t resolve anything more that night, but realizing that Summer was thinking about these things forced me to do some of my thinking of my own. I wanted to be with her, that’s all I knew. Nothing changed after that night but Summer putting the question out there lingered over the next few months.
One night a couple of weeks later Summer came home, alone, from a club and she was grinning from ear to ear. She was excited and had something she was dying to tell me.
“Guess what babe?” She was drunk and still in party mode, so everything she said seemed over the top.
“What?”
“I’m going to Jamaica!” she shouted and hugged me as she said it.
“What do you mean?” I was confused.
“Tonight at the club, Daniella and I won a trip for two to Jamaica!” Summer was still overflowing with excitement.
I wasn’t sure what I was expecting, but it wasn’t that. I hadn’t met Daniella at this point, but she was part of the snow bunny crew of white girls that Summer and Maddie hung out with when they did the rounds at all the black clubs in town. I was happy for her, but it was clear that my sober energy wasn’t matching with Summer’s drunken energy and she misread me completely.
“You’re sure it’s legit?”
“For fucks sake, yes, it’s legit. The night was sponsored by some Jamaican tourist board or something.”
“And they had a draw or a raffle?”
“No, they had all the girls dance on stage and the winner was whoever got the loudest cheers. It came down to me and Daniella and instead of facing off, we agreed to take each other so we were cowinners.”
“Wow.” I was surprised and nothing more, but I must have sounded put off because Summer took it the wrong way.
“Are you jealous?”
“No, not at all.”
“You’re jealous!”
“I’m not,” I protested.
“Wow. One conversation about marriage and you think you own me now?”
“C’mon, that’s not fair. I’m not jealous and I know I don’t own you. Why would you even say that?”
“Because you’re sulking and you look pissed.”
Summer had been other guys the whole time we were together, so the thought of her thinking that I was suddenly jealous was strange to me. Maybe our conversation affected her more than I realized and she was projecting.
“I’m not sulking or pissed. I’m happy for you.”
She ignored what I said and went on with the narrative in her head.
“Well, you can get over it on the couch tonight.”
Summer got up and made her way to our bedroom. Before reaching the end of the hall, she turned back and looked at me, her face red with anger.
“You know what? I didn’t bring a man home tonight. I was going to let you stick your little dick in me because when I get back from Jamaica my pussy is going to be stretched the fuck out for a month, but there’s no way you’re getting any now.”
The next morning Summer realized that she overreacted, but couldn’t shake the idea that I was against her going for some reason. I was in our kitchen, still in my boxershorts when she woke up and made her way out of our bedroom.
“Look, if you don’t want me to go, I won’t go, ok?”
“I want you to go! I don’t know where all of this is coming from.”
“Are you sure?”
“Yes, I’m sure! I’m happy for you!”
“Come here,” she said as she patted the spot next to her on our couch.
As I sat down beside her, her hand immediately went to my crotch expecting to find my cock but instead grabbed my chastity cage.
“Oh, I forgot. How long has it been?”
“A week.”
“Let’s get you out of there.”
She wore my key on a leather necklace, and I think often forgot that it was even there. I never did. Seeing it dangle from her neck every day tormented me. When she unlocked me, my cock instantly sprung to life. It had been a while. Summer stood up before me. She was only wearing a tshirt and a pair of Frenchcut panties, which she took off before climbing on top of me. Without saying a word, she reached down and guided my cock into her already wet pussy. It had been a long time since we fucked and it was hard not to cum on the spot. She lowered herself onto me, and with my cock buried as deep as it could get into her, she pulled her shirt over her head putting her tits on full display right in front of my face.
She began to speak as she moved her hips ever so slightly.
“You know I’m going to be an absolute slut when I’m in Jamaica, right? I’m going to get fucked as many times as I can.”
I couldn’t even speak, I had to focus all of my energy on not nutting. She started to gyrate a little more, then raised and lowered herself very slowly on my shaft. She leaned into me, putting her mouth next to my left ear.
“Just think about me in a country full of nothing but big black cocks. I bet the guys down there are like vultures when they see white women on their own.” She pulled away to see my reaction, but probably already knew from the way my cock was twitching inside of her. She picked up her pace and was now sliding up and down on me.
“I have one thing I want to do down there, one fantasy I have to experience. I want to get gangbanged. Not just three or four guys, I’ve done that. I want a room full of hung studs to just fuck the shit out of me, one after another. I want to be used and fucked over and over again.”
I couldn’t take anymore and shot my load into Summer. I didn’t even last two minutes. She pulled herself off me and let out a bit of a laugh.
“I think that proves you’re not jealous. You want this to happen, don’t you?”
“Yes, I’ve been saying that all along.” My head was still in a postorgasm cloud.
