I was ready at 7 am for Jill to pick me up for the first day of school. I wore khaki shorts and was very aware of my smooth legs. I made a sandwich and put it in my bag when I heard the car pull up.
I walk outside expecting her to be in the Mercedes she usually drives, but instead she's sitting in the front seat of the red Ferrari with the top down. She looks beautiful as ever in a flowy black skirt and a tight white crop top that shows off her stomach and tits. I step to the side of the car, "Wow, you're stunning. I can't believe you're mine."
She smiled and patted the seat next to her. I hopped in and tossed my bag at my feet. I turned to her, "So why'd you pick me up so early?"
She smiled and pulled up her skirt to show she had her ten inch monster of a cock hanging out of her panties, "Oh I thought I'd give you enough time for breakfast." Her devious smile made me delirious as ever.
I bent over and grabbed it to kiss it and start teasing her, but she started the engine and said, "I'd hurry if you don't wanna be seen sucking the new girls dick before school, I heard this car is fast."
She steps on the pedal and starts speeding through the trailer park I live in. I panic and realize she's serious, so I start using both hands to twist and stroke while I bob up and down furiously on her cock. I can hear the speed of the car as the wind picks up around us. She flies through the roads and roundabouts. Finally, she comes to a halting stop. She puts her fingers in my hair and pulls me head off, she points at the car next to us and says, "Smile!" Just as I meet the face of an old lady looking back at me, she shoves my head down all ten inches until my nose pressed against her skin, then she starts driving again. I can tell by the turns in the road that I only have a few more minutes before we get to a spot where there might be other students sharing the road with us, and it's hard to not check out the hot blonde in the Ferrari speeding through the roads. I'm doing the best I can when she shoves my head back down hard and I feel her shoot her massive load straight into my stomach. Once she's done, she let's go and I clean her cock.
She smiles and looks at me, "How was breakfast?"
I laugh, "You're crazy."
"Oh you don't know half of it."
We pull into the school parking lot and head to the back like I tell her. Soon several of the soccer guys and my friends show up and we're all hanging out by the cars. Most of them I haven't seen since I started dating Jill, except for the few that were at the party. I'm introducing them all to Jill when a blue Jeep pulls up. I grab Jill's attention, "Oh those are my friends Fiona and Demi, they're just recently a couple, so they're still very into PDA."
Jill squeezes my ass, "I can think of some PDA you did this morning."
Fiona comes running up and gives me a hug, she's a short little redhead, but pretty cute. I would've dated her years ago if she wasn't gay. Then Demi walks up, sexy as ever but also gay. I expect her to say my name, but she says "Jill?" They give each other a hug and I'm confused as ever.
Jill turns to me, "I went to a summer camp with Demi this summer, I can't believe you two are friends!"
The four of us talked for a while even after everyone walked inside. The last warning bell dings and we decide to finally go in. Demi hugs me, "I can't believe you two are dating, I'm so happy for you! And you mister," she pokes my chest, "you better tell me every single detail tonight over shakes."
I agree and walk in holding hands with Jill. Before we reach the door, I ask her how she knows Demi. She squeezes my hand, "We met at a camp for young trans people."
I stare at her in disbelief, "So she knows? Like about you?"
Jill laughs, "Hell, she was there first." My worst fear had just come to fruition.
The whole morning, I was worried that Demi was going to tell someone. I texted her several times telling her that it was a secret, but she didn't respond. Finally, lunch came around and I ran into her. She poked my chest, "You've got a lot of explaining to do mister, I spent all last year trying to get with you and then you go for another trans girl?"
I pull her to the side, "You've gotta be quiet about Jill. She doesn't want anyone to know. And I'm sorry, I didn't know you were into me, or even that you were trans until this morning."
She stared at me incredulously, "You mean you didn't know I had a dick for the last 3 years?"
I shook my head, my face showing genuine cluelessness. She laughed, "Wow, I'm amazed at the male gender sometimes. I'll be quiet, but shakes tonight, you, Fiona, Jill and I. And you're going to spill every detail." She walked away to get lunch. Jill and I had different lunch schedules, so she was in the lunch after me. I hung out with the guys and then headed to English class.
The last class of the day was contemporary literature with Jill. The class was a joke, seniors only took it because it was an easy A and you could spend the whole time pretending to read books anywhere in the school. The first day was just and intro day and so we didn't get to go exploring the school.
After contemporary literature, school ended and we had 10 minutes before we had to be dressed and on the field for soccer practice. Practice went well and we ended discussing strategy for the game on Thursday against our cross town rivals. It was our home opener and our first chance to show the district that we were gonna be a powerhouse. After practice, we showered and then Jill drove us to a local diner for shakes with Fiona and Demi, the thing I'd been dreading all day.
We walked in and immediately saw them in the corner booth, thankfully away from any other customers. They got up and hugged us each before we sat down. Demi started speaking, "So... how did you guys meet?"
Jill took the lead, "It was at soccer tryouts, I saw his cute little ass and knew I had to make it mine."
Demi laughed at that, "I didn't know Nico was into that, I tried all last year to fuck him, but apparently he had no clue."
