Confessing to My Girlfriend Pt. 01

This is a true story of how my girlfriend found out I was a sissy. All participants are over the age of 18. Names have been changed for privacy. If you haven't read Skipping Practice, I highly recommend you read it first!

It was warm and sunny Saturday afternoon in late spring of my senior year of high school when my life changed forever. My girlfriend had invited me over to have a cookout with her family. I pulled into the driveway just as her dad tossed some steaks on the grill.

"I think she's around back," he said as I walked up the driveway. Giving him a wave, I walked around the side of the house to find my girlfriend Abby.

As I came around the corner, I saw Abby laying on a blanket in the yard and attempting to get a tan. She was wearing a green bikini top and cutoff jean shorts. Her massive tits were stretching the thin fabric to its limit. "Holy fuck," I mumbled to myself.

Abby and I had been together since our sophomore year. She was 5'1" and a little chubby, with curly blonde hair, a thick ass, and massive watermelon-sized tits. Her tits were slightly saggy with giant light brown areolas that were easily 4-5" in diameter. The first time I saw them I realized that I had a kink for girls with big areolas. On top of all that, she was an absolute freak in the bedroom.

As I approached she waved and called out, "Over here! Dad just put the steaks on! Come join me!"

"Those steaks smell great," I said as bent down and gave Abby a quick smooch. I pulled my shirt off and lay down next to her, using my balled up shirt as a pillow so I could prop my head up for a better view.

I openly stared at Abby's chest, where a war was being waged between her massive tits and her tight bikini top. The tops of her huge areolas were ever so slightly peeking out from behind the fabric. My gym shorts made it easy to see that the scene before me was clearly turning me on.

"Yeah I know my top is too small, but it's the only one I could find," Abby said looking at me, "Besides...I think "he" likes it." Before she finished her sentence I felt her hand rubbing my cock through my shorts. It only lasted a few moments before she pulled hand away saying, "Save it for after dinner my love."

"Then pull your top up because your nipples are showing," I said readjusting myself.

"Whoops," she said laughing, "I hope they haven't been sticking out for very long." She adjusted her top, and rolled over onto to her stomach, propping herself up on her elbows and asked, "Do you have any plans after dinner?"

"Well other than fucking you...nope I'm entirely free," I replied.

Abby rolled her eyes saying, "Bethany's parents are out of town, and she's having a few people over. Can we go over for a bit?"

From my previous experiences with this exact situation, I knew it was going to be Abby and handful of her friends, and not the party I was hoping for. Before I had a chance to respond, Abby's mom opened the back door and told us dinner was almost ready.

"Great!" Abby said, "It'll be fun I promise." And with that she got up and started walking towards the house. I stood up and put my shirt back on and turned to follow her. To my delight, the bottoms of her ass cheeks were sticking out her cutoff jean shorts. "If I'm going to hang out with her lame ass friends tonight then I'm fucking her ass when we get home," I thought.

The sight of her ass cheeks sticking out as we walked inside sent blood rushing to my cock. I tried to adjust myself before stepping inside, but the outline of my 8-inch was clearly visible against the thin fabric of my gym shorts. Luckily, there was maybe 10 feet of hallway between the back door and the kitchen so I quickly headed towards the dinner table.

Right as I turned the corner Abby's mom was turning around after setting something on the table and she ran right into me. "Oh! Sorry I didn't see you there!" she said as she stepped back and looked at me, "No worries! Have a seat!" She very clearly felt my dick when she ran into me, and I saw her eyes dart down before looking up at me. "Sorry about that Mrs. M," I said nervously as I sat down. For a second there I thought I was fucked, but she just smiled and sat down across from me.

Abby took a seat next to me. As she sat down she put her hand on my lap and rubbed my now rock hard cock through my shorts. Like I said earlier, Abby was a freak and one of her favorite things to do was play with my cock in front of her family without getting caught. So there I sat...eating steak with her mom, dad, and sister...engaging in conversation...while having my girlfriend play with my rock hard cock periodically under the table. Just a normal night. Dinner progressed and when it was over Abby's mom got up and started to clear the table.

"I think we're going to go over to Bethany's for a bit. Is that alright?" Abby asked as she slipped her hand up the leg of my shorts and exposed the head of my cock.

Just as her fingertips reached the tip of my cock, her mom suddenly turned around saying, "That's fine sweetheart. Just be back by curfew." Abby quickly pulled her hand away, but it was too slow, and I saw her mom's eyes glance below the table before turning back to the sink.

