Decided to retroactively give this series of stories a title. I don’t think I can edit titles, and I don’t want to spam by re-posting to change the titles, so Part 1 (College Threesome Turns to Cuckolding) and Part 2 (Threesome Leads to Foursome) will remain as they are.
After the events of the first night of Fling, we decided to dial things back the next day. The girls, especially Alice, were still having a little trouble walking after their encounter with Josh, and so the next day was spent mostly hanging out in my room as Alice and I got to know each other better.
The day after, we went back to the Delta house for a party they were throwing, and shortly after we got there, I saw Josh walk up to Alice. The two talked for a bit, but I was too far to hear what they were saying, and Amy was busy talking to another brother’s girlfriend. Josh gave her a hug, and then Alice scampered over to us before whispering something in Amy’s ear as she giggled.
“What’s up?” I inquired.
“Oh nothing important babe,” Amy replied. “Alice was just telling me that Josh was asking if she was okay since he didn’t see her at all yesterday. And if she wanted to go for round 2.”
I tried to feign a casual level of interest, “and? Is she?”
Amy smirked. She knew me too well. “She said he’s too big for her tight, little pussy,” she reached in and gave my already hardening cock a squeeze to emphasize her words. “Who knows, maybe I’ll go back for a round 2!” she teased before grabbing Alice’s hand and pulling her in to introduce her to someone else.
I knew my face was turning red, so I hurried to the bar to get a drink. I went back to the group that Amy and Alice were talking to, and for the next few hours, we played a series of Japanese drinking games that Alice taught us. We all sucked at the games and lost a lot, so it was still light out when the party started to die down. Some people had already passed out on couches in the living room, and others stumbled out the door or upstairs to their rooms.
Alice and Amy hadn’t lost as many games, so they were comparatively not as drunk, but still stumbling and laughing as we all made our way back to my dorm. When we got back, I almost immediately fell onto my bed. Amy laughed and sat down on my chair, and Alice sat down next to me on the bed and stroked my hair. I felt so relaxed that I thought I would fall asleep any minute, until I felt hands fumbling with my belt. I opened my eyes to see Amy, grinning up at me, as she freed my cock from my pants.
Alice, upon seeing my flaccid cock for the first time, squealed in Japanese. “She says it’s cute,” Amy translated.
My face burned a little. I figured it was meant as a compliment, but I wasn’t sure how I felt about having my dick being described as “cute”.
Neither Amy nor Alice seemed to notice, however, and Amy took my cock into her mouth until it got hard. I soon forgot the “compliment” and focused on what was in front of me. Alice got off the bed and moved next to Amy, and the two licked up and down my shaft and kissed around it. I was in heaven.
After a few minutes, Alice got up and straddled me. I was about to tell her that Amy and I didn’t do cowgirl because I would slip out, but she leaned over and kissed me, holding the kiss as she guided my cock into her pussy. Instead of riding up and down like Amy had previously tried, Alice grinded back and forward on my cock. It was amazing. Combined with the intense kissing and hands running all over my body – I couldn’t hold it. With a groan I came deep inside of her, thrusting a few times as my cock throbbed inside of her before dropping my hips. My cum started to spill out of her pussy and onto my cock and the bed below, but I stayed there, eyes closed, content. Alice giggled and gave me a quick kiss before putting her head on my chest.
*ahem ahem* My eyes jumped open as I heard Amy fake cough. I’d actually forgotten she was there for a moment. “Well that was beautiful and all, but I’m really horny, and I don’t think Alice came either.” She looked at Alice, who smiled but shook her head no.
“Oh. Shit. Just uh, give me a moment babe. I just need to catch my breath,” I tried to move Alice off of me and sit back up before losing balance and falling back on the bed.
The girls laughed.
“Don’t worry babe,” Amy gave me a quick kiss on the cheek. “Just watch Alice and me have some fun.”
I was tired, drunk, and on the verge of falling into a post-coital sleep, but I could not miss this. I got off the bed and traded places with Amy, who had been sitting on my chair.
The two girls began kissing, gently at first, then more deeply. They both took their tops off, and Alice gave Amy’s chest a jealous look. “So big! Not fair!” she grabbed Amy’s boobs as she said this, squeezing and fondling them.
“But yours are so cute!” Amy replied as she pulled Alice’s bra off. Alice responded in turn by pulling Amy’s bra off. “Mike, who do you like?” Alice asked me.
“Uhh…well you’re uh…both beautiful..” I stammered.
Amy rolled her eyes. Alice giggled again. Then the two were back at it, making out, playing with each other, and eventually stripping naked. This time, Amy took a look at Alice’s cleanly shaved pussy.
“If anything isn’t fair, it’s how beautiful your pussy is! I wish mine looked like yours,” Amy whined. “No, you are more beautiful!” Alice countered. “Mike??” she turned to look at me.
Why did she keep putting me on the spot like this?? “Uh…they’re both beautiful. I mean, your pussies are both beautiful. I mean, you’re both beautiful,” I fumbled.
Amy rolled her eyes again. “Ugh. Mike. Come on, just answer the question!”
“Or else punish!” Alice chimed in.
“Wait what, punish?” I was not expecting that.