“Clean up and get your cage back on before I grab a shower.” She kissed me on my forehead before heading back to our bedroom.
This next part is going to sound crazy, and I won’t blame you if you don’t believe it. There were so many different ways we could have handled this but settled on the dumbest possible solution. There have been so many times in my life where I’ve wanted to tell people this because it’s hilariously stupid, but I just couldn’t because of the circumstances surrounding it. So, this is it, I’m telling it here for the first time.
Summer spent the weekend before her trip to Jamaica at her parent’s place, they had an on and off again relationship, but were in a phase where they were trying to be civil to each other. When she came home, she had an anxious look on her face and I knew something was wrong.
“You’re going to kill me,” she said as soon as she walked in the door.
“What’s wrong?”
“I told my parents about Jamaica, well, sort of anyway.”
“What do you mean?”
“I told them that you’re going, that we’re going together. And they’re having a going back to school party for me when I get home.”
“So?”
“So we can’t show up there with me all tanned and you white as a ghost!”
“Just tell them I couldn’t get the time off work and Daniella is taking my place.”
“I can’t! I didn’t want to tell them that we won the trip by dancing on a stage in a Jamaican club, so I told them that you got the trip as a bonus from work!”
“Just tell them I got sick or something.”
“I can’t, your work would just rebook the holiday.”
“So what are you going to do?”
A sheepish look came over her face.
“I spoke to Maddie.”
“And?”
Summer was hesitant, then just blurted out her master plan. “She needs help closing her cottage for the season. You’re going to go there and help her do that while I’m in Jamaica and everyone will think that you’re there with me.”
“What?!” I didn’t think she was serious.
“And you’ll need to go to a tanning salon so that it looks like you’ve been in Jamaica,” she added.
“No. This is the dumbest thing I’ve ever heard in my life. You can’t be serious.”
“You have to!”
I spent the next hour trying to convince Summer to do anything other than what she’d come up with, but I couldn’t get her to budge. In her head, this made perfect sense. but to me, it sounded like a rejected plot from an 80’s sitcom.
“It’s the only thing that works. It gets you out of the city so no one will see you, and it will be a vacation for you too.”
“Summer, this is insane. You want to pretend that we’re in Jamaica together, and I have to leave the city and get a fake tan so that people at your backtoschool party will believe it?”
“It will work!”
“It’s absurd! And I don’t even think I can book a week off on this short notice.”
“I think you should quit your job anyway.”
“Now you want me to quit my job to sell this stupid plan?”
“No, I think you should quit your job regardless. It’s not going anywhere and you know it. Quit your job, go up North with Maddie, and when you come back start looking for a job with a future.”
That was the only part of this plan that made any sense, and ultimately why I agreed to it. Since our marriage talk, I knew some of Summer’s uncertainty with me was that my career prospects looked bleak and I needed to fix that.
“And you’re ok with Maddie and I being alone in a cottage for a week?”
“Maddie’s not going to fuck you,” she said with an incredulous laugh. “And besides, you’ll be in chastity the whole time. I don’t care what you do with your mouth. You’ve gone down on her before. If she wants you to lick her pussy, go for it.”
“This is so stupid Summer, I can’t believe that you actually want to do this, but it seems like I’m not going to be able to convince you of anything else.”
If ‘hairbrained scheme’ ever needed definition, this was it.
I gave work my twoweek notice, and after getting a letter of recommendation from our HR department, I didn’t show up for the last week. That was the week I spent with Maddie at her cottage about an hour North of the city while Summer and Daniella were in Jamaica.
Less than a week later, I loaded up our car with Summer’s vacation suitcase and travel bag, plus what I needed for the cottage, and we picked up Daniella at her place on our way to the airport.
When I met Daniella, she looked exactly how I imagined she’d look. She looked Italian and was. Her Mediterranean ancestry gave her a slightly darker complexion, but she couldn’t be mistaken for anything other than white. She had long, dark brown hair and matching brown eyes. She was shorter than Summer but had a similar shape and body type. It was Fall where we were, and while Summer was wearing a pair of cutoff jean shorts and a tank top anticipating the weather in Jamaica, Daniella was wearing a short dress that barely covered her ass, evidently anticipating something else in Jamaica.
“It’s so cool that you’re ok with this.” Those were the first words she spoke to me, even before saying hello or allowing Summer to introduce us. After a couple of minutes of small talk, she asked me if I could bring her suitcase down from upstairs, which I did and loaded into the car.
It was only a short drive to the airport and Summer and Daniella mostly spoke to each other, but occasionally Daniella would ask me something. At first, I couldn’t tell if she was genuinely curious, mocking me, or factchecking things Summer had told her.
