Big U Pride Ch. 04: No Looking Back

Story Info
Brit and the bois become who they are meant to be.
30.2k words
4.75
21.8k
44

Part 4 of the 9 part series

Updated 06/10/2023
Created 05/11/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Getting out of the cab, I walked up steps to the stoop and read the names on the apartment mailboxes. I followed it down until I saw the one I was looking for, "Johnny DeMarco & Lily Fields." I rang the doorbell and waited.

I looked around while I was waiting. Standing there in my trench coat, I felt a bit sneaky, but didn't think I looked out of place. This was just off campus where a lot of the senior class lived. It was nice, to have your very own apartment and be out of the dorms. But I liked living in a house with all my best friends.

The door opened in front of me and a beautiful brunette wearing a shiny silver club dress stood there.

"Oh great! I'm so glad you found the place. Come on up!" she said, gesturing me inside.

I followed her upstairs to the second floor where she guided me inside her apartment. I took off my shoes and dropped my duffel bag by the door. I was now barefoot walking around, still with my trench coat on.

"I'm really grateful the girls were able to send you over on such short notice!" she said to me. "You are really a lifesaver. My bestie Erica is doing a big bash for her 21st birthday and I just HAD to go. It's all weekend up at her parents' lake house so I'm so so happy you had the weekend free to help me!"

She showed me around the place, which was a really nice apartment compared to the dorms that the freshmen lived in.

"I am so happy they chose me to help you today!" I said, enthusiastically. I knew my manners.

"So, long story short. My boyfriend Johnny will be here while I'm gone. He's really great, usually, but I found out that last weekend he got a handjob from some freshman slut during the Zeta party! I mean, I tracked her down and told her to stay away from my man, but how can I be sure he won't do something like that again?"

I nodded as she told me her story.

"And, like, I get it. He's just transferred here from an out-of-state college to be a shortstop on the baseball team and he's going pro next year so all these freshman sluts on campus want to get a piece. And, like, he's practically got a baseball bat for a dick so they all know the rumors."

She had my attention. I could feel my heart rate start to pick up.

"Anyways, I need to make sure he doesn't get into any trouble while I'm gone and fuck some random pussy. After all, there's another Zeta party this weekend and he really wants to go. But I nixed that plan off the bat!"

I nodded, listening to her go on.

"So yeah, that's where you come in." she said as she guided me to the door to their living room and opened it up.

There I saw the infamous Johnny DeMarco lazing on the cough, sitting back and spreading his legs, wearing a white tank top and gym shorts while he drank a beer and watched ESPN.

"Honey, I'm so glad you promised to stay out of trouble this weekend, and I totally trust you not to screw up like you did last weekend. But just in case, I asked the cheer squad to lend me one of their Cheerbois for the weekend."

"I'm telling you, it was barely anything, she just wanted to feel it. That's all."

"Look, we already talked about this and I forgive you. I just need to have a little bit of peace of mind while I'm on my trip this weekend. I can't have fun if I'm nervous about what you may be up to."

"I promise, it won't happen again." he said.

"And I believe you, honey!" she responded. "It's just for one weekend, just so I feel better." She walked over to him and rubbed his shoulder as she talked to him.

I just stood there in my trench coat watching this.

"This here is..." she said to him. "Actually I didn't even get your name, sweetie?"

I looked at her and spoke up. "Brit."

"Ah yes, Britney. Lana's favorite." I blushed as she said that.

"Well, Johnny." she continued as she massaged his shoulders. He barely looked up at me, just drinking his beer and watching ESPN. "Well Johnny, Brit here will keep you company all weekend and make sure you don't get into any trouble. Isn't that right, Brit?"

I responded readily, "Yes, Lily."

"Honey," she said to Johnny. "Won't you even greet our guest?" He hadn't looked at me the whole time.

"I just don't think this is necessary at all. I'll be fine, you can trust me." he said to her.

"Oh I know you can honey, but this is just for me to feel less insecure. And I think you'll like having the company." she said to him.

"And why's that?" he said.

"Well, this isn't just about having a chaperone to watch you. This is something different, one of the new programs that the girls over at the Kappa House have come up with. It's called the Sissy Sitters program and it's designed just for this sort of occasion."

"How so?" Johnny was now a little interested, maybe after hearing this was a Kappa House program, or that it was a sissy thing.

