Jamie Meets Connor and The Team

Jamie Meets The Team

This story has been posted to Literotica. com with the full knowledge of the original author under my pen name, NikkijMaadison. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author. I edited this story using Microsoft for spellchecking, flagging punctuation, grammar review, and as a dictionary. I use any other suggestions only as a guide. You may discover mistakes. That will happen.

© Copyright NikkijMaadison - All rights reserved.

I took a part-time job at a private Gym in Riverdale. It was a few miles down Route One, near the UMD the campus and my off-campus house. Working at the gym gave me some 'WAM' money - walking around money and a free gym membership. I worked the front desk a few nights a week and got some studying done between work chores and member check-ins.

The Gym closed at eleven, so I would usually lock the front door, then I could go through my regular workout routine before I headed home.

This story contains sexual activities and situations between consenting adults. All characters are above the age of eighteen. Any similarity to any individual, living or deceased, or location is coincidental and unintended. The story will be told in the first person.

How I met Mike O'Malley

For one semester at UMD I was Mike O'Malley's bitch. Mike was a gym rat at the Riverdale gym where I worked part-time. Mike caught me in a sports bra and Lycra shorts one night after closing. My sissy clit that night was also sporting a silicone chastity cage. I could not hide my bulge in my tight Lycra shorts. That night he smashed my ass and rocked my world.

When it comes to anatomy, especially male anatomy, Mike is adept. He expertly knew his way around my anus. Mike's cock was the first to find my P-spot and I experienced my first full-body orgasm, and I loved it! And don't let anyone ever tell you that you can't ejaculate in a chastity cage.

And after that night, I became Mike's little sissy bitch. Mike is a married man and a gym regular. Mike's physique is ripped, with high muscular detail in the chest and legs. No body fat. His large cock is also chiseled. He's a former lacrosse player at UMD.

His sole-proprietor business provides services to the UMD athletic department, with direct contact with the teams, support staff, and players. He services and repairs all the workout equipment for the men's and women's teams. He also provides athletic supplements.

The Riverdale gym was near campus, and several UMD athletes came to see Mike for their private offseason training sessions. Mike did more than organize workout sessions for the athletes.

Late Night at the Gym

Mike's private workout session business was growing. The Gym owners were okay with it. He usually tried to schedule his private sessions during our slow periods. And his clients must be members. The owners also love the association with the UMD athletic teams. Mike has a broad reach with all UMD sports- both men's and women's programs.

Tonight, Mike introduced me to Connor, one of his UMD Athletic clients. They arrived together just before closing, and Mike, with a sly wink, asked, "Jamie, can we stay after the Gym closes to work out?

Mike helps me with my workout, too. Normally, Mike is alone but tonight was different. Connor was eye candy. He's blonde, tall, and muscular. I think he plays on the lacrosse team. He's a hottie.

I quickly responded, "Of course, Mike, I'll be here another hour, doing my workout. I just need to lock up and change." Mike and Connor were already headed towards the Cardo machines. As I locked the front door, flipping the open sign to closed, I sensed they were watching me. And they were. I gave them a big smile as I headed to the men's locker room to change out of my sweats.

My staff locker was filled with workout clothes. I always wore my sports bra and tight shorts for late-night sessions with Mike. He also loves me in chastity. He is a Pittsburgh Steelers fan, and Mike has bought me an array of chastity cages in the team colors: gold, black, blue, red, and silver. Tonight, I wore the red silicone cage under my black Lycra shorts. On top, I wore a gold sports bra.

He loved my booty, literally and figuratively. And Mike always rocked my world.

Emerging from the locker room, I spotted Mike and Connor working with the free weights. As I approached Connor, "Aren't you a cutie, Jamie? Come closer, I want to see you close up!"

Mike spoke, "Jamie, do a little twirl, and show off that perky booty of yours for Connor!" And I did. Showing off, I stumbled slightly, falling into Mike. He caught and squeezed my booty, commenting, "It's nice and tight, Jamie! All of your squats and lunges are working!"

Each of us did our sets on the free weights bench. We took turns spotting for each other. Needless to say, Mike and Connor were lifting heavier weights. I was spotting for Connor, standing over him, to assist with his lift. When he looked up, all he could see was my bulge in my tight shorts.

He commented, "Jamie, you have a nice bulge!" Looking down, I just giggled. I saw Mike snickering, too.

When it was my turn, Connor helped me on with my lifting belt. He stood closely behind me, and I pushed my booty against his body. Connor did not push me away, instead grabbed my hips, pressing his crotch into my ass. I wiggled in tighter and felt his cock growing in his tight shorts.

Connor's moved his hands almost instantly on my cock and soon discovered that my nice bulge was masked by my cage. He was instantly amused, remarking, "Jamie, what are you wearing over your dick?" He didn't wait for an answer, as he hastily pulled my shorts halfway down my thighs. He twirled me around to face him.

" Wow, Jamie, you're wearing one of those... those, those... and it's red." He squatted and used his fingers for a closer inspection. At his first touch, I slightly jerked back. He asked, "Jamie, what is this silicone thingy called?"

Before I could respond, Mike interjected, "Connor, Jamie is wearing a chastity cage on his sissy clit!" He paused, adding, "Jamie, your sissy clit looks lovely in red!"

