My First Cuckolding Experience – High School Prom

I have a confession to make – I am a femdom cuckolding slut. I know it, and I’ve come to accept it. Today I am a devoted submissive to my Mistress. We understand ourselves, and our relationship is strong enough to bring in additional partners. My Mistress enjoys making me a cuckold, and I thrive on the power it gives her over me.

Our individual experiences leading up to our current relationship prepared us for the situation we’re in today. The mutual respect and trust make our Dominant / Submissive relationship work. I look forward to exploring that relationship more in future posts, but it’s important to note that I didn’t always have such healthy sexual relationships. In fact, my first cuckolding experiences were a mix of awkwardness and 

I was submissive to my High School Girlfriend.

I had been dating Trish for my entire senior year of high school. Together we made some discoveries about ourselves. She got off being dominant over males, and I was submissive. I don’t think either of us really understood what that totally meant, but we knew what we liked when it came to sex. I would do whatever she told me. 

I spent a lot of time with her sitting on my face, her favorite position. In fact, she would have me sneak into her bedroom every morning before school. Her bedroom window would be unlocked for me to climb through. It was my job to wake her up, then lay down as she rose and sat on my face for a good 20 minutes. I still remember her morning taste.

We had lots of crazy teenage sex, but always with her in control. As we got closer and closer to the end of our senior year, she started pushing limits more and more. This included displays of her dominance over me in public, mostly in small ways.

I had no idea how drastically it would change at Prom.

My First Cuckolding Experience Happened At My Senior Prom

My high school senior prom was just as cheesy as most. Somehow our student council conjured up the super-original theme: “Under the Sea.”

I dressed in a classic black-tie tuxedo. Trish, of course, had gone with me to the shop and chose the style. She wore a beautiful, sleek light pink number that accentuated her curves. We danced the entire night. Trish was popular, so I was accepted into that crowd by extension of being her boyfriend. At one point, she had me go get drinks, and when I returned, she was dancing with Noah – super hot Noah, the school’s star basketball player. And also Trish’s ex-boyfriend.

It made me uncomfortable, especially watching his hands move down and below her waist. I watched those hands as they slowly squeezed my girlfriend’s ass. Suddenly I looked up and made eye contact with Noah. He was staring right at me as he slow-danced and groped my girlfriend. Then he smirked and winked at me as he slowly turned the both of them. Trish was looking at me, and she, too, had a smirk. What the hell?

Noah was an Adonis

It also didn’t help that Noah was super hot. He was, without a doubt, the hottest guy in the school. At that point, I still hadn’t realized I could enjoy sex with men, but I knew I was attracted to Noah. Who wouldn’t be?

Noah and I had been in the same P.E. class our junior year. It was impossible not to notice his body, in its full naked beauty, as he strutted around the locker room buck naked, his cock swinging.

He looked good, his dick was intimidating and impressive, and he knew it. Plus, Noah had charisma and was the type of guy other guys naturally followed.

Noah enjoyed having others look at him. I know I wasn’t the only guy, straight or not, who couldn’t help looking at him too.

What Happened After My Prom Was Life Changing

After Prom, our friends agreed to meet at the local makeout lookout point. It was a large butte that overlooked the town. There was plenty of room to pull over and enjoy the view. 

I drove Trish’s car, a late model Mercedes her dad gave her, with Trish sitting next to me, discussing the evening so far. I asked her about dancing with Noah, and she smiled at me. Trish told me not to worry about it and then changed the subject. She started talking about someone’s unfortunate green dress, but I couldn’t think about anything other than Noah’s hard body against hers.

When we reached the lookout, she gave me my order to go down on her. I immediately obeyed, reaching across the seat, pulling up her dress, and pulling down her panties. Then, I got to work and made her cum pretty quickly. I had gotten good at one thing by this point – making her cum with my mouth!

When she was done, we both got out of the car to socialize with other couples hanging out. Several people were taking a break from their backseat activities. I joined some guys who were getting high while Trish was surrounded by five or six other girls. 

I lost track of time and Trish. I decided to wander back to her car. I could see the outline of her head through the tinted windows and realized she was waiting for me in the backseat! I was excited as it probably meant she would let me fuck her.

I opened the door, and there she was – getting plowed by Noah. She was on her back, looking me straight in the eye as he was fucking her. I watched his bare ass as it went up and down for what seemed like an eternity, Trish watching me watching him. Then he turned his head and gave me an order. “Buddy, get in and turn on the car and AC.” So I closed the back door, opened the front, got in, and started the car. 

Then I sat there, watching Noah fuck my girlfriend through the rearview mirror.

It was Confusing. Why Was I Okay with Him Fucking My Date?

It was confusing. There I was, watching this guy fuck my girlfriend. It seemed like I should be angry and pull him off her, but it was apparent this was what she wanted. It was also obvious she was enjoying his cock; she kept screaming how good it felt, how big it was, how he needed to fuck her faster and harder.