Jill laughed, "Oh you should've been more direct. He loves it. Yesterday, he woke me up at 5 in the morning riding me cowgirl style because he couldn't wait for me to wake up and fuck him."
The girls gasped, "Oh my God, you lucky girl! I didn't realize he was such a slut." My face turned bright red.
Demi kept going, "Can he deepthroat it all?"
Jill was very excited and into the conversation, "On our second lunch date, he wouldn't stop trying until he could touch his nose to my skin!" The girls all laughed.
Demi turned to Fiona, "Oh you have no idea, she's got the largest dick I've ever seen!" She turned back to me, "Nico, you have to show me this sometime, I can't believe you've been hiding out on me!"
I stammered out a few nonsensical words before I got cut off by Jill, "Oh you have to come by and join us sometime!"
Demi's eyes lit up, "Oh my gosh, I'd love to! I must see this."
The girls all decided that we'd have to find a time for us all to have some fun together. Something I was really not looking forward to. When we got back in the car, we headed back towards her apartment. Her hand holding mine as we sped through the night, wind in our hair, I was very confused about how I felt about this girl. First she would humiliate me all night, then she would make butterflies fly through my stomach.
We went up the elevator to her apartment, and heard the typical sounds of Kiera fucking Jerry as we walked to Jill's room. She closed the door and pulled me close, her lips hovering an inch from mine, "Remember, you're mine now." Then she kissed me and pushed me on the bed. She stripped naked and started pulling my shirt off, "Get me wet." She held her cock in my face and I eagerly went to work, I spit up and down it and slathered my tongue across it. After a minute, she pulls out and flips me over onto my hands and knees, and pulls down my shorts and boxers. She gropes my now shaved ass, spreading the cheeks and squeezing them. She buries her face in between them, licking my hole and sticking her tongue in and out, playing around and exploring my hole. She takes her tongue out while I'm still moaning, "I love your smooth ass even more when there's no hair."
She wasted no time and in one second I went from being empty to swallowing all ten inches of her rod with my ass. I yelped and jumped forward, but she pulled me back at the waist forcing her dick back into me even harder. She continued to fuck me ruthlessly for several minutes. Every time I got close to cumming, she would slow down and gently go in and out or gyrate her hips. Then she would start pounding my ass again until she did the same thing a few minutes later. I was loving every second of it.
She pulled all the way out to the tip and slapped my ass a few times, "What do you want?"
"Please fuck me," I groaned
"Sorry what do you want me to do?"
"Please fuck me in the ass!" I said louder.
"I can't hear you, where do you want me to cum?" Her teasing voice turned me on even more.
"Please fuck me in the ass! I need your hot cum to fill me up!" She laughed and thrusted back into my ass. This time she didn't stop. She kept pressing against my prostate and making me moan like a whore. A couple minutes went by and I screamed, "I'm gonna cum!" My cock erupted with pleasure, shooting stream after stream all over her bed. I finished my orgasm and felt Jill stiffen up and flood me with torrents of her own sticky remedy. Her body collapsed on top of mine and I fell asleep.
I woke up feeling Jill's mountainous breasts pressed against my back and her massive dick still inside of me. Her arms were around my head and she was awake, going through her phone. When she noticed I woke, she took a selfie of us together. She kissed my neck, "That's a cute picture, but you should see the one Kiera took of us, it's adorable."
She swipes out of Snapchat and opens photos to the last one. It's a snap from Kiera of Jill and I sleeping with her on top and inside of me, the caption says, "Can't even sleep without her cock inside of him <3" I cringe knowing there's no way to ever convince Kiera to get rid of that photo.
She thrusts lightly inside of me a few times, then pulls out and lays down next to me. I start sucking on her breasts to her moans. She pushes me away, "I have homework to do so we can't right now." She gets out of bed and grabs her computer to do homework for the rest of the night.
The next few days of school went by fairly normally. Jill would pick me up in the morning, we would either fuck or I'd suck her off, we'd go to classes, and if we could sneak out of final period I would suck her off, then we'd go to practice and head to Jill's afterwards to fuck and then do homework. I was really beginning to enjoy every part of it. I didn't even mind the blowjobs because the submissive role was so erotic and I loved watching Jill go into ecstasy when she came in my mouth. Demi and Fiona would make jokes to me in passing, but they weren't going to tell anyone what they knew about our situation.
Thursday came, the day of our home opener versus our cross town rivals. Jill knocked on my door at 6:45 while I was still getting dressed. I told her to come in and she did. We had to dress formally for every game so that everyone at school knew there was a game. It was a sense of professionalism that didn't make sense for a bunch of high schoolers. I was straightening my tie when I saw her in the mirror. She's wearing knee high black 3 inch heels, black stockings, a tight black dress that ends high up her thighs and pushes her already large tits up and out, and a light pink coat to go over it. I had a hard-on immediately. I turn around, "Wow, you're hot."
She smiles and grabs the end of my tie playfully, "Hot enough to give me a blowjob in the school parking lot?"
I stare at her with fear in my eyes, "What if someone sees us?"
She pulls me close, "It's pretty early in the morning, you'll just have to make quick work of it, I guess. Come on, let's go."