As Connor stood, he quickly wiggled out of his shorts. His cock was massive, and as he gently stroked himself he remarked, "Jamie, I don't think my tool will fit in one of those cages, do you?" My eyes were focused on his growing cock, and Connor lifted my chin, to look him in the eyes, adding, "Jamie do you?" I shook my head sideways.

Glancing at Mike, then back at me, "Jamie, Mike tells me that you are good little cocksucker. Do you want a taste?" He gently pushed me to my knees. His cock was fat, not that long, but his chiseled circumcised head was gorgeous.

Before I can say anything, Connor remarked, "Jamie, stop staring and start sucking it!" I instantly kissed his cockhead, gently caressing his shaft with my right hand.

Mike didn't join us. Instead, he went to sit on one of the benches. He wanted to watch us. I just smiled at him. Connor pushed my head down, diverting my attention back to him.

I wanted to hold his cock tightly and just suck it as told. So, I did. My mouth and tongue devoured his pulsating circumcised cock. There was no need to tease or lick his inner thighs. I went straight to the chiseled tip of his cock, twirling my tongue all over his cock head then up and down his shaft. I repeated and repeated my tongue twirls as I pushed my mouth down his shaft. Connor whimpered, and with each tongue twirl, his whimpers increased.

But Connor had a better idea. He pulled me back up to kiss me and placed his hands on the top seam of my Lycra shorts. In one complete motion, he pulled my shorts all the way down my thighs to my ankles, stopping to reveal my cock bobbing back and forth in my cage. He was amused as he cupped my balls and caged shaft with his enormous right hand. He squeezed my cage tightly, then said, "I want to fuck you Jamie, do want me to fuck you?"

I took two deep sighs as I nodded, then mumbled, softly screamed, "Connor, yes I do! I need your cock inside me now!" I begged him to fuck me.

Mike looked at his watch, "I better get home. I performed my good deed. I knew you two would hit it off." So, Mike left early. That's okay, my attention was focused on Connor, and his attention was on me.

Connor was tall, over 6 feet. My eyes stared into his muscular chest. In comparison, Connor's statue was impressive. He towered above me. He remarked, "Jamie, Mike tells me you like hiding this girly boy persona. I like that. "

He then leaned in to kiss me full on the lips, at the same time pulling my body into his. I could feel his fully aroused cock against my stomach. I kissed him back. His hands grabbed my booty, pulling my lower torso into him. We continued kissing. His naked cock seemed to get bigger as he pressed against me. I love the feeling of his growing cock against my body.

As Connor broke off the kiss, he looked around the room. He spotted the high bench in the middle of the room. I stumbled several times, as my shorts were still dangling from one ankle as he hurriedly moved us to the bench. Connor pushed me down, and I grabbed and held tightly to the sides.

Connor spread my legs; I arched my back, pushing my booty into the air. He squeezed my chastity cage again; I was leaking profusely. I filled his hand with my precum. I heard him spit into his hand to add more lubrication to my butthole. With two fingers, he poked my puckered hole. Connor squared me up gently pushing his cock head into the crease of my anus. I screamed as he entered me, the screams turned to whimpers, and then to more whimpers.

My hip and ass movement matched his thrusts. His cock head was enormous. His girth was fat but tapered into a nice fit inside me as he went deeper into my butthole. My whimpers turned to louder moans. Connor was finding sensitive spots in my ass that only Mike has been able to explore. I gasped with each stroke. I tried to maintain my breathing. Connor's cock found my P-spot. My body began to shake all over. I grasped the bench harder. The sensation inside me was something I had only experienced with Mike.

Connor forewarned me, but it did no good. He shot his load inside my booty, not once, not twice, but three times. Each time, I screamed in pure pleasure and each time his throbbing cock shot more cream inside my canal. My body shook profusely. I was not surprised that my cock was spewing my cream all over the bench, my chastity cage and my lower stomach. It was intense. I'm constantly reminded that wearing a cage is humiliating. Chastity's release while caged is even more humiliating.

My body tumbled onto the bench. Connor held my hips to keep me from falling on the floor. Connor's cock was still throbbing inside my butthole. He slowly pulled out. My shakes became intermittent, finally calming.

Connor picked me up to embrace me in his arms. I swallowed hard, then mumbled, "Wow, that was intense. Mike's a good teacher."

I kissed Connor, and he whispered, "Yes, you can thank Mike for that! But he didn't tell me that you would experience a sissy-orgasm!"

"Only Mike and now you, Connor, have ever found my P-spot. Connor, have you ever experienced a full-body orgasm like a woman?"

Connor replied, "Yes, from Mike!" He paused, adding, "Jamie, I want to fuck you again... if you are game?" I nodded yes. He paused, "But not tonight!"

I responded, "Yes and yes, and I'm happy he introduced us."

Connor held me in his arms; he kissed me tenderly. I kissed him back. We took a few moments to sit on the bench. We were both naked from the waist down. Well, one of us was. I wanted to know more about his hunky man.

Connor Asks Jamie Out on a Date

As we dressed, we small-talked about school, UMD sports teams, and music. I told Connor I was into jazz. He mentioned that a small club in nearby Hyattsville has a jazz night twice a month.

Surprisingly added, "Do you want to go together sometime?"

He didn't ask me out on a date, but indirectly said it would be fun to go together. I'm not sure if Connor sees me as anything but a sex toy. I wanted more so I promptly replied 'Sure!"