She had clearly caught a glimpse of my rock hard cock sticking out from the bottom of my shorts, but surprisingly she didn't skip a beat. I got up and went to the bathroom while Abby ran upstairs to change. As we headed back through the kitchen to the back door, Abby's mom smiled and said, "Have fun!" As I walked past, she glanced at my crotch and gave me a smile.

"Well, you're mom just saw my cock," I said as soon as we got into the car.

"No she didn't," Abby said dismissively, "If she saw it don't you think she would have said something?"

"No I'm pretty sure she did," I replied, "She looked down at my crotch as we were walking out and then gave me a weird smile."

"Well if she did then she clearly didn't mind," Abby said with a laugh, "Now where were we..." Abby grabbed my cock through my shorts and said, "I know you were horny at dinner...and I know you REALLY don't want to go to Bethany's...so how about..." Abby said as she casually pulled my cock out from my shorts, "...I reward you..." Just as she finished her sentence, Abby leaned over and engulfed my cock in her mouth. After a few swirls of her tongue around the head, she opened wide and took my cock as deep in her throat as she could before slowly pulling it out and repeating the process.

"Oh yeah," I said struggling to focus on driving, "That feels amazing...should we pull over?..."

"Hmppphhhuh. Yoummmppphh have to cummupphh fast," she replied with my cock still in her mouth. The next time my cock went into her throat she picked up the pace and starting bobbing her head up and down on my 8" cock.

After a minute I could feel myself getting ready to explode in her mouth. I couldn't help but think about sucking my buddy's cock a couple weeks ago. We had decided to skip practice, and we ended up back at his house. We got caught in a thunderstorm and were soaked. After we stripped out of our wet clothes, one thing led to another, and before I knew it I had my first experience with gay sex. I even tried on one of his mom's thongs and let him fuck me like I was his sissy bitch.

I had recently discovered sissy porn, and I absolutely loved the feeling of his cock in my pantied covered ass. Abby and I had plenty of anal play experience, but that was the first time I had ever been fucked by a real cock. I hadn't accepted that I was a sissy so I kept that secret buried. Imaging Jay's cock going in and out of my ass was enough to push me over the edge.

"I'm...gonna...cum..." I moaned. I felt my orgasm hitting as spurt, after spurt, of my warm cum flooded Abby's mouth.

"Mmmmm," she said as she swallowed my cum. Finally I stopped cumming so she took my cock out of her mouth and sat back in her seat. "Holy shit! That was a lot of cum!" Abby said wiping cum her mouth, "Now I don't want to hear you complain about going to Bethany's."

"Just be happy I didn't crash," I replied as we turned down Bethany's street.

As I predicted, when Bethany said she was "having some people over" she really meant Abby and her best friends Emily, Megan, and Kristen. And of course I was the only boyfriend that got dragged along. "This is going to be so much fun," I said sarcastically as we walked inside.

The next hour or so was as uneventful and lame as I had predicted. Bethany raided her mom's wine collection, and the girls were starting to get a little tipsy. We were all sitting in the living room when out of nowhere Emily looked right at me and said, "I'm totally jealous of your hair."

Puzzled I replied, "Huh?" I had been growing out for over a year at this point. It was light brown, shoulder length, and wavy...basically think of a hair product commercial. Abby was constantly playing with my hair and telling me how jealous she was.

Emily stood up stumbling a little bit, and walked right over to me on the couch and started running her fingers through my hair. "I mean holy shit! It's so soft and thick! What products do you use?"

"Huh? Products?" I said trying to act confused.

"Oh he uses all kinds of stuff," Abby chimed in with a laugh, "he probably has more hair products than most women!"

"Hey now," I said turning red,"...mostly I just use regular conditioner."

"Oh come on! It's just us girls. We promise we won't tell," Emily shot back with a smirk.

"Well," I said hesitantly, "Other than shampoo and conditioner, I always use a clarifying shampoo once a week, a daily leave in conditioner and moisturizer, and aloe every couple weeks."

"Holy shit! You use more products than probably all of us combined!" Emily shrieked. All of the girls burst out in laughter at my confession.

"Sounds like you're jealous," I said as my cheeks turned red.

"Go run your fingers through his hair," Abby said still laughing.