I grab my backpack and start following her out, "Wait! I need to make lunch first."
She grabs my tie again and pulls me along, "Guess I'll be feeding you breakfast and lunch today." The twinkle in her eyes when she has that guileful smile always turns me on. Thankfully, she has the Mercedes today so it'll be tinted windows. I toss my backpack in the back and jump in the front. As soon as I get in, I reach over to start sucking her off, but she hits away my hands, "Wow, I know you're eager to have my cock in your mouth, but you have to wait until we get to the school." Her giggles brought a shade of red to my face.
We pull into the school parking lot and it's almost entirely empty. She parks in the back and there's already another car there. A blue Jeep, but it seems to be empty. We park and she immediately gets out of the car and walks to the trunk. She gets in and puts down the middle row, looks at me and puts out a hand, "You coming?"
She pulls me into the back onto the now flatbed of the truck. It has a thin layer of foam of some sort making it feel like a mattress. She catches me noticing it, "I had this put in so we could have a lot of fun back here." She lays down and pulls out her already hard dick, "Let's 69." She unbuckles my pants and we begin sucking each other off. Thirty seconds after we start, the trunk door opens and I jump up to see who it is.
Demi is standing there and hops in before closing the trunk again. She laughs, "What's got you so scared, Nico?"
I stammer, "What're you doing here, Demi?"
Jill speaks up, "Oh, she wanted to watch you suck my dick so I invited her to watch, but now I'm thinking it'd be super hot if she joined in, maybe fucked your ass? How would you feel about being a part of Nico's first double penetration?"
I tried to protest, but Demi was already stroking her small four inch dick, "Keep sucking Nico, I wanna see you deepthroating while I fill your ass up with cum."
She plunged her dick into me quickly, but I hardly felt it compared to Jill's dick. I moaned a little as I sucked on Jill's behemoth, but it was nothing compared to Jill. I found it hard to focus on the dick in my mouth and the one in my ass at the same time. I felt like a piece of meat, just to be used by other people. It was only a few minutes before Demi hilted inside of me and shot her cum inside of me, a much smaller load than Jill can produce, but then again I've never seen anyone who can cum as much as Jill, even in porn. Demi pulled out and then I felt a cold object get shoved up my ass. Demi laughed, "This is so you don't spill my cum on your nice clothes all day."
Jill stopped sucking and told me to get off. I did and she told me to get on all fours, as I did, she pulled out the plug, which was bigger than Demi's dick, and laughed, "I think I'll let you hold my cum in there all day too! What a great idea Demi, now he'll never forget about me."
She pushed the beginning of her cock into my ass and I already moaned more than I did with Demi. She pushed all the way in quickly and began fucking me. In a couple minutes, I yelled, "I'm gonna cum!"
Jill responded, "Demi, don't let Nico waste any of his own cum!"
Demi dropped underneath me and put my dick in her mouth just in time for me to fill her mouth with my load. Then she got up and started kissing me, depositing it all back into my mouth. I hated when Jill did that, but I was still in my post orgasm bliss so I didn't care. Within seconds of that, Jill started shooting her hot load in my ass too. She kept filling me up and pulling out slowly as she did. When she pulled out all the way, she shoved the plug back in, keeping the cum from flowing out.
She snapped and said, "Clean my off."
I immediately turned around and started cleaning her dick off with my mouth, as Demi said, "Wow, I've never seen anything like that! That's the most cum I've ever seen, and then he just cleans you off afterwards too, that's so hot. I need myself a boyfriend like that."
Jill pulled up my pants and buckled them, then ordered me, "Clean up Demi too, and thank her for fucking you and feeding you your cum for breakfast."
I crawled over to Demi and quickly cleaned her cock with my mouth, then said, "Thank you for fucking me and feeding me my cum for breakfast."
Demi laughed, "This is amazing!"
Jill was proud, "Thank you, he's the best boyfriend anyone could ask for, I'll bet he'd even blow me during school if I asked him to."
I ignored her teasing and we got out of the trunk of the car to head into school. Walking with the plug in was uncomfortable, but not horrible. At least until second hour started, then I got a text in a group chat with Demi, Jill, and Fiona. It was Jill, "Hey Demi, would you mind turning the plug up a setting each period until Nico begs me to fuck him in the bathroom? Thank you!"
I read the message a few times and then on my third reading of it, the plug came to life. It was just a soft buzz in my ass, but I was hard in seconds. My boner didn't go away for the next three hours. By the time lunch came around, I was doing everything I could to not moan loudly at the lunch table. The guys kept asking me if I was okay.
I ran to the unisex bathroom and texted Jill, "Please come fuck me, I can't take this any longer."
"Tell the groupchat why you want me to fuck you, and if Demi turns off the vibrator, then I'll come fuck you."
I sighed in defeat, and texted the groupchat, "Jill, please come fuck me, I need your big cock in my ass right now, I can't wait any longer."
A few minutes went by, and then there was a knock at the door. I opened it and Jill walked in, looking just as sexy as she did this morning. She smiled, "I heard someone needed a dick appointment?"
I looked up at her, "Yes, that would be me."
Her excitement was overflowing, "Ok, get me ready to pummel your ass then."