Out of the blue, Connor spoke, "Jamie, I bet you would make a cute little girl!" he paused, then added, "Have you ever dressed femme?" He paused, grinning. He said, "Do you think you would be passable?"

I stared into Connor's eyes and confidently said, " Connor, boys make the best girls. And yes no one will know from my outer appearance that I am a chick with a dick!" I spoke in my sexiest feminine voice.

Snickering, Connor looked at me quizzically, said, "Do you want an opportunity to prove it?"

I swiftly said, "Sure, I'm game!" Connor knows nothing about my Jennifer Nicole persona.

He replied, "Wow, Jamie, one of the guys from the Athletes' Dorm is having a party Friday night at his parents' house in Potomac. Jamie, do you want to go with me as my date? " He paused, adding, "There will be a few guys and girls. Some of the women athletes will be there too."

I quickly responded, "Wow, a real date? Trust me, Connor, you won't recognize me. And when I'm dressed female, call me Jenn or Jennifer!"

He pulled out his cell, "Give me your number, Jennie!" I did. Connor leaned in to kiss me on the cheek.

Pushing back slightly, I remarked, "Connor, it's either Jenn or Jennifer, never Jennie." Connor was instantly attuned to the serious tone in my voice. I just don't answer to being called Jennie.

He instantly responded, "Gotcha, Jenn, can you give a lift back to campus?"

I replied, "Help me clean up. I must lock up and get my things from my locker, too."

It was a short ride on Route One back to the UMD campus. Tonight, it was just a drop and go. He opened the passenger door and squeezed my hand. He started to give me a soft peck on the cheek. I aggressively pulled him to me. I kissed him passionately. He kissed me back passionately. It was our first pssionate kiss.

Grinning, I said, "Connor you just smashed my ass, I want more than a peck on the cheek."

He was grinning as he stepped out of the car, adding, "I'll text you, Jamie."

I sheepishly replied, "Sure, Connor! Please don't be like other guys!"

It's Friday...

The week flew by. Connor sent me several texts. He wasn't acting like a typical college guy. He kept telling me that he couldn't wait to see me again. We tried to meet up, but our schedules didn't mesh. I did learn that Connor was a Junior from New Jersey. As a walk-on, he earned his athletic scholarship last semester. He's not a starter but a frequent midfielder substitute.

I told Naomi about him. She wants to meet him. Naomi and I do share.

On Friday morning, Connor texted me, 'Jenn, can you pick me up at 6:30? It's pizza and beer. Dress is casual, jeans and tees. Booker Roberts' parents' house in Potomac has a hot tub, too. And you promised me a perfect girl! '

I promptly replied, 'Do you want me to wear a skirt? And bring a swimsuit?'

Connor's reply was instantaneous, 'Yes and yes! See you at 6:30!' I texted a thumbs-up emoji.

I anxiously texted Naomi, she's a Potomac girl, 'Girlfriend, do you know a Booker Roberts?' She didn't immediately respond, so I got dressed for class. It was a Jamie day on the outside and Jenn underneath.

Megan, one of my sisters, was having coffee in the kitchen. I filled my travel mug and told her about Jenn's date tonight. Megan gladly offered to help with my makeup. I kissed her on the cheek as I left the house. My family is very supportive of my alter ego, Jennifer Nicole.

Hopping on the campus shuttle, I received Naomi's text, 'I went to high school with him. He's on the UMD baseball team.'

I replied, 'Connor's taking me to a beer and pizza party at his house tonight!'

Namoi replied, 'Hold On! BRB!' Her reply was prompt. 'Avery's going to that party, too. Are you going as Jamie or Jenn? I quickly responded as Jenn. Naomi returned a thumbs-up emoji. Avery Boyer is one of Naomi's housemates who knows all about Jamie and Jenn.

I had two classes and tried to stay focused. The thoughts of Connor's hard cock diverted my attention all day. I hope he was ready for round two. I was, my blue lacey boy-short panties were soaked. After my last class, I returned back to the off-campus house that I shared with my two sisters, Megan and Amanda, and Amanda's girlfriend, Aubrey, aka Cash.

Some Boys Were Meant to be Girls

Megan was lounging by the pool. I let her know I was home and went upstairs to shower. I have already had my share of waxing and laser for a young wannabe girl. A girl always has to do a little touch-up. And being soft and feminine feels so right.

Connor wanted me to be his perfect eye candy, and I have no intention of disappointing him.

Fitting into my breast forms was the next step in becoming a pretty little girl. I wanted the real skin appearance. They needed to look and feel real, plus they had to be heat-sensitive. The pair I chose is squishy with natural bounce and movement. Perfecto... I hope Connor is a boob man too.

I slipped into a red racerback plunge bralette. I wanted to wear a white tank top tonight.

Applying make-up has been a learning process. My sisters and friends have been very helpful. Megan concentrated on the contours and skin tones to blend my forms with my natural skin color. I love the transformation. I have a thirteen-step make-up routine that never fails me.

When I see the pretty girl in the mirror, I have to pinch myself, thinking, 'Who can that attractive girl be?' And it was indeed me. As Megan finished, she gave me a gentle slap on my bare booty, commenting, "You are one sexy girl, Jamie! Who's the lucky guy... or guys tonight? "

I replied, "His name is Connor. He plays lacrosse. I'm going to meet his friends for beer and pizza."