"Well, when girls like us having guys like you who need to be watched for some time so we don't worry about you cheating on us with some skanks -"

"I told you, it's no big deal!" Johnny interrupted.

"I know." Lily kept going. "But when we need to make sure you don't get into any trouble, we need some 24/7 monitoring. And we sure as hell can't have that chaperone be one of your male buddies, cuz we all know that'll just end up with you at the parties. And we definitely can't have it be one of our girlfriends, because you may end up cheating with her."

"So then why not just leave me alone and trust me?" Johnny said sarcastically.

"Oh honey, I wish I could do that. But the Sissy Sitters program solves all my problems." she said.

"Oh yeah, how so?" Johnny asked. This whole time, I just stood at the doorway watching them talk, trying to be polite. I was still wearing my trenchcoat, not wanting to make myself too comfortable in this new home.

"Well, I know that your just too much of a man to not want to get his rocks off every opportunity you get. And I can't keep you from leaving the house and finding your fun. So instead of using the stick, we use the carrot."

She kept going.

"See, honey. I just want to keep you loyal and I can't have you cheating with other girls. But I know you have needs and I can't always be around to help relieve those. Plus, I just don't have the time and energy to help you out every time you get a boner and need to get off. A girl's got to get an education!" she said.

"So what, then? How is this weekend gonna work out?" Johnny asked.

"Well, the Sissy Sitter program keeps you loyal while also making sure your needs are met. You see, Brit here -" she looked at me.

"Actually, I should say Sissy Britney here, will be your Sissy Sitter this weekend. He, I mean she, will make sure you are taken care of."

She got up and stood next to me.

"You see, honey. You may actually end up enjoying this weekend after all, even though I know you'll miss me. Sissy Britney will make sure you stay in the apartment all weekend."

"What the fuck? How am I going to enjoy this weekend if I can't even leave my own apartment?" Johnny said.

"That's because you won't WANT to leave the apartment." Lily said, and then looked at me.

"Sissy Britney, show my man what he gets to play with all weekend."

At that, I untied the knot of my trench coat, opened it and let it fall to the ground.

Johnny was practically tongue-wagging at the sight.

I stood in front of him wearing a white lace apron with ruffles, attached to black elastic garters and adjustable criss-cross back straps with a ribbon waist tie. That didn't hide my matching black lace G-string that tucked away my tiny sissy clitty. The outfit was finished with a neck ribon and a maid cap. I looked like a slutty french maid, and I just stood there letting Johnny drink in the sight.

"Now, Sissy Britney, tell me how you will keep Johnny busy all weekend in this apartment and keep him from getting into trouble with skanks and parties."

I looked at Lily then down at Johnny.

"Well, sir. I have been trained to serve Alpha men like you with lots of different methods. I can tell you all the details later, but for now you should know that for the next 48 hours, you have complete access to this -"

I brought a finger to my lips and opened my mouth, pointing inside.

"And this." I said, turning around for him, pulling aside my g-string and showing my the bejeweled butt plug buried in my ass.

"And you can have these any time you want them, any way you want them. My job is to keep you satisfied and happy all weekend."

"You see?" Lily said to Johnny. "Isn't this better than doing stupid stuff with your friends or some dumb skanks?"

"But," Johnny said, still staring at my sexy body. "I thought you said you didn't want me to cheat on you."

"Oh silly," Lily said. "Fucking a sissy isn't cheating. This is what they're here for, to make sure guys like you are satisfied 24/7 and girls like us aren't busy chasing your every desire. This is just natural. Obviously it's not cheating, you see her only as a sissy to give you pleasure, nothing more. I won't worry about you running away with her like she's a new girlfriend, or worry about rumors around campus that you're with someone else. I can't have that reputation for us. We're making pro next year!"

"Wow" Johnny said, his attention focused on my assets. "Well, if you say so. If this is what happens every time you leave for the weekend, then tell your friends that they should take you away all the time!"

"Don't get too ahead of yourself, mister." Lily said. "Now, Britney, I think you can handle yourself form here." She went over to Johnny, "Behave yourself, ok? I mean, go wild with her, but still behave!" she laughed and kissed him before leaving the room and heading out the door.

But before she left, she called out, "Oh, and Britney - feel free to wear any of my lingerie if you want, just make sure to wash them and have them folded back in my drawer before I get back!"

"Yes, Mistress" I said, reflexively.