I got on my knees and pulled up her dress. She unclenched and let her massive dick swing loose, hitting me in the face to her amusement. I grabbed it and began working it with my mouth until it was wet and hard. Then I got up and pulled down my pants, bending over the sink and presenting my ass to her. She walked over and pulled out the still vibrating plug, I could feel cum leaking out and then her wiping it up with the plug. She reached around and put it in my mouth, "Here, I know you always like to be sucking on something too."
I tasted the cum and the juices from my ass, and my mouth vibrated with the plug. Then she shoved her dick into my ass in one push, suddenly I was glad I had the plug in my mouth or people would've heard my screams. She started fucking me as fast as possible so she could get back to class. After two minutes, I shot my load against the tile floor of the bathroom. She lasted another couple minutes, then she pulled out, "Get on your knees and stick out your tongue."
I turned around and got on my knees, she pulled out the plug and tossed it in her bag. She stroked her cock a few times and then shot load after load onto my face and into my mouth. She finally stopped shooting her load, "Remember not to waste any!"
So, I started wiping her cum off and putting it in my mouth to swallow. My eyes were stuck shut so she grabbed some paper towels and cleaned them off. Amazingly, none of her cum got on my clothes. She pulled me up into a hearty kiss. She broke away, "You're the best boyfriend I could ever have, can't wait for my post-game blowjob when I get more points than you," she teased.
I smiled back at her, "Not if I win."
She laughed, "I'd love to see that happen."
I headed back to lunch, but the bell rang first, so I went to my next class. When I sat down, I saw there were several texts in the groupchat, so I opened it. The first was a picture from JIll of me on my knees on the bathroom floor, tongue out, face entirely covered in cum, and a pool of cum filling my mouth. She captioned it, "I'm so glad it's lunch now, I've been starving ever since I fed Nico lunch earlier."
Both girls loved the message and responded, "That's so hot, Fiona you free next hour?" and "Oh my gosh, he's such a cumslut." I closed my phone, not needing the humiliation.
In the last hour of the day, Jill and I sat next to each other on the bean bag, reading our books. I spent half of the time just watching her eyes as she read. She was the most beautiful girl I've ever seen. She turns to me after a while and whispers, "Don't you have a book to read?" I simply lift up the book while gazing into her eyes. She gets a stupid smile on her face, "You can spend all night admiring me, read your book." The day was peaceful up until the beginning of the game.
We stood as a team in the locker room, watching coach James draw diagrams on the board explaining plays and tactics for us. He droned on boringly, "Dewitt is historically worse than us, and I expect the same this year. They will not be nearly as talented, organized, or prepared as you guys are. I would expect them to fill that gap with brute force..."
Jill squeezed my ass and whispered in my ear, "I expect to fill your gap with brute force later." She laughed at her own joke and I just hope no one heard it. Coach kept going on about tactics, but I doubt any of the other players were listening if I wasn't. He wrote the lineup on the board and we headed back out to the field to line up.
The other team laughed when they saw Jill and Kiera starting on the field. They weren't ready for what was going to hit them. The whistle blew and we pressed a high line to quickly intercept the ball. I cut off a forward pass and slipped the ball into Jill. Two guys went flying in to tackle her, but they went with too much force and for her instead of the ball and she easily danced around them. She passed it back to me and made a run forward, I flicked the ball over the heads of the final defender and she volleyed it first time into the net. The crowd went crazy. Our student section was only about thirty kids and then the freshman and JV teams, but I had a feeling it was going to start filling up soon. We thrashed them 7-0 in the biggest blowout against them ever. We knew we would win, but we never thought it would be a seven point sweep.
I scored two goals and had two assists, but Jill still netted four and had an assist. She kissed me as we walked back to the locker room, "That mouth is mine tonight."
Her excitement was contagious. The team was ecstatic with our big home win to start the season. The coach calmed us down, "Good job everyone, it was a very solid overall team effort with some star performances." Everyone cheered Jill's name and clapped. "But remember, we still have seventeen more games until the tournament. We have to focus on our goal and train hard. Practice tomorrow and then we have a game Saturday evening, invite all of your friends, it's a big game against Central!" We all cheered and then headed to the showers, Jill and Kiera left for their own locker room.
I waited by the exit for Jill while she showered. I spent the time talking to teammates, their families, and friends. Everyone complimented or congratulated me on the game. I felt like a champion, like life couldn't get better. Then Jill appeared, dressed as sexy as she did for school. We held hands and walked to her car, she towered over me in her heels. We got to the car and a blue Jeep pulled up, Demi and Fiona were in it. Demi smiled, "Hey guys, amazing game!" We thanked her politely and she went on, "Fiona and I are going to the theaters if you want to join? We brought extra blankets!"
We decided to join them and we followed them to the local movie theater. It used to be a really terrible, rundown place, but a big name theater company recently bought it and turned it around. It now had reclining seats, a restaurant, and even a bar, unfortunately only Jill had a fake ID. We bought tickets to a cheesy romcom and grabbed popcorn. We headed to the theater and found our seats in the back row. I sat in the middle of Demi and Jill, Fiona on the other side of Demi. We each put a blanket over us as the previews started. My hand reached across to grab Jill's hand, she smiled when I grabbed it. A couple minutes later, Demi tapped on my shoulder. I leaned over to her and she whispered in my ear, "You should go down on Jill."