On the way out the bathroom door, she squeezed my dangling cock, remarking, Your better do something about your thingy, unless you want them to know!" As she exited my room, she blew me a kiss.

I sorted through my panty drawer in search of the perfect undie. I found it, a red C-lace string thong. My cock fit in the small pouch nicely and the wired string was firm between booty crease. Since I promised Connor a skirt, I wiggled into a comfortable red pleated mini. Three-inch wedgies completed the look.

A quick twirl in the mirror. Some boys were just born to be girls! Right now, that's what I saw in my reflection. It was me, Jamie, transformed into Jenn! In my crossbody bag, I checked that I had all my girly needs, including lube, red chastity cage, and lip gloss. Grabbing my car keys, I scooted out the door. It was a short ride to the on-campus athletic dorm.

It Was an Eye-Opening Ride To The Party

Connor was waiting for me on the front steps of the Athletes' Hall. UMD has several dorms designated for scholarship athletes. The football team is housed in Gosset Hall. Connor was staring at his watch and did not immediately recognize me or my car. Finally, through the open window, I yelled, "Connor, are you coming with me. It's Jenn, your date tonight!"

After an awkward look of surprise, he hurried to the car, sticking his head through the open window, he blurted, "I didn't recognize you, Jamie!"

Smiling, I replied, "Get in, Connor. Remember, it's Jenn or Jennifer and no last names."

He mumbled, "Sorry, Jenn, I forgot. Hell, I don't even know your last name."

Once inside the car, Connor kept repeating, "My god, Jenn, you are gorgeous!"

Giggling, I responded. "Tonight, Connor, I'm your arm candy. I might be your kinky little girl. But tonight, I'm your new girlfriend. " He leaned over to kiss me on the lips. When I kissed him back, I pulled him in closer. We embraced. My arms were wrapped around his neck. And he kept whispering, "My god, Jenn, you are gorgeous!"

I wanted his cock, but we had a party to go to, remarking, "Connor I need directions." He gave me the address and opened the navigation app on his cell phone. Off we went.

Connor placed his hand on my bare leg. My body tingled at his touch. I tried to stay focused on the road and traffic. I was in 'girly heat'. It was difficult for Connor to stay focused, too. I don't think Connor ever looked at the road, between looking at me, then back to his phone app. It was a good thing, I was driving.

He remarked, "Mike never said you were this pretty, Jenn."

Laughing nervously, I replied, "Connor, Mike has never seen me in complete girly mode. I'm just his sissy bitch fuck toy!" I hesitated, adding, "And I'm okay with that!"

He promptly replied, "Jenn, you're more than that to me."

Giggling, and trust me, I couldn't stop laughing, "Connor, since this is our first date, does that make me your true girlfriend?" We both roared in laughter. His hand was still on my bare thigh. He was unconsciously squeezing me tightly.

Connor replied, "Jenn, tonight you are indeed my girlfriend and I'm proud to say that!" He lifted my skirt to peek at my panties. "I love the lace. No cage tonight?"

I promptly replied, "Connor, it's in my purse, do you want me to wear it?"

He chuckled, "Nah, I want your cock free and available to me!"

Glancing at Connor, "Don't worry, your new girlfriend is a pushover. She puts out on the first date!"

He didn't immediately answer, then added, "Jenn, turn here; this is Booker's street. That's the house on the left.

It's Party Time... Time to Meet the Team!

There were several cars parked in front of the house. The Roberts' house wasn't a mansion, but your family has money if you live in Potomac. Booker's parents were out of town.

Connor met me on the driver's side, when we exited the car. He held mt hand and arm in the air, and said, "Twirl for me, Jenn!" I proudly gave him a perfect little pirouette. He said, "You are delicious!" I couldn't stop grinning.

As we walked up the long sidewalk, Connor grabbed my hand.

Sunny, Booker's girlfriend, greeted us at the door. Sunny's a tall blonde, who is athletic. She was wearing skinny light blue denim jeans and a UMD 'Fear The Turtle' gold tee. Before, Connor could introduce us, she said, "You must be Jenn? Connor hasn't stopped talking about you all week."

I extended my hand as Sunny leaned in to kiss. I expected an 'air kiss' instead, but Sunny kissed me on my lips. I could taste Sunny's lip gloss on my own. I love lip gloss to lip gloss kisses.

Booker quickly joined us at the door. He took the case of beer from Connor, and we joined the others in the large TV/Movie/game lounge. Connor introduced me to everybody. They are all athletic and toned. Booker, our host, is on the men's baseball team. Sunny plays women's softball. Both are in training for the upcoming season.

I met Laurence and Skylar. Laurence, a black, muscular man, is on the men's baseball team with Booker. Skylar, a very tall blonde plays on the women's volleyball team. Blue and Sara, were sitting close to each other on the large couch, two women's soccer players. Blue is a cute, short blonde, and Sara is a cute brunette.

Four people were at the corner bar. The men were standing, and the women were seated. I immediately recognized Avery, who scooted toward me from the bar stool. We embraced, and she quickly said, "Jenn, I heard you might be here!" She paused, winking at Connor, added, "And Connor's lucky to have you as his date!"

Speaking to no one in particular, Avery added, "Jenn is a good friend of my Bestie, Naomi." She pointed to Bay, sitting at the bar, she added, "Bay, Naomi, and I were on the field hockey team in high school. Bay was the only one good enough to win a scholarship."