“Yeah, punishment!” Amy gleefully agreed.
I didn’t know what kind of a punishment giggly Alice could give, but I was sure I’d like it, so I played along, “well, I dunno. I can’t decide who’s sexier, so maybe I do need to be punished.”
Alice jumped off the bed and started rummaging through her bag. I was starting to have second thoughts about this when she pulled out a number of colorful dildos. No wait, they were strap-ons. She handed one to Amy, and then put her legs through the straps of another.
“Wait what kind of punishment is this?!” I asked.
“Relax, babe,” Amy assured me. “Alice told me she’s been doing this with some of the guys she hooks up with and said it’s a lot of fun. I thought it would be fun for us to try. Please? If you don’t like it, we’ll stop immediately.”
While Amy would occasionally stick a finger or two into my asshole, especially while sucking my cock, I hadn’t tried anything bigger, and definitely not as phallic as a strap-on. We had talked about pegging before though, and looking at the two beautiful girls in front of me, I figured now was probably the best opportunity I would get. I guess I could give it a shot.
Alice and I moved over on to make room for Amy on the bed, and she sat down behind Alice. Alice turned to face me, and we started making out again. She took my hands and placed them on her small breasts. I soon felt a pair of hands joining mine, and opened my eyes to see Amy reaching around to play with Alice’s erect nipples.
“Turn,” Alice instructed me. It was a bit of a tight fit, but I manged to get on my knees, my hands against the wall that abutted my bed, and I felt Alice shift closer to me. A small wave of anxiety and nerves hit me as I felt her small hands on my waist. Was I really going to take a dick in my ass? I mean, it wasn’t a real dick, but it certainly felt real.
“Ohhhhh,” I involuntarily let out a loud moan as I felt her enter me. Fuck that felt good! Not just the physical sensation of having something in my ass, but the feeling of being pressed up against a wall by Alice. She wasn’t even moving inside me, but I felt like I was being dominated by her. And it make my cock throb violently.
“You like?” Alice leaned over and turned to face me with a smile.
“Yes. Ohhhhh. Yes. I like,” I could barely manage to get out.
“Ah!!” now it was Alice’s time to exclaim as she shifted forward. I bent my neck to look and saw Amy, a look of intense focus on her face, and I could tell that she was fucking Alice with the strap-on. And with each thrust, I felt Alice move back and forth as well, each movement transferring to her strap-on as it moved in and out of my ass.
A mix of moans in English and Japanese filled the room along with the sounds of our bodies slapping against each other as we continued this sex train. I didn’t know how much more of this I could take.
“I’m gonna cum. Fuck I’m gonna cum. Oh fuck Alice I’m gonna cum!” as I started to moan louder and louder, Alice reached around and started stroking my cock. It didn’t take much longer before I was shooting a load all over my pillow.
Throughout my orgasm, Amy continued to fuck Alice, and the reverberations from her thrusting continued to move Alice’s strap-on in and out of me.
“Too sensitive. Please. Need. Break.” I pleaded. Amy stopped and pulled out of Alice, allowing her to pull out of me. I shuddered as I felt the strap-on pop out of my ass, my asshole pulsing as it re-adjusted to not having something stretching it out. There wasn’t enough room on the bed to lie down comfortably, so I pushed my pillow onto the floor, cum-side down, and rolled off the bed.
I looked up to the girls peering over the side of the bed.
“Did you like?” Alice inquired.
“Yes. Thank you,” there was no denying it – I loved being pegged by her.
“Watch,” she demanded, before turning back to kiss Amy again.
I had no problem with that. From my position on the floor, I watched as the two made out, hands roaming each other’s bodies, stopping to grab an ass or pinch a nipple, until Alice pulled away and pushed Amy down. She deftly undid the straps on Amy’s strap-on, throwing it aside before she did the same with hers. Then, from her pile of sex toys, she procured a third strap-on, this one noticeably bigger than the others. While the other two had been relatively small, around the size of my own penis, this one was both longer and thicker. Not absurdly large like Josh’s cock, but definitely above average in both length and girth.
While staring deeply into her eyes, Alice began to penetrate my girlfriend. “Ohhhhhh”, the two girls both moaned as their bodies intertwined. Alice kissed Amy, and I could see Amy furiously kissing her back. I felt my dick getting hard again as my girlfriend and her best friend fucked on my bed. No, fucking sounds too carnal. What they were doing really could only be described as making love. Their bodies were wrapped around each other, undulating as one, their moans revealing a depth to their relationship that I hadn’t known.
Alice said something to Amy in Japanese. Amy repeated it back. I don’t know a word of Japanese, but it was obvious what they’d said to each other: “I love you.”
I was speechless. So incredibly aroused that I thought I might cum again without even touching myself, but also shocked by what I was seeing and hearing. When I’d watched the two girls fucking Josh, while it was obvious that they enjoyed his massive dick and sexual prowess, I didn’t see the same passion and intimacy that I was seeing now. I almost felt a bit embarrassed, as if I were an outsider intruding on a couple expressing their love for one another.