I looked at her and realized she was serious, "In here?"
She nodded her head, "There's no one here, just go under the blanket."
I got out of my seat and crawled to the base of Jill's seat. She knew what was happening and lifted up the blanket for me to go under. She put her seat back to normal and moved forward to give me a better angle. I pulled her dress up and her panties down. Her massive cock flopped out. I kissed the tip and began my teasing ritual when she said, "Go slow, don't make me finish until I tell you."
I bobbed up and down her shaft slowly, played with her balls, and teased her. I went slow and worshipped her cock for almost an hour before she finally said, "Finish me off." Then I picked up the pace and started swallowing her entire cock into my throat, massaging it with my contracting throat. After a few minutes of renewed vigor, her cock stiffened and expanded in my throat before shooting load after load into my throat. I kept milking her cock until she couldn't shoot any more cum down my throat, then I cleaned her off. I put her clothes back and came out from under the blanket, noticing how sore my jaw was.
I sat in my seat and she kissed me passionately, "Now that was a blowjob." Pure elation was cast over her face. I sat back to watch the movie and Demi gave me a huge smile.
------X------
After the game against Central had almost 100 students in attendance to once more watch Jill steal the show, the soccer team became the talk of the school. Every guy in school was jealous of me because I was dating Jill. She was one of the hottest girls in school and she showed up every team we went against. We were the star couple in school, and life couldn't get better. We were undefeated and the state tournament was approaching soon. Coach James called the team over before practice started.
We all huddled around him as he spoke, "Boys and girls, I have great news. We've been invited to the Midwest invitational. The school will pay for the bus, food, and hotels in Indiana. It's next weekend, so we'll have to reschedule the game against Northern, but this is a huge opportunity for college scouts to see you so it's worth it. We will leave school early on Thursday to head down to Indiana." He set us off to warm up after that.
Jill grabbed my hand, "You know what that means, right?" I shook my head no, "That means we get a tournament one weekend and halloween the next, two fun weekends in a row!" I grinned.
The week went by fairly quickly, I spent time at school, practice, and with Jill. Thursday at lunch, we were dismissed for the tournament. Jill and I sat next to each other on the back of the bus with Kiera and Jerry across from us. Jill slept on my shoulder for the long ride. When we arrived at the hotel, coach James gave us the rules on the bus. "Alright kids, no drinking or doing drugs, curfew is at 11, and stay out of trouble." He handed out room assignments and Kiera and Jill were together while Jerry and I were together. We all knew those would not stand. "Meet in the lobby at 9 am for breakfast and to head to the fields."
We headed up to the rooms and immediately changed up the assignments so that Jill and I were together and Kiera and Jerry were together. We got to our room and I closed the door. Immediately, Jill started making out with me. "I need your ass right now."
I stopped her, "We're supposed to meet the team down at the pool in 5 minutes."
"Ok, I guess I'll just be hard in my bikini. Don't worry, I doubt anyone will notice." She knew how to win an argument.
"Ok ok, we'll have a quickie, but finish in my mouth so I'm not leaking while we head down to the pool."
She smiled, "Ok if you want quick, quick it is."
She grabbed me and forcefully carried me to the bed. She dropped me on it and pulled down my shorts and dropped hers. She spit on her hand and quickly lathered up her python. Then she pushed in all the way in one thrust. I screamed in pain and she started fucking me with no abandon. It was brutal and mostly dry. I cried as she fucked me. I came within minutes and soaked the bed in my cum, then she came in my ass, pulling out so it was barely in as my hole closed up again. She walked to her bag and said, "Don't argue with me when I want to fuck, and don't tell me what to do."
I cried a bit more from the pain of the rough and mostly dry fucking and then I stood up. I grabbed my swim shorts and put them on. I clenched my hole as tight as possible and I could feel the cum waiting to pour out. Jill came out of the bathroom in a blue bikini. Her tits held up perfectly, and her bikini bottoms magically hiding her cock. She spun around and showed off the thong back. She looked so hot with her perfect ass on display. She came up and kissed me, "I'm sorry if I was rough."
We headed down to the elevator and I felt the cum beginning to make a wet spot in my swimsuit. We got in and Kiera and Jerry held the doors open. Kiera asked us, "What are you guys doing for Halloween?"
I shrugged my shoulders, "I don't know, I usually do a last minute costume and go to Adam's for a party. Why?"
She grinned evilly and I got scared, "I was thinking we should make it more interesting. Like whoever scores more points picks the other costumes? Jill and I can be a team against you two."
I sized her up, Jerry and I would probably lose against Jill alone unless we both scored a ton. Add Kiera as a wildcard and it was just plain risky. Jill agreed enthusiastically, "Oh I think that could be so fun, don't you Nico? I mean you and Jerry are both attackers and Kiera is a defender. Odds are in your favor, imagine me in any skimpy fantasy you want and tell me you don't wanna see me in it?" Her eyes were tantalizing as she teased me with the fantasy of winning.