Bay then introduced me to Eli, her boyfriend. He plays lacrosse with Connor. Avery finished the intros with her boyfriend, Kayden, a tight end on the UMD football team.

Connor just stood there, amazed that I had a connection with Avery Boyer, who knew me as Jenn. I didn't have the heart to tell him that Avery and I have sweet carnal knowledge. Connor took me aside, whispering, "Jenn, how do you know Avery?" He wasn't mad, just curious.

I wrapped my arms around his neck, pressing my body into Connor's, whispering, " I date her friend Naomi. She knows about you, and she wants to meet you."

Connor slightly pushed back; he had that astonished look on his face. Before he could speak, I interjected, "Naomi dates Jamie and Jenn. We have been known to share. Connor, are you okay with that?"

He grinned, "Do you have any more surprises, Jenn? "

I replied, "Connor, let's mingle with your friends. Let's find out! " And we did. I suspected Connor wanted to learn about me, so we returned to mingle with Avery, Kayden, Eli, and Bay. We chatted about all things UMD, or class schedules, sports, and the off-campus nightlife. The spring sports season was quickly approaching, so naturally lacrosse and baseball became hot topics.

Other than that, since I was new to the group, there were a lot of questions. I was vague with my answers. I was very generic and ambiguous. Avery was quiet, letting me answer. The beer was flowing easily, and the pizzas were finally delivered.

With each answer, someone asked another. I was happy that the pizza delivery diverted their attention away from me.

As we sat on the couches to eat, Laurence sat beside to me. Grinning, he asked, "Jenn, how did you and Connor meet?"

Connor started to speak, but I interjected, " Connor and I met at the Riverdale Gym. I work out there, and the other day, he asked me to spot for him. So, I did, and of course, flirted. And he asked me to go with him to a Jazz night in Hyattsville.

Laurence commented, I have been to that gym with Mike O'Malley, I've never seen you there. I guess my loss and Connor's gain." He paused, adding, "Who did you listen to at the Jazz Club?" It was evident that Laurence was flirting with me. Guys are so competitive when it comes to available pussy.

Connor interjected, "We haven't gone yet. I invited Jenn tonight to get to know each other better." Skylar joined us, and the talk about me ended.

The Party is Winding Down.. Then There Were Just Six

There was talk about playing 'Two Truths, One Lie', but we never started to play before some couples began to leave. Sara and Blue left first, followed by Laurence and Skylar.

Before they left, Laurence cornered me in the hallway outside the bathroom. As he caressed my bare ass cheek, he remarked, "Jenn, you're a cutie, and if you ever get tired of your gay boyfriend, look me up. I would love to tap this fine booty of yours and whatever else you're hiding in those red lace panties underneath that skirt!" My body began to shake, not from fear but excitement.

Laurence started to kiss me, but Avery intervened, telling me she and Kayden were leaving too. She added, "Sorry to interrupt, I'll tell Naomi I saw you." She kissed me on the cheek and continued into the bathroom. Laurence had already moved on, but I lingered in the hallway. I needed to compose myself before rejoining Connor. I spotted Skylar and Laurence leave the lounge room.

Avery was quick, seeing I was still in the hallway, and remarked, "Are you okay, Girlfriend?" I nodded. Avery added, " I need to confess. Bay knows that you are Naomi's boyfriend. When I mentioned Naomi earlier, she put two and two together. I'm sorry I blew your cover!"

I replied, "No worries, Avery." We embraced again.

She whispered, "Jenn, her pussy is sweet!" She added, "I hear Connor's a pretty good ass fuck! I think he likes boys and girls."

As we walked back into the lounge room together, I squeezed her booty, replying, "I know Avery!" We embraced again, and Avery and Kayden quickly departed.

If the Water's Not Hot Enough, Make it Hotter

Bay and Eli were already in the hot tub. Connor saw me coming. We embraced. "Where have you been, hot stuff?" I think he saw Laurence hit on me. I didn't want our relationship to start on a lie, so I told him

I was talking with Avery, and your friend Laurence grabbed my ass. He either assumed or I flashed him by mistake." I paused, "Or both!"

Connor did not directly respond to my comment. Instead, he said, " Eli and Bay want us to join them in the hot tub. Sunny and Booker will join us too." I extended my hand, and Connor led me outside to the expansive hot tub. I couldn't tell if Eli was wearing a suit, but Bay was clearly down to her black bra and panties. I decided not to change in my swimsuit.

Connor wiggled out of his chinos and T-shirt. He wore tight Speedos as undies. His massive cock filled the pouch. I wiggled out my red mini skirt and kicked my wedgies to the side. My growing cock was pushing the wired constraints red C-lace string thong. I'm not modest, but I clipped my white tank top. I wasn't ready to expose my breast forms, yet.

As Connor and I climbed in, if Eli didn't know I was trans, now he knew. Eli remarked, "I love the whole red package, Jenn!"

As I moved to sit next to Bay, she remarked, "Jenn, I love your lace thong! I want a closer look." I stood directly in front of her, with one hand she touched the lace, her fingers gently touched my cock. Her other hand caressed my bare cheek. She added, "I love the bare ass look, too." I whimpered.

I tingled all over as her fingers touched my body. My cock was semi-aroused. I sat next to Bay. Connor sat next to me. Bay's right hand rested on my thigh. Her other hand was now caressing Eli's cock.