It was just me and Johnny now. A silence hung momentarily in the air.

"How can I serve you now, sir?" I asked, staying standing, upright with my hands behind my back.

"Well, ummm...I don't have much experience with you sissies. I mean, when I transferred here the guys on the team tell me that you all are a riot, but I haven't tried it yet."

I wasn't used to a newbie.

"Well, I can do lots of things for you. Starting with cleaning, cooking, tidying up. And, of course, like I said, you have free access to my holes whenever you desire."

"Umm, wow. I guess lunch would be great."

I walked over to the kitchen to get started. I felt weird being barefoot so I went over to my duffel bag and pulled out some kitten heels and put them on. I got busy making this man a sandwich and a side of chips. I was a little lost at first trying to find all the ingredients in the fridge bu eventually I put together a nice sandwich.

I walked over to him, now looking taller in my kitten heels, and leaned over at the waist and put the plate in front of him. He was back to watching ESPN but I knew he had stole glances at me while I was in the kitchen.

"Oh, nice, thank you." he said.

"Of course, sir!" I responded. His manners were a surprise for an Alpha. It was nice, though I wouldn't mind either way.

He was about to pick up the sandwich before he looked at me again.

"So, like, are you hungry too? Want to make yourself something?" he said.

"Oh no, sir! I already had my smoothie for the day!" I said, still standing there.

"Well ok." he said, and started eating the sandwich while watching the game. I kept standing there, waiting.

He stopped eating for a second.

"Do you want to take a seat? You must be uncomfortable just standing there in those shoes."

"If that's what you would like, sir!" I said, and got on my knees in front of him.

"Oh, that's not what I meant but yeah ok." he said, and kept eating his sandwich.

Even though he was watching sports on tv, he couldn't help but look at me in my sexy maid outfit. I noticed that he had started developing a nice tent in his gym shorts. He tried re-adjusting so it wasn't as visible, but it kept growing.

I looked at him as he finished eating and sipped on his beer.

"Sir?" I asked.

"Um, yeah?" he said.

"I notice that you have gotten aroused. Lily gave me strict instructions to make sure you were taken care of. Would you like a handjob or blowjob while you drink your beer and watch sports?"

"Oh...I...Yes." he said.

I perched up on my knees in front of him and grabbed the waistband of his shorts as he lifted his hips to assist me. How kind of him!

I pulled down and got the shorts down to his feet, and looked back up.

Lily wasn't lying, his cock really was like a baseball bat! It was thick and huge, probably 10 inches and almost fully hard! I was also uncut, which was new for me. I stared at it for a few seconds, admiring the big blue veins that coursed up the sides.

"May I, Sir?"

"By all means." he replied.

I tenderly picked up his slab of meat and brought my nose up to it and took a whiff. Mmmmm, I loved that masculine smell. I wish that was a car scent so I could package it and smell it whenever I wanted.

"This is a gorgeous cock, sir." I complimented him.

"Oh, thanks." he said, unused to this kind of treatment.

"May I suck on it please? I would love it if you gave me the privilege." I asked him, practically begging.

"Of course, all yours." he said, not used to answering that kind of question clearly.

"All. Mine." I whispered as I brought my face closer to the covered head.

I peeled back the foreskin and admired the pink helmet tip, then licked it all over and got it shiny. Then I got to work, opening wide and taking this cock into my mouth. Wow, this was a really nice cock. So thick, so hot. I stopped for a second and lifted it up and let it flap on my face. Gawd, I love the weight of these Alpha dicks.

I continued, swallowing his cock and trying to fit more and more in me. Johnny groaned aloud in pleasure. Oh I love that sound.

Spit built up around this cock and it helped me slide my mouth faster on it. Before I could even try and deepthroat it, I heard a loud groan from above. Spurt after spurt of hot cum shot straight down my gullet into my stomach. I held my position until the spurts died down, and slid my lips off his cock. It was glistening.

"Fuck that was amazing." he said.

"Thank you, sir!" I said. I licked up his cock of any remaining cum.

"Oh wow, you don't miss a thing!" he said.

"Of course! Us sissies are trained to serve you completely!" I said, before giving his cock one last lick and pulling his shorts back on.

I sat there for the rest of the afternoon, on my knees, as Johnny watched more sports on tv. He had me fetch him more beers and would sometimes pat me on my head gently.