I was clearly embarrassed, but hopefully they would just touch my hair and we could move on to the next topic. One by one, they all came over and ran their fingers through my hair. Kristen went last and while she was playing with my hair she turned her head to the other girls saying, "We should totally give him a makeover! He does have nice hair, but he needs a little makeup and maybe a new outfit."

"YES!" Abby shouted and jumped out of her chair while all the other girls started cheering. "We need more wine," she said with pure excitement. "Bethany take him with you and find him a cute outfit for him to wear. We'll get the drinks and snacks," she said as her, Emily, and Kristen headed towards the kitchen.

Bethany gave me a devilish grin as she grabbed my arm and pulled me with her. "I bet we can find something that fits you in my sister's room," she said as she led me upstairs.

Out of all Abby's friends Bethany was definitely the hottest. She was 5'9" and maybe 140ish pounds. Her tits were probably a small C-cup, but the best part of her was her absolutely huge ass. She had platinum blonde hair with a bob cut that screamed, "I'm the dominant one" when she had her hair up.

Tonight she was wearing sweatpants, but I could easily see the outline of her perfect ass. As we headed up the stairs she grabbed the handrail to steady herself. This caused her t-shirt to hike up, and reveal a black thong poking out of the top of her sweatpants. By the time we got to her sister's room I was halfway to being hard.

"Let's see what she's got," Bethany said as she opened her closet. I adjusted myself in an effort to hide my growing bulge as she rummaged through the closet. "Here! This is perfect!" She turned around holding a black pencil skirt, a white spaghetti strap tank top, and a bright red sheer blouse.

"Uhhhhh...a skirt?" I said taking the clothes from her.

"Stop being such a sissy," she said moving to the dresser, "just try it on." My head snapped up...wait...did she just call me a sissy? My heart skipped a beat. She was busy digging through the dresser drawers so I figured it was just a coincidence and dismissed it.

Holding up the skirt I realized it wouldn't fit over my gym shorts so I turned around and slipped them off. As I pulled the skirt over my butt I felt a suddenly rush of blood to my already engorged cock. "Fuck, fuck, fuck!" I thought. I took a deep breath to calm myself down, and did the best I could to hide my growing erection. I prayed nobody would notice.

"It looks like it fits from the back," Bethany said snapping me back to the moment, "Turn around and let's see the front."

"Here we go," I thought as I turned around to face her. I watched as her eyes slowly looked me up and down.

"Hrmm it looks good," she said coming closer. She used both hands to adjust the waistband. "Let me straight it out for you," she said dropping to her knees. I looked down and saw a bump on the front of the skirt as my cock started to betray me. Her face was inches away from it, and I was sure she saw it as she adjusted the skirt.

"There!" she said with the slightest grin as she stood up, "let me grab the shoes." She didn't say anything though so maybe I was in the clear. Bethany handed me a pair of red heels and I turned around to head downstairs.

"Hold on a minute," she said. Nervously I turned around. She had that same devilish grin from earlier. In her left hand she was holding the red heels, but in right hand she was holding a matching red thong with little black bows on the front. It was lacy and practically see-through in the front, with a thin strip of fabric in the back. Instantly the bulge in my skirt grew as I stood there terrified.

"I think this will go great with your outfit," she said putting the shoes and panties in my hands.

"I must confess...I have been fantasizing about this for a while now," She said looking me directly in the eyes as she ran her fingers through my hair, "I wasn't sure you wanted it until you tried the skirt on," I felt her rub my cock as it strained against the dress, "And I knew you were a sissy."

"Bethany...I...Abby doesn't know..." I managed to stammer out as she continued rubbing my cock.

"Shhh...don't worry about that sweetie...It'll be our little secret," she said giving me a kiss, "We don't have much time so hurry up and put those damn panties on." She was right. We had only been upstairs a few minutes, but I knew I had to hurry.

Bethany took a step back and placed her hands on her hips to watch me change. I hiked my skirt up and pulled my underwear down, my 8-inch cock bounced as I sprung it free.

"Oh wow," Bethany said biting her lip, "I didn't realize it was that big...it's good that you shave...a good sissy always keeps her clit hairless." I flashed her a smile as I stepped into the panties and pulled them up. I was easily able to get the back adjusted, but my cock was too big to fit in the panties.

"Here hunny, let mama help you with that," Bethany said as she knelt in front of me. She wasted no time, pulling my panties to the side and taking as much of me in her mouth as she could.