Sunny and Booker joined us. They didn't bother with swimsuits. They stripped naked and climbed in. They are both toned athletes. I could get used to playing with Connor's athletic friends.

Sunny sat across from Connor. Her foot rested on his legs and eventually made its way into Connor's crotch. Each time Sunny pressed her toes against Connor's cock he squirmed. I was amused by the side show.

When you are naked or semi-naked with others, the conversation always revolves around sex. Bay remarked, "Jenn, may I ask you a personal question?" I grinned and nodded. "I know you are my girlfriend Naomi's friend, but does she prefer you in the male or female role? "

I promptly answered, "The easy answer is both. She loves being with Jameson, and she loves being with Jenn. She also loves it that I have a talented tongue and cock!" I paused, then quickly added, "I will say, she tells me she loves my tongue the best." We all giggled.

And before I could continue, Connor interjected, "I can confirm that Jenn's tongue is gifted!" The giggles turned into laughter.

A Pleasurable Dare is Not Really a Dare

Bay is not bashful, beaming, she remarked, "If Naomi was your teacher, and I know from experience, that her tongue is talented!" She paused, adding, "Does the student want to prove it?" Before I could respond, Bay pulled herself out of the hot tub, in one motion, removed her thong, tossing it to the side. She sat on the hot tub deck.

She spread her legs wide into a V, inviting me to sample her pleasures. I quickly stood on the molded tub chair to position myself over Bay's lower torso. My fingers softly caressed her fit and toned legs. Lowering my face, I began kissing her inner thighs. Bay instantly began to whimper... softly.

With alternating soft pecks and sweet licks, I gradually kissed my way up her thighs. Bay was squirming. Bay pushed a lounge pillow behind her back as I used my hands to move my arms under her booty, slightly raising her lower torso: more nibbles, more pecks, more kisses. My tongue circled the path up to her vagina. I stopped short, and Bay moaned. I raised my head to breathe deeply.

Lowering my face, I traced my tongue along her left inner thigh. Her moans grow more frequent and steady. Her lower torso moves with a wiggle. More deep breaths and Bay pulls my head back towards her pussy. "Don't tease me, Jenn, lick me!" One hand holds my head down; The other hand is rubbing her mound. Her wiggles turn to back into squirms.

Chuckling, I replied, "Bay, the student is now the teacher. Relax and enjoy!"

My attention was diverted to my booty. I could feel Eli's hands on my hips. He has positioned himself behind me. Using his legs, he spreads my legs wider. When he pulled my thong off, I could feel his hard cock in the crease of my ass.

Bay gently tapped my head, diverting my attention back to her. My eyes was once again focused on her neatly shaved pussy, with a small racing strip above her lips. Her scent is intoxicating and delicately different from my own. Her labia lips are full and puffy. Bay pushes my face down, and my tongue and mouth focus on her pussy.

Using my fingers, I softly touch, stroke, and massage her smooth pussy. Bay's body reacts to my touch. As I nibbled on her labia, I discovered a small ring extending out. My tongue licked the ring, getting a small whimper as I continued to explore Bay's sex. Bay is whimpering louder to the touch of my tongue between the folds of her vagina lips.

I insert one, then two, then three fingers, to delicately spread her lips wider with my fingers. Pressing on the front wall, Bay's G-spot bulges swelling even more as I explore her inner canal.

She now is uncontrollably squirming, pushing her lower torso from side to side. I pushed my tongue deeper between her gorgeous, bare labia lips. Her moans are now screams. She cries loudly. "Oh, oh, Oh, oh!" followed by a second round of "Oh, oh, oh, oh!" Each scream is louder than the other and loud enough to quiet the buzz from the other side of the hot tub. I paused for a moment.

Sunny, Connor, and Booker Share

Bay was my focus... not all of my focus. Eli's cock in my booty kept diverting my attention. Pleasure deserves pleasure.

It was Sunny who got the party started with her boyfriend and Connor. She pulled herself out of the steaming water, and sitting on the edge, she spread her legs wide, said, "Any takers?" I lifted my head to see what was happening, and Connor did not hesitate. He buried his face between Sunny's thighs. I love diversity in my boyfriends.

Booker, feeling left out, instantly stood behind Connor. He pulled Connor's Speedos down his thighs. Booker smacked Connor's bare ass. As Connor anchored his legs, Booker spoke, "You ass is mine tonight bitch boy!" Crossover athletes at their best!

Bay pushed my face back into pussy. "Jenn, you have unfinished pleasure here!" From then on, I only heard the sounds of pleasure coming from Sunny, Connor, and Booker.

Bay Wanted More

Bay's hand on my head brought my attention back to her pussy. My tongue again parted her labia lips. Bay is indeed wet now. She smells and tastes divine. I suck her juices out, swallowing as much as I can. Bay's whimpers quicken yet again, becoming deeper and faster.

I took several deep breaths blowing warm air into her soaked pussy. She raised her voice, softly between whimpers, "Jenn, don't stop!" I didn't. I know what I am doing. I ran my tongue up and down her labia lips, blowing more warm breath into the soaked area. Bay is squirming uncontrollably now.

My tongue pushed deeper between Bay's moist labia lips, and I could feel her body tense with the touch of my rotating, firm tongue. I keep moving my tongue from side to side, alternating with up and down strokes. Bay's whimpers become quicker in response. She was quickly on the edge of round two.