“You really don’t mind that your girlfriend is going to Jamaica without you?”
“I don’t mind at all.”
She shared a look with Summer, who nodded at her before she continued.
“And you know that we’re going there to get fucked?”
“I know. It’s ok.”
“And your cock is locked in a cage?”
Before I could answer, Summer stepped in. “That reminds me, I gave your spare key to Maddie last night. I’m going to keep wearing this around my neck in Jamaica,” she said as she fidgeted with my key. “Don’t be a brat and bug her to let you out. I told her not to. Wait until I get back.”
“Understood,” I said.
I got the sense that Summer had told Daniella all about us, but part of her didn’t fully believe it until she heard me confirm it. She asked a few more questions, but eventually, she was satisfied and went back to ignoring me and talking to Summer.
Parking is a nightmare at the airport, so we had to do parkngo, which only gave Summer and me a few seconds to say our goodbyes. I watched as Summer and Daniella made their way into the airport, just imagining the trouble they were going to get themselves into over the next week. I jumped back in the car and made my way to Maddie’s place, and then off we went to her cottage.
My time up North was mostly uneventful. Maddie bossed me around the whole time, so it was hardly the vacation that Summer suggested it would be. I cut the grass and did a lot of handymantype jobs, while Maddie relaxed and watched me do it. To make our stupid plan work, every second day I was there, I had to drive an hour to a tanning salon and do a session under a hot lamp. What made things even more insane was that I was in a metal chastity cage, and I had no idea if wearing it while under the lamp would burn me or cause other problems. For my first session, I took one of my socks, ran it under a tap, and then wrapped the wet sock around my cage hoping that would offer some kind of protection. As it turned out, I didn’t need it, but driving home with a wet foot was just another part of this stupid plan. By the end of the week, I was somewhat darker but still didn’t look like I had a proper tan.
I had very little communication with Summer while she was gone. You have to remember that all of this happened before smartphones, wifi, and highspeed internet. I think 3G was brand new here, and Jamaica was years behind whatever our best tech was. For the first couple of days, she sent me an email, only about a paragraph long letting me know how things were going but without much detail. Then a few days went by with nothing from her. On her second to last day there, I got an email simply titled “I did it” and could see there was a file attached.
When I opened the email, it just had one word “Gangbang” along with a picture of Summer. She was wearing a bikini in the colours of the Jamaica flag, sitting on the edge of what I assumed was her hotel room bed. There were three shirtless guys wearing shorts lying in the bed behind her, with three more guys dressed the same standing beside the bed. A seventh guy was out of frame, but I could see his arm reaching in from the right and holding Summer at her waist.
It’s impossible to describe the flood of emotions that came over me as I stared at that picture. I knew it was going to happen. When Summer sets her mind to something it’s a done deal, but having a picture to set the scene so clearly for me hit hard. In retrospect, the funniest thing was how mad it made me. Not because she’d been gangbanged, but because I noticed how dark her skin was compared to what the tanning beds had done to me. The final laugh of Summer’s stupid plan was that it didn’t even work because there was no way we looked like we’d been exposed to the same sun.
It was late in the evening, after midnight, when that email came in. After staring at it for I don’t know how long, I went to get a glass of water before heading to bed. Maddie was still up and was sitting in the living room area of her cottage with her laptop on her lap.
“You got the email?” she asked.
“Yeah.” I didn’t even have to ask which one she was talking about. I knew she’d send it to Maddie too.
“Want to talk about it?”
“Not really.”
“Here,” she said and she tossed me a key chain. I wasn’t quite sure why.
“It’s on there. The key to your cage.”
“Summer told me to wait until she got back.”
“And Summer told me to give you a break after she sent the last email.”
“Really?”
“See for yourself,” she said as she turned her laptop towards me. I couldn’t read it from where I was, but as I took a few steps forward, I could see the same email that Summer had sent me with one small difference. The version sent to Maddie had an additional note that read, “If Grey looks upset, let him jerk off.”
“You think I look upset?”
“I can’t tell, but if you aren’t, it could be our little secret.”
“Thanks,” I said as I began to walk back to my room.
“Not in there. Out here. I want to watch, or rather keep an eye on you.”
I went to sit in a chair opposite from her, but she called me over to the couch. “Come sit beside me,” she instructed, and I did. Before sitting down, I undid my pants. Realizing that’s all I intended to do, Maddie gave me further instructions. “All the way off, your shirt too, and the socks.”
Maddie had seen me naked at least a dozen times, but it felt different without Summer around. It felt like I was cheating on her, which was such a strange thing to feel considering she was in Jamaica getting gangbanged.
Disrobed, I sat beside Maddie on the couch. My cock was already straining against the cage, desperate for release. She used her eyes and gave a quick nod, letting me know that it was ok to let it out. I was fully erect before I got it off.