Jerry and I looked at each other, knowing we didn't have a choice, and we had a very small chance of winning, "Ok deal."
Jill and Kiera got all giddy, "Oh we gotta start planning their outfits! One for Adam's party and the other for Demi's party!" They laughed as the elevator went down to the pool level. We walked to the pool area, I was getting desperate to jump in the pool and clean out my ass where no one would notice.
The pool area was crowded when we walked in. Jill took my hand and led me over to the hot tub where our teammates were. We spent the next hour joking around and talking about the tournament. Then Jill brought up the bet, "If Nico and Jerry can get more points than Kiera and I this weekend, then they can choose our halloween costumes, but if we get more we pick theirs. I have so many ideas, I can't pick from them!"
The guys all laughed, Nick jumped in, "They have no chance!" and Adam added, "Make it really embarrassing"
This garnered a lot of support, "Don't worry, I'm working on some ideas he'll just love!" She kissed me while we all joked around.
Later on in the hotel room, we were making out while the tv was on. I had one hand on her ass and one slowly stroking her hard dick. She had the same on me. He tongue infiltrated my mouth and explored as if she hadn't been there before. She sat up and moved to the edge of the bed, "Ride me."
I sat up and lined up my hole with her throbbing cock and began to lower myself down on it. I can feel the tip pressing against my hole, then it pops in, much easier than it used to. I moan and slide down on it, almost getting all the way in the first go. I wrap my legs around her waist and lower myself all the way until I'm fully sitting on her. We start kissing as I slowly bounce up and down on her member. It feels incredible with the passion and the feelings up in the air.
I'm slowly riding her as she stands up, carrying me while we're fucking. I don't look where we're going, my face is buried in her tits. I hear a door open and shoot my head up in a panic. I feel the cold air against my naked body before I see the darkness. Suddenly, my back is pressed up against the cold metal railing, my head leaning back over twenty stories of air. "What are you doing!?"
I start to panic, but she just starts fucking me hard, "Relax, I've got a hold of you." She starts pumping so hard I can't speak, only moan and gasp. I'm holding onto her with all the strength in my legs and my arms, head nestled behind her neck as she pounds up into me.
The fear of being so close to the railing and not having control of my body only turned me on more. Then I heard the door next to me open and my eyes turned to see who it was. Jerry stumbles out onto the balcony naked. My eyes shoot wide open as he sees me getting fucked by Jill. He stands up straight and I see something shiny and silver covering his dick. A second later, Kiera walks out wearing thigh high heels and a corset only, with the largest dick I've ever seen hanging from her crotch. It's about twelve inches long and thicker than Jill's with an abnormally large head. I see it, turn to make eye contact with Jerry and see the look of fear in his eyes as she bends him over the railing and lines up her dick. She shoves it in quickly and starts ruthlessly fucking him as he cries and screams.
I watch Kiera pounding him like an animal and realize how gentle Jill is compared to her. She may be rough and hard sometimes, but it always is enjoyable. As I realized that, I started moaning and shot a load onto our stomachs, smearing between us. She only lasted a few more thrusts before she filled me up with some hot cum of her own. She stopped fucking me and gave me a lingering kiss before setting me down. She waved to Kiera before walking inside.
We laid in bed together, recovering from the sex we had on the balcony. She looked at me, staring at the ceiling, "Were you scared out there?"
I nodded my head. I could tell she was smiling out of the corner of my eye, "Good, you're so cute when you get scared I love it. You know I would never actually hurt you."
She kissed me a couple times, but I stayed quiet. "You're thinking about Jerry knowing our secret, aren't you?"
I nodded again. She straddled me and kissed me for a few seconds, "You don't have to worry about that. He may know, but he won't say anything. He's too scared, that's how Kiera works. She traps and abuses boys for her own pleasure. Not you, though. I love you."
I looked into her dazzling blue eyes, and without a hesitation, I said "I love you too." A smile like nothing else broke out on her face and she dove in to kiss me.
After a couple of minutes of making out, I stopped her, "Hey, what was that silver thing Jerry had around his dick?"
She laughed, "Kiera has him in a chastity cage so he can't get hard. She has the key to release him when she wants, but I doubt she does it often."
Fear creeped into my heart as I thought about my dick being locked away. She saw the change in my face and kissed me, "Don't worry about that, I love your cute little dick and how it squirts when I fuck you. That's how I know you're mine." We made out and fell asleep embracing each other.
I woke up to a phone alarm and went to turn my phone off, but it wasn't my alarm. So, I went back to sleep. When I woke up again, I could tell it was only a few minutes later. I felt like I had to shit really badly, but then it started moving slowly. I was starting panic thinking I was gonna shit myself when I felt it push back in and realized Jill was fucking me. She kept going slowly while she thought I was asleep. It was so soft and sensual, I loved it, but I made a mistake. I moaned. She heard it and realized I was awake and starting increasing the pace. Soon she was fucking me harder and faster than she ever had. I was gripping the sheets and biting the pillow. She would edge me and then stop almost entirely until I got soft and got my breathing back. She continued this for a full hour of sex, not letting me explode. I thought I was so close and then she pulled out completely and started stroking her cock over me, "You're my canvas, and I'm Jackson Pollock," then she erupted shooting stream after stream of white hot stickiness across my body and face. Most of it landed on my chest, but there was still more on my face than I could produce. She collapsed next to me.