They continued like this for at least half an hour, and I heard Amy cum multiple times. I couldn’t help but jack off at one point, quietly moving to my chair to grab some tissues without disturbing them, the whole time unable to tear my eyes away from the sight in front of me. Amy and I had romantic sex sometimes, but it was one thing to be a part of it and another to watch it.
Amy came one more time, babbling in both Japanese and English as she did. Alice finally pulled out, her strap-on dripping with Amy’s cum, and kissed her lightly on the lips. She carefully got off of her, then stroked her face and hair gently as Amy fell asleep.
She then got off the bed and turned to me with a mischievous look in her eye.
“Suck it,” she ordered.
“I’m sorry?” did she just tell me to suck it?
“Put it in your mouth,” she clarified slightly hesistantly, as if she were questioning whether she’d phrased it correctly. And with that, she stepped forward and thrust her strap-on into my face, reaching a hand behind my head to pull me in. I opened my mouth and took as much of it as I could before I started gagging.
I pulled away and she laughed. “All of it!”
I could see from my fresh saliva marks where I’d gotten to – around three quarters of the way down. I’d never realized that sucking dick, especially a big one, could be so hard. But she thrust her hips forward again, so I opened as wide as I could and slowly worked more and more of her strap-on into my mouth and throat. Finally, I felt my nose touch her stomach.
“Good boy!” she patted my head. If she weren’t so cute, I would’ve found this incredibly degrading. As it was, I was so turned on by this act of dominance. She placed her hands on either side of my head and proceeded to slowly facefuck me. I could feel my dick growing as she thrust in and out, going just deep enough to make me gag a little with each thrust.
“Do you love Amy?” she asked, releasing her grip on my head.
“What-” I stammered as I pulled away from her strap-on, caught off guard by the sudden question.
*thwack* Alice cockslapped me, and a trail of saliva connected her strap-on to my face before she pulled it away.
“Do you love Amy?” she repeated, emphasizing each syllable with a light cockslap, a decidedly more serious note in her voice.
“Yes, I do.”
“Good. Amy loves you. You love Amy. I love Amy.” I wanted to ask if she meant that she loved Amy as a friend or as more, but her tone didn’t invite questions. She proceeded to take her strap-on off, tossing it unceremoniously on top of the pile of sex toys, where it stood erect like a monument to what had just happened in my room, and then curled up on the bed next to Amy with a content smile on her face.
I sat there, dumbfounded. I shook my head, hoping it would clear my thoughts, but my still slightly sore asshole made it hard for me to think about anything other than getting fucked by Alice. And so with my bed occupied, I decided to take a shower.
I probably took a pretty long shower, since I was wrapped up in my thoughts, and when I came back Amy was already awake and on her phone, trapped underneath Alice’s arm, whose owner was sleeping peacefully. Amy looked at me, and then looked at my phone on the desk. I grabbed it and saw that she was texting me.
“hey dont wanna wake Alice up”
We texted back and forth for awhile, occasionally pausing to look up at each other. Amy told me a bit more about how she and Alice had gone to an all-girls boarding school together and shared a room for around 4 years, during which time they had done some experimenting with each other.
“so did you two have sex like just now?”
Amy looked up at me and blushed a deep crimson.
“we were mostly just curious and tried using her brush handle as a dildo lol
nothing as…intense as today”
Intense was definitely one way to put it. I wondered how Amy felt about me relative to how she felt about Alice. And how Alice felt about Amy. I pried a bit.
“were you two ever in a relationship?”
Amy’s face took on a brighter shade of red. She shook her head.
“noo we talked about it, but we both agreed that while we were attracted to both men and women, we wanted to be in relationships with men”
Alice started to stir at this point, and so our conversation ended here as the two of them went to go take a shower together, during which time I fell asleep.
The rest of the week, we continued to party in the day and have sex at night. One night, Alice and I DPed Amy. The next, Amy and I DPed Alice. But as amazing as these nights were, I kept thinking back to getting pegged by Alice, and then watching Alice and Amy make love.
On the night of the big Fling concert, Alice actually asked if she could have sex with Josh again, but just the two of them. We gave her our permission (not that she needed it to be honest, but we were happy to oblige), and Amy and I enjoyed a night alone together – which was nice. I’d forgotten with everything going on that I’d been so busy pledging prior to Spring Fling that Amy and I hadn’t really spent a quiet night together like this in awhile.
Sunday rolled around, and it was time for goodbyes. Everyone swooned when Alice shed a tear while hugging everyone in the Delta house goodbye, adding a kiss on the cheek for Josh. Amy, Alice, and I called a cab from there. The girls held hands silently the entire ride, occasionally making some noise as if to start a thought, only for the silence to return. At the airport, a tearful goodbye finally broke the seal as they made promises to call and text. Alice gave Amy a big hug and promised that she’d be back, sooner rather than later, and then turned and gave me an equally big hug. Then, she patted me on the head.
“Be good boy while I am gone!” she flashed me a mischeivous grin.
I hadn’t expected that. I felt my face flush as I avoided Amy’s curious gaze. Alice turned to wave goodbye one last time before walking through the gates, and then she was gone.
Source: reddit.com/r/gonewildstories/comments/hickyh/adventures_with_amy_part_3_mff