Looking down, I watched as she stroked and sucked me at the same time. It was at that moment that I embraced my inner sissy, and I didn't care if Abby found out. "Yes mama...suck my big clitty," I said in my most feminine voice. Bethany looked me right in the eyes and gave me a quick nod of approval.

She paused, taking my cock out her mouth saying, "Hold on. I don't want to get messy." She ripped her shirt and bra off in one motion. She had torpedo tits with pink areolas that were large and puffy. I reached down to grab them, but Bethany smacked my hand saying, "I'll tell you when you can play with mama's tits. Do you understand?"

"Yes mama. I'm sorry...I just couldn't help myself," I said timidly.

"Good girl," she replied as she grabbed my cock and got back on her knees. "Mama will let you play later." Bethany resumed her kneeling position and grabbed my cock. "I really don't want Abby to walk in so we need to speed things along." Part of me hoped she would walk in to be honest.

She spit in her hand before going back to sucking my cock. I was slightly confused, but then I felt her wet finger rubbing circles on my asshole.

"Just relax and mama will show you how to play with your sissy pussy," Bethany said in a soft voice. One of her wet slippery fingers teased its way inside my asshole. I let out a soft moan as she worked it in and out. She chuckled saying, "I see this is the first time you've had your pussy played with." I felt a second finger squeeze inside me.

She picked up the pace and starting fingering my ass faster. Abby had fingered my ass during a blowjob a few times before, but nothing compared to this. I felt a massive orgasm building inside me.

"I'm close," I squeaked out. Bethany took my cock out of her mouth and started squeezing my balls with her other hand. Before I could protest she shoved another finger inside my ass, stretching my tight sissy asshole. "Cum for mama," she said as she opened her mouth wide just inches from my cock.

"Oooohhh I'm cumming!" I cried out. My legs shook as I flooded her mouth with cum. It was one the most intense orgasms I've had ever had, and Bethany swallowed gulp after gulp.

After my balls were spent she stood up and kissed me, shoving her tongue into my mouth. I could taste my cum as our tongues swirled.

"That's a good little slut," she said breaking off the kiss.

Before I could say anything we could hear footsteps going up the stairs. Panicking, I immediately pulled up my panties and skirt. I barely got the skirt on as Abby appeared in the door saying, "Ooohhh I see you found an outfit!"

"Yes we did," Bethany said giving the bulge in my skirt a light squeeze as she walked past me, "show them your new look!"

The girls were giggling as they got into position to wait for my big reveal. I tried to adjust myself to hide the large bulge in the front of my skirt, but it was no use. My cock was still slightly engorged despite cumming twice already. "Fuck it," I thought trying to reassure myself, "they've probably had enough wine that they won't even remember tonight."

I took a deep breath and turned around. "Don't you think I just look fabulous darrrrrling," I said in my best girl voice.

There was a brief pause, as they looked me over before Abby shouted out, "I love it!" She and Bethany were lying on the bed, propped up by pillows.

"You totally nailed the secretary look!" said Kristen. She was lying on her stomach at the foot of the bed. I could see her eyes fixated on the bulge in my skirt.

"Boohoo I love that blouse on you," Emily chimed in. She was sitting in chair next to a vanity. "Hold on," she said as she rummaged through the makeup on the vanity before grabbing a tube of bright red lipstick. She jumped up and opened the lipstick as she walked over to me.

Laughing she said, "I might be a little drunk...hold still." She opened the lipstick and applied to my lips. "Now rub your lips together," she said taking a step back and quickly glancing at my bulge. I did as she instructed. "Hang on there's one spot," she said getting close enough for her tits to bump into my stomach.

Emily was probably 5'6", brown medium length hair. She was pear shaped with small tits, thick thighs, and a big ass. Definitely the least attractive of the group, but from what Abby told me, she is wild in the bedroom.

"There," Emily said, "Perfect!" I felt her hand brush against my bulge as she put the cap on and returned to her seat. I don't think it was intentional, but I felt my cock grow slightly, making the bulge even more noticeable.

The girls were sipping wine and giggling amongst themselves as I blew kisses and struck poses in my new outfit. They responded with cheers and catcalls. With the exception of Bethany, I could tell that the girls were wasted at this point. They were definitely too drunk to remember this so I gave them a show. I danced around for a bit before posing with my hands on my hips saying in my girlie voice, "Well ladies. I must say that I am clearly the sexiest bitch in this room."