After a few seconds, I asked, "Can I cum?"
She looked at me, then crawled over my dick and started sucking as fast as she could. After all the stimulation from the previous hour, it took me less than a minute to burst. She was ready, and pulled it out of her mouth and let it jet all over her face. I sighed in relief, then she laid back next to me and grabbed her phone. She opened Snapchat and said, "Babe," I turned to face the camera instinctively and she was already taking a video before I noticed. She faced the camera back to her before saying, "Love waking up with this cutie," I started to protest to her not to send it to anyone, but she already sent it to all of her streaks. She turned to me, "They're all trans and go to different schools, and then Demi, Fiona, and Kiera. You have nothing to worry about. I wouldn't hurt you, especially not like Kiera hurts Jerry." I sighed, knowing I couldn't do anything about it if I wanted to.
Over the next ten minutes she kept showing me responses from her friends. They all said, "So cute! Need me a guy to take my dick in the morning," or "Such an adorable little cumslut!"
The worst was Demi, "You should film your next session! I'd love to watch it!"
Dread creeped up from my stomach at that idea. Jill turned to me, eyes huge, smile mouth to mouth, "We have to film a session some time! It'd be so sexy! I would only let a few people see it, please for me?"
She put on a puppy dog begging face, but I wasn't having it. Her lips turned up, "It'll be one of the last things you have to do before I let you fuck me," her smile was devious.
I got excited immediately, "You still won't tell me what I need to do before I can."
She laughed and poked my nose, "That's for me to know, and you to find out, but it's settled then, when we get back, we'll set up candles, a camera, and I'll fuck you so good." She jumped out of bed before I could argue.
She got to the bathroom door, rested against the wall and pushed her hip out. She looked so sexy with her slim thick figure, tits perky, and my cum on her face. I was beginning to even like her huge dick that swung like a pendulum. She smiled and seductively said, "You're not gonna let a horny girl like me shower alone, are you?"
I rolled out of bed, noticing how weak my legs were and how sore my ass was from the morning sex. I walked to the bathroom and she let me walk in first so she could slap my ass as she walked by. I still jumped when she did it, which always made her laugh after 2 and a half months of it happening every time.
We got into the shower and she turned on the hot water. She grabbed the soap and lathered me up, I did the same and we stood there stroking each other's dicks and squeezing each other's asses while we made out under the warm water. She pulled away, "I wanna meet your mom."
I look at her bemused, "You have met my mom?"
She shook her head, "No, I've said hi as we walked past each other twice. I wanna sit and have dinner with her, so she can know who I am."
I nodded my head, "Ya sure," and tried to go in for another kiss but she dodged it.
"You don't mean that," she said.
I grabbed her shoulders and tried to look her in the eyes but she wouldn't meet mine, "Yes, I do. We can have dinner with her when we get back."
She pushed me off, "I can tell when you're lying. Have you even told her I'm trans yet?"
The truth was I hadn't. I was hoping to go my whole life without telling anyone. I hesitated then started stammering, "Uhh I uhh-"
She cut me off, "Just stop," and turned around. I tried to say something again and she turned and put a finger to my lips, "I don't wanna hear your voice, if you wanna use your mouth, you can blow me." She grabbed the shampoo and started shampooing her hair.
I felt really bad, she must've felt rejected by her own boyfriend who just told her he loved her. I dropped to my knees and started worshipping her cock, using both hands and my tongue. I was determined to make this the best blowjob I've given. Usually when she's mad, she is rough and will take control and dominate me like I'm just a piece of meat with two holes, but this time she stood still and let me do my thing without saying anything. I kept bobbing up and down her shaft while also twisting it. I paid attention to her balls and I deepthroated a few times. She paid me very little attention and just washed her hair. When she finished cleaning up, she pushed me off her dick and got out of the shower.
I jumped out of the shower and quickly got a towel to follow her. "Jill please stop. We can have dinner with my mom and I'll tell her your trans and we can have a showing of our sex tape to our friends if you want, please I'm not ashamed to be with you. I love you."
She looked at me with intense blue eyes, I wondered how they changed so easily. She thought about what to say, then just opened her towel, "You better finish this blowjob." I crawled up to her to finish the job and she stopped me, "Beg for it first. Make me believe you want it in your mouth."
She pulled out her phone and started recording. I looked up at her and then spoke as pleadingly as possible, "Please Jill, let me suck you're gorgeous cock. I love tasting the base of your cock as the tip fills my throat. I need the sweet taste of your cum on my face and in my mouth right now." She nodded and I grabbed it with both hands, licked all the way up the shaft, swirled my tongue around the tip, all while looking directly into the camera, then I plunged down all the way on it. I started sucking her off like an expert and when I could feel her about to finish, she pulled me off and blasted her load all over my face. I couldn't see, but I could feel almost my entire face being covered in cum.
She finished shooting her load on my face and said, "Don't forget to thank me."