Trish told me to turn around and watch, and I obeyed. It was cramped, but she spread her legs wide, and I could see his cock as it slid in and out of her pussy. I don’t know how long it took, I think just a couple more minutes of him fucking her as hard as he could, and he came. He came hard and wasn’t using a condom, so I watched his cum smear on his cock as he continued pumping in her for a few more thrusts. 

She and I had been fucking without a condom because she was on the pill. I was confused, unsure how to feel about her allowing another man to defile her the same way.

Then he pulled out, one last shot of cum landing on her. Finally, he pulled up his pants, looked me in the eye, and told me it was my turn. I was a bit frustrated that he was giving me permission to fuck my girlfriend. 

I looked at Trish for direction. She grinned and said, “You heard him; get back here and fuck me.” I obeyed and climbed out of the car as Noah did the same. We stood there, face to face, for just a moment. Then he patted me on the back and told me to get to work.

A Night of Firsts

It turned out to be a night of many firsts. Things that I would do again, many times over. 

It was the first time I’d watched my girlfriend fuck another guy. 

And it was the first time I’d fuck my girlfriend while someone else watched. As I climbed into the backseat of the Mercedes, I pulled off my pants. Noah left the door open and watched as I entered my girlfriend. He commented, asking me if I was enjoying his “sloppy seconds.” 

But I was concentrating on doing a good job; I knew I was expected to make her cum before I would be allowed to do the same. I could see Noah’s jizz smear as my body slid into Trish’s.

“Make sure to make her cum before you nutt,” Noah ordered me. Again, I felt frustrated and humiliated that he was giving me orders. After all, I’ve been able to please my girlfriend, on my own, without Noah’s instructions.

Unfortunately, it also turned me on, and I came fast. Then I experienced another first.

A Whole New Taste

I came inside her and instantly knew I was in trouble. She hadn’t climaxed with me yet, and it wasn’t acceptable that I came before her.

“Did you cum, you little bitch?” Trish pulled my hair, pulling back my head. I was ashamed of my mistake and humiliated at how she treated me in front of Noah.

Noah laughed and told her not to go too hard on me. Then, Trish gave me a new order: “Now, clean me with your tongue.” I didn’t know what to think, and I hesitated. I’d eaten my cum out of her, but now this would be a mixture of both of us.

Noah reached in and smacked my ass hard. “Better do what she says, man!” 

And so, I did. I went down on my girlfriend, experiencing the taste of another man for the first time. The mixture of his and my cum, combined with Trish’s juices, was overwhelming. I remember thinking, “I’d better not pass out.”

After I’d fully consumed all the bodily fluids I thought I could handle, Trish came, and she came hard. She’d never squirted before, but this time there was so much I choked on her. She didn’t care as she screamed out her lust. The car door was still open with Noah watching; I’m sure other people must have heard.

After I finished licking up all her juice, she ordered me to climb off her and get out of the car. So I did and found myself face to face with Noah, still grinning. He winked at me and said he’d see me soon, then returned to his car and, I presume, his date.

Summer of Awkward Teenage Cuckolding Sex

Things really changed with Trish and me after Prom. Trish was no longer satisfied with just me. Sure, I was still expected to show up every morning for her facesitting, but otherwise, we spent little time together alone.

I had a summer job stocking shelves at the grocery store to pay for college. Trish and Noah started spending time together when I was at work. The two would pick me up when I got off, and the three of us would hang out. I ended up feeling like a third wheel with my own girlfriend.

But, the sex was fun, and I just put up with the humiliation because it was also turning me on. All those teenage hormones, my brain was buzzing, and I didn’t know what was happening. 

At first, the sex was just variations of Prom, over and over again. First, I’d watch as Noah fucked her and came inside her. Then, I’d go in for my “sloppy seconds” and make sure that Trish came before I did. 

Then, no matter if I was a “good boy” for making her cum first, it was always my job to lick her clean. I ate so much cum that summer.

Our Last Session

On our last day of summer, we agreed to spend the day together at the lake. Noah was leaving the next day for school and Trish the following day. I still had about a week before I would head to my university.

Once we got to the lake, we all stripped and jumped in the water. We didn’t really care if anyone saw us, but it was a large and isolated location. Most of the summer vacationers were gone, and the place was pretty deserted.

After some time, we climbed out, and all lay on the blanket Trish had laid out. I assumed the two of them were about to start fucking, but she had something else in mind first.

“Baby, I want you to get Noah hard for me. Use your mouth. Get him nice and wet too.” I was stunned. It had been so long since she had given me an order that it made me hesitate. 

“C’mon, dude, do what she told you,” ordered Noah. In a trance, I moved my face to his cock, and without thinking, just opened my mouth. Trish helped by shoving the back of my head down on him, impaling the back of my throat.

Trish continued giving me instructions as we all started fucking, together. By the time we were done, Noah’s cock had been in every hole Trish and I had to offer. 

It was a fantastic way to say goodbye to that relationship. It was the last time I fucked either of them, and I’ll always have a soft spot in my heart for my firsts!