He then took a nap through the rest of the afternoon while I cleaned up the apartment wearing just the g-string, garters and cap.

Around 9 pm I heard him wake up and walk over to the shower. I joined him inside as he was stepping into the shower.

"What's up?" he asked me.

"I just wanted to see if I could be of assistance, sir!" I responded.

"Oh, how so?" he said, getting in the water.

"By cleaning you, of course!" I said.

"Oh, yeah sure." he said.

So I took off my maid outfit, but kept my g-string on, and got in the shower with him. I grabbed the body wash and generously poured some in my hand and started scrubbing his muscular pecs then down to his abs, before bending over and rubbing the soap over his trunk-like thighs. I admired his Adonis-like body, knowing I never could have looked like this even if I had tried. But that was my old life, and it was way in the rearview mirror.

As I scrubbed up his legs I stopped at his thick cock and balls. Even soft, his cock hung over his sack like a powerful symbol. It emanated strength, a natural strength. I stared at it for a second until I noticed her was looking at me. I poured more body wash on my hand and rubbed it all over his sack and then gently over his cock. I squeezed the head a couple times before letting it go. It started to wake up, but I had moved on before I could give it more treatment.

We finished the shower and I toweled him off. He then went to his bedroom while I put on one of Lily's robes.

About a half-hour later he came out and was all dressed up in a button-down and jeans. He looked ready to go out on the town!

"Oh, Sir, what are you planning?" I asked, wondering why he was all dressed up.

"Just got a text from my boy Sammie on the team. Apparently the Zeta part is getting heated - jello shots off the Sigma Lamba girls!" he said and started walking to the door to get his shoes on.

"But, but - Lily said you weren't supposed to go party this weekend!" I said, desperately as I followed him.

"I know what she said, but she's overreacting. I'm just gonna have some drinks with my boys and maybe do some jello shots off some honeys. Nothing crazy, I can handle myself." he said and started slipping on his shoes.

"But WAIT!" I nearly shouted. He stopped and looked up at me. I even surprised myself, talking this way to an Alpha.

"Just...just wait for 5 minutes in the living room. Have a beer, and let me show you something." I said.

I guess he was so startled by my concern that he took his shoes off and went to kitchen and grabbed a beer before sitting on the couch to drink it.

He looked at me.

"Five minutes." he said, and started sipping.

I grabbed my duffel and scampered over to the bedroom. I needed to be quick. I'm glad I had re-done my makeup after the shower while he was in his room changing. I tore through the contents of the duffel before finding what I was looking for. In record time, I put it all on. I gave myself one look in the mirror before walking back out.

He was nearly finished with his beer as he put it down.

I made a soft mouth-clearing sound to get his attention.

He looked over at me and gave me the same look he gave me this afternoon.

"Holy fuck..." he said.

"Wow," I said. "I'm not used to getting that kind of reaction."

I saw his cock get hard and strain against his pants.

"Now that reaction I'm more used to." I joked, nodding my head at it.

I was standing there wearing high heels, a red bodystocking sheer lace garter dress with opaque detailing. It was complemented by haler ties and matching red stockings. These highlighted crotchless red lacy panties.

"Around the Beta House we call this outfit the 'Man-Stealer', though I know that's the opposite of what Lily wants me to do this weekend!" I said.

He stared me up and down. He saw that I was wearing a read choker with rhinestone lettering. He read it out loud.

"Your Slut." he read.

"That's right, Sir." I explained. "This weekend that's what I am. Your Slut, to do whatever you want with."

I walked over to him sexily, accentuating my strides as my heels made my legs appear long.

I straddled him, my face looking down at him.

"Like I said earlier, you own both my holes this weekend. And I will use them to make sure you follow Lily's orders."

"Wow, this Sissy Sitters program is something." he said.

I reached back and deftly unzipped his jeans without even looking back. Reaching deep inside and struggled for a few seconds before I was able to whip his big cock out.

"We're here to serve Alphas like you. And I'll serve you all night so you forget all about that silly frat party." I started stroking his thick meat as I talked to him.

"After all, you haven't gotten the full Big U. experience if you haven't taken a sissy for a ride." I said, beating his meat.

"Oh yeah? How's that?" he said. His cock felt so hot in my hand.

"The entire baseball team except you has taken me for a ride already. And I'm known around the team as having the MVP." I said, as I teased my boipussy with his thick dick. How I love crotchless panties!

123456...9