I blindly looked to where I thought she was, and spoke, "Thank you so much for your amazing cock and your delicious load. I love having your cum for breakfast." I licked some of it off and then wiped the rest and swallowed it, making a show of it for her. When I could finally see again, I saw her putting her phone down. I hoped she didn't record that.
I finished wiping my face off and she said, "I'm not letting you back out on dinner with your mom, and we're making a sex tape for all of our friends to watch. Go finish showering so we can get ready for the game." Her voice was very authoritative.
When I got out of the shower, she was already dressed in uniform. She looked so sexy in her soccer clothes. I was putting mine on when she said, "From now on, always beg to blow me unless I tell you to blow me. And you should always thank me after a blowjob. I'd recommend giving me a blowjob at least once whenever we're with friends. Even if we're in public." She grabbed her bag and walked out the door. I could tell she was really hurt from this morning.
She would hardly talk to me on the bus ride to the game or when we warmed up. I was worried it might mess up her gameplay, but she scored 5 goals in a 5-0 win against a good team. She grinned at me as she walked back, knowing she was getting a blowjob tonight and was way ahead in the halloween bet. After the game, everyone was praising Jill and making fun of Jerry and I because they were going to get to pick our costumes. I didn't mind the harassment, I was just glad she kissed me after the game. Scoring a bunch of goals and winning seemed to help her mood a lot.
Coach let us go our own ways through the town for lunch, we just had to meet back at the fields before the second game. That meant we had five hours to explore Indianapolis.
Jill, Kiera, Jerry and I looked for lunch. Jerry didn't say much around Kiera, he'd become a broken shell of who he was, only breaking free on the field. Maybe that's why he'd been playing so well. We found a fancy restaurant that wouldn't let us in because of our uniforms, then Jill slipped the host $200 and he let us right in. As we walked to the table, Jill whispered to me, "Don't forget that I got more points than you, I would hate to cash in on that in front of the whole team." Her smile was the same evil, cunning smile that made her so sexy.
We got to a round booth in the corner and the host set out four menus and four waters. Then, he walked away. I looked at the menu a few times Jill said, "I know what I want to eat," she turned to me pointedly, "You know what you're eating yet?"
I nodded, then gulped, "Jill, may I please suck your cock for lunch. I want it all down my throat and then to swallow every drop of your creamy load." Kiera was smiling like no one else, and I refused to look at Jerry's face.
Jill nodded, "Of course you can sweetie, I was surprised when you picked up the menu, I knew all along what you really wanted."
I crawled under the table quickly, mainly to hide my shame, but I heard Kiera laugh, "He's so eager to choke on your dick, I love it." I pulled down her shirts and her dick flopped out.
I started my worshipping routine and began to quickly suck on it. I heard a waitress come to the table. She sounded confused, "Wait are you guys in the high school invitational?"
They all said yes, and the waitress asked again, "I thought it was a guys tournament?"
Jill laughed light heartedly, "Oh it is, but we both have penises, so the state rules say we have to play on the guys team even though we're girls." Jerry's leg started tapping anxiously.
The waitress was still peppy, "Oh, good for you. Can I take your order.. or, it looks like you're waiting on one more, I can come back."
Jill interrupted, "Oh no need, my boyfriend is already eating, but he will take the chicken Alfredo and breadsticks. Actually, can you make that to-go, I have a feeling he'll be eating something else until we're ready to leave."
I assumed Jill pointed to me under the table because the waitress giggled hysterically, clearly trying to keep her laughter contained, "Oh yes, I think I can do that for you, while he does that for you." More giggling from the waitress.
My cheeks were redder than ever, but also full of my girlfriends cock under the table at a fancy restaurant. I never imagined my life going this way. The rest of them ordered and I continued to slowly worship her cock under the table, teasing and making her enjoy every second of it without bringing her to orgasm.
The waitress came by and dropped off the food, she said, "Let me know when you want me to bring your boyfriends to go box. Or a few spare napkins for his knees." They all chuckled and began to eat.
They ate slowly and talked the whole meal, dragging it on. They finally finished and kept talking, Jill patted my head and said, "Keep going, I'll let you know when I'm ready."
My jaw was already as sore as it could be. It must have been an hour already. About ten minutes later, the waitress came and collected the plates and Jill said, "You can go ahead and bring out his food now, I'm just about to feed him his hard earned appetizer."
The waitress giggled as she walked away. I started deepthroating and going faster to make her finish finally and after a while she stiffened in my mouth and a torrent of cum came flooding into my mouth. I swallowed it all, gulp after gulp. Eventually, her cock stopped shooting cum in my mouth and I started cleaning her off.
I went back up into the booth, turned to Jill, and said, "Thank you so much for letting me feed on your incredible cock. I love the taste of your delicious cum."
Jill smiled contently, "Of course, anything for my little cumslut."
She leaned over and kissed me. The waitress came back to the table and dropped off my food, she looked up at me with a knowing smile, then pointed to the side of her mouth and said, "Hope you enjoyed your meal!" before leaving.
I put my finger to where she pointed and wiped up some extra cum. Jill laughed, "How silly of you to leave some cum on your face, let's go back to the fields now."