I feel her hand above my head, rubbing her clitoris. I place my fingers on top of hers, trying to replicate the movement of her fingers. Feeling her lower movement pushing her crotch into my face, I teased her with my tongue, slowly dancing around her clit. She placed both hands directly on my head, gently pushing me down.

With my tongue on her clit, I build a sensation. She started with more "Oh, oh, ohs." Her whimpers quickly turned into louder moans. All I could hear between moans was Bay repeatedly calling me. "You little Bitch, Bitch, Bitch!" Her crescendo is now loud again. My body began to tingle. I was fulfilling the dare.

The Teacher is Not Finished!

Eli's hands held my hips tightly. His cock was still pressed against my booty's crease. He has not entered my puckered hole. He was mesmerized by Bay's reaction to my tongue and fingers.

I wanted Bay to sing my praises, so I buried my head deeper between her thighs. Using the tip of my tongue, I widen her lips, feeling more juice on my face and chin. I push one finger inside Bay's vagina, looking for that special spot inside. I insert the second finger. Bay takes control of my hand, pressing my fingers up the vagina's inner wall. Déjà vu! But I wasn't done; she wanted more.

The rhythm of her moans increases as I exert more pressure on the inside walls. More moans. Her sound guides me. My head is buried in Bay's thighs, and my tongue and fingers are pushing her sweet spot. My mouth is drinking her sweet juices. It puffs again as I continue to put more pressure on that spot. I feel her body tighten and then violently shake.... again. She pushed my head deeper into her pussy, and her body was spasming. I could barely breathe as her thighs press against my head.

More loud screams from Bay, then calm. She was soaking my face, spurting her juices all over; there was so much fluid that I gagged. With her thighs, she again squeezes the side of my head, and her body shakes more intensely. She bellows, "God, Yes, Yes!". She has no control over her own body. My mouth and fingers were in control. I lost count of her orgasms. Was it now three, four, five, or six?

At that moment, I noticed her body relax and find a blissful peace. Bay fell back onto the deck. I wanted to cuddle with her, but Eli's hard cock distracted my focus from Bay back to my ass.

Eli Seizes The Moment

Feeling Eli's hard cock in my crease, I instinctively pushed my booty into the air. Eli helped anchor my legs wider from my knees. I arched my back. I feel sexy in this position, but I also know from experience that his penetration will be deeper and less painful. I could feel his cock harden in the crease of my ass, so I pushed my ass out to meet him.

I am craving his cock in my ass. I wiggle my hips not only to get his attention but to help loosen up my body. I hear Eli nervously laugh as he watches my hip movement. He pushed my head down. I arch my back, pushing my ass out further. His cock is still dangling against my booty; it feels more aroused than before. My willingness has stimulated him. I am ready; so is Eli. But Eli is teasing me.

Relaxing my butthole, I focus my mind on accepting his cock inside me with little or no pain. Eli pushes his body further inside my spread legs and thighs. Using his pre-cum and saliva, he starts lubing my butthole.

He pushes in slowly, pumping his cock into my puckered hole. I scream, then scream louder again. It hurt. But fuck, it was hot. Eli's cock inside me feels massive.

I pushed back to meet the rhythm of his thrusts. My screams turn into frequent whimpers, and I feel his balls bouncing off my ass. With each thrust, I try to take a long breath. Thrusting and wiggling my ass onto his cock, I am twerking at my finest. "Keep fucking me," I whispered to myself. "I need this. I want this!"

Eli slid his cock deeper and deeper inside me. Much deeper than I thought was possible. He repeatedly smashed my ass. His cock began rubbing and thrusting against my P-spot; I was out of control. That friction was too much. My prostate was now stimulated. Eli squeezed my balls and pushed his fingers against my outer P-spot. It was apparent that Eli was under Mike's tutelage, too.

My entire body was now shaking. I cried out in pain and pleasure. I came oh so hard. I kept cumming, one spurt followed by another. My cream was floating on top of the water. "Oh shit," I whispered. My orgasm was powerful.

Eli was not finished with me. His perfectly timed thrusts continued to push deeper and deeper inside me. He braced himself with his hands on my hips so he could thrust even deeper. I felt a load of cum enter my ass. My muscles tensed again as Eli deposited several more loads into my butthole. I felt pulse after pulse, going on and on. This time, he screamed. His cock was throbbing inside my butthole. It's a fantastic feeling.

It felt wonderful to have my insides so full of his semen. I loved how messy it felt and couldn't wait to feel it dripping out of me later. His load seemed heavy.

I fell forward; Eli pulled his throbbing cock out of my butthole. Suddenly, my body felt empty. My orgasm was powerful. My body was still trembling; my legs felt unsteady. I held onto the edge of the hot tub wall.

Eli stood behind, taking deep breaths. He was spent. He whispered, "Wow, that was terrific!" I'm sure he was talking about his orgasm. Eli climbed out of the tub, leaving me alone with his girlfriend, Bay.

Bay Had Watched Her Boyfriend Smash My Ass

Bay sensing my emptiness pulled me towards her to join her on the hot tub deck. We were the only ones remaining in the hot tub. She remarked, "Jenn, don't pay any attention to him. Eli can be insensitive, and I know he's embarrassed by the pleasure you gave me! He only thinks with his cock."