“Stroke it gently. No cumming until I say so.”
I took my cock in my hand and began to stroke. Maddie tilted her computer screen towards me. “I want you to look at this picture and think about nothing else while you play with yourself.” I didn’t need to be told that; the image was already burned into my mind, and it was all I could think about anyway.
“Look at the outline of that guy’s cock in his shorts,” she said, pointing to one of the guys who was standing beside the bed. “I bet he fucked Summer really good. Think he’s got the biggest cock there?”
I couldn’t answer.
“What about this guy?” She pointed to one of the men who was lying on the bed. “I can’t tell if that’s a thick fold in his shorts or if his cock that goes all the way down to just above his knee.”
Involuntarily, my hand started moving faster.
“Which one of these guys do you think fucked her first? I bet it was that one, he looks like her type, don’t you think?”
He did, they all did, but especially the last guy that Maddie pointed to.
“Do you think she fucked them one after another, or did they all pile into bed together and fuck the shit out of her at the same time?”
“Maddie, I’m going to cum.”
“No, you’re not. Not without permission. Don’t you dare.”
“Maddie, please?”
“I said no.”
I had to slow down, otherwise, I was going to cum.
“I’m going to tell you what I think happened. You tell me if you think I’m right. And get back to stroking. You don’t get to stop. Learn how to control your urges.”
Once again, I did what she told me to do.
“This is what I think. I don’t think Daniella took part in this. Don’t get me wrong, she’s a slut too but I can’t see Daniella getting gangbanged. I think all of those guys in that room were there for Summer. Daniella watched and took this picture, but every one of those giant cocks was to fill Summer’s greedy holes.”
Maddie was making it hard for me to not cum, and I was struggling.
“Maddie…I need…I need to…”
“You need to control yourself. That’s all you need to do right now.”
She paused, making sure that I heard her before continuing.
“This is my best guess. They were probably at the beach, or maybe lounging around the pool in their skimpy little bikinis, trolling for cock, just putting it all out there for the locals to see. And those guys know what’s up. They see two white girls on their own, no husbands or boyfriends around. They know why they’re there. They’re not sightseeing; they’re tourists looking for big black cocks.” Maddie overemphasized the three last words. I had to stop stroking. I was going to cum if I didn’t.
“Grey, if you take your hand off your cock one more time, it’s going back in your cage without cumming. Is that clear?”
“Yes,” I said as I moved my hand back and started stroking again.
“So these cute white girls in their little bikinis get a bunch of attention from the locals and a short time later, they lead them back to their hotel room. That’s a slut walk for the ages. Just imagine Summer and Daniella walking back to their hotel room with this train of seven or eight guys following them. Dozens of people had to have seen them, and every single one of them knew exactly what was about to happen.”
There was a nearconstant flow of precum dripping from my cock at this point.
“I bet when they got in that room, Summer popped that bikini top off right away. Those men wanted to see her titties and she was too happy to oblige. I don’t even think she got their names. She just slid down to her knees and a circle of cocks formed around her and she sucked every one of them.”
“Maddie, please, can I cum?” I was desperate now, to the point of it hurting to hold in.
“No.” She didn’t wait before continuing.
“So your slutty little girlfriend was on her knees gagging on all these huge cocks, and once they were all hard they wanted more than her mouth. They wanted her pussy, and her pussy wanted their cocks just as badly.”
I didn’t dare remove my hand from my dick, but I had to stop stroking. I loosened my grip and pretended to stroke, hoping Maddie wouldn’t catch on.
“Then one of those guys scooped her up from the floor and threw her on the bed. Within seconds, another guy ripped her bikini bottom off and she spread her legs nice and wide, eager to take her first cock. This guy right here, the one we think is her type, he got to her first. He got between her legs and forced his big black cock into her tight little cunt and started her rough. Then this guy here, he knelt beside her head and slid his cock back into her mouth. These two guys, they got on either side, and her hands instantly went to each of their cocks.”
“Maddie…” I begged.
“Go on, you can cum now,” she sounded disappointed.
I tightened my grip. Two or three strokes was all it took for me to cum all over myself. You always feel the weirdest the moment after you cum. All the brain fog that builds up when you’re horny suddenly disappears into postnut clarity. It hits you even harder when you’re sitting naked next to a fully clothed friend, covered in your own cum.
“Lick it up, all of it.”
I knew that she wasn’t joking. Before I started, I thought it was something she probably expected. I licked my hand clean, and as I did so she used a finger to gather some up off my stomach and brought it to my mouth.
“Open wide.”
Not long after, I was back in my cage and had two more days to wait before Summer came home.