She held my chin, kissing me gently. We exchanged soft, gentle kisses, and my heart began to race. Her arms were around my waist, holding me tightly against her chest, and I was holding her body tightly against me.

Our kisses linger on, filled with warmth and connection. She tenderly draws my upper lip into her mouth, breathing warm air into my open mouth. As I turn my head just a bit, I gently suck on her lower lip, feeling the heat building beautifully between us. We share a moment of sweet release--she lets go of my lip, and I gently release hers.

Bay glides her tongue along the edge of my cheek, and I let out a soft moan. She withdraws slightly. It's my turn; I gently kiss my way to her right earlobe, softly kissing and licking the lower lobe. As I softly blow into her ear, I gently nibble on it. I can feel the warmth radiating from her body.

I push back slightly, moving my hands up her body and placing them gently on her head, tilting it to the left. I softly run my fingers, delicately tracing her earlobe and then smoothly down her neck. I am not rushing; I take my time. I follow my fingers with soft kisses and nibbles.

Bay whimpers and then breaks the silence, "Jenn, your tongue is delightful; you do pleasure a pussy like a true woman! You are indeed gifted. Your tongue is sweet!" I was speechless. We look into each other's eyes. I am in awe of her smile and beauty. And I wanted more.

Then Bay added, "When will I experience the Jameson side?"

Before I could answer, Eli returned. He was fully dressed. She remarked, "Bay, I need to return to campus. I have a paper due on Monday!"

I stood and quickly left the hot tub deck. Bay and Eli needed time alone. I needed to clean up anyway.

The Party's Over and Back to Campus

We were all exhausted. It was already after midnight. I was sad that the party was over. I met some new friends. Before we left, I exchanged cell numbers with Bay and Sunny. I wanted to see them both again. You know girly things. I'm game, if they wanted to invite their boyfriends, but my attention was now on Connor.

We all dressed and I removed my wet tank, finally, bearing my breast forms. Everyone wanted to squeeze my boobies. Eli admitted that he thought they were real under my tank. Connor just giggled. I looked but couldn't find my thong.

Sunny said she would look for it. She handed me one of her T-shirts. It was so big on me, I didn't need to put my skirt back on.

Before we left, Sunny had disappeared. She went to bed exhausted. Bay and Eli left when we did.

On the way out, she asked, "Jenn, I have your lace thong or rather Eli does. Can he borrow it?" I smiled and nodded, and she added, "Eli has a panty fetish. He's actually wearing it now." I could see Eli smiling over her shoulder.

We hugged again, she remarked, "Jenn, let's meet for coffee on Sunday. I'll text you." She squeezed my bare booty.

On the ride home, Connor and I rehashed the entire evening. He's not the jealous type. He commented that he wanted to meet Naomi, too. He said I was 'perfect trouble', or as he simply said, "Jenn, you are a good girl who knows how to be bad!"

As we neared the campus, I invited Connor back to my house. He readily accepted, and we stayed up all night and day. We didn't leave my room until late afternoon. And we didn't get much sleep. I love having a hunky man in my bed.

Epilogue

I also became a lacrosse fan and attended many home games that semester. The lacrosse team always partied together after their home games. Lacrosse players are a close-knit team. I always went as Connor's date, and I loved the attention the partygoers gave me.

Bay and Eli were always at the parties too. I was always happy to see Bay, but Eli was indifferent towards me. The Sunday meet-up with Bay for coffee was just the beginning of our frequent solo hook-ups. When we were together, we never talked about Eli. I understand that they are no longer a couple.

Sometimes the parties were at Mike O'Malley's house with a pool. I finally met Mike's wife, Nora. She's a hottie, short, blonde, and stacked. I loved flirting with her. She said Mike talked about me all the time, but she never mentioned if she knew I was his sissy bitch.

Connor and I were an item that semester, and more than once, I shared Connor with Naomi. Connor slept over at my house a few times a week, and if he wasn't there, Naomi was.

At the end of the semester, I moved back to Annapolis for the summer. Connor Walker went home to New Jersey. He visited me a few times at the Madison Compound. My mother adored him. He didn't return to UMD in the Fall. He transferred to a smaller nearby lacrosse school to be a starter.

When his college played at College Park, I went to the game. He stayed with me for a few days. The sex was terrific, but the overall attraction was not there anymore. I think Connor has a new friend at Towson. He didn't say!

During the Fall semester, I didn't return to work at the Riverdale gym. I also did not see Mike sexually again. From time to time, during the spring lacrosse season, I would see him at a game. To this day, I still enjoy watching a lacrosse match.

And yes, Laurence stopped by the Gym. And yes, he did discover what I was hiding under my skirt. But yes, there's a but! No pun intended. There is an adage that applies to Laurence: 'There is no such thing as bad sex, sometimes it's just better with others.' Laurence did not rock my world.

To be continued

Mike O'Malley was briefly introduced in the story 'Chastity is a Confusing Kink' in the 'Discovering Nikki Madison' series. Connor and the athletes will appear again in the 'Jen Nicole's College Years' series. Please tell me who you want to learn more about In the comments.

As always, your comments and feedback are valuable. I sincerely hope you are enjoying Jennifer Nicole's Kinky Adventures. Please take a few moments to share your thoughts in the comments section. I always want to improve my stories and genuinely need and want your feedback.