One Sexy Halloween Costume Pt. 02

This is a true story. This is the second and final part of the 2 part series. Part 1 is not necessarily required in order to enjoy part 2.

One Sexy Halloween Costume-

It was now Thursday, the day before Halloween. I woke up right after Gabby left for work, and noticed my rectum felt swollen from the butt plug the night before. I decided to skip my morning workout and went straight to my laptop. Through my research I found out what I experienced last night was called a ‘prostate orgasm’, ‘hands free orgasm’, or ‘sissygasm’. Different sites had different names for it and I went down a rabbit hole exploring different vocabulary. I found people that have had this kind of orgasm referred to their butthole as a ‘boipussy’ and their penis as a ‘clitty’. For a lot of these people, they had been chasing the elusive hands free orgasm for years, but most are unsuccessful. So the fact that I achieved it accidentally my first time seemed to make me some kind of a prodigy. There also seemed to be a general consensus amongst those that have achieved it that it was a ‘point of no return’ eventually leading to more... This frightened me, I definitely enjoyed my experience, but I’m not gay, I love having sex with Gabby. I’ve only been ignoring my penis because I want to be completely ready to fuck Gabby tomorrow night on Halloween.

I shut the laptop, and tried to forget about it. After all, I had to use my last tanning day, get one last ankle weight workout in, and finish up the house chores. With the way my butthole felt, I didn’t even try to wear the butt plug during the day.

When Gabby got home I had dinner all ready made. A light tofu dish that I found on one of the fitness accounts on instagram recommended for booty building. Over dinner she let me know the plan that her coworker Amy put together.

The plan was that I would take Gabby to work tomorrow, and she would catch a ride with Amy afterwards. Since Amy is hosting the pre-game, Gabby would just get ready there, and when I was ready I would just Uber over so we wouldn’t have to worry about the car for the night.

“But I thought we would get ready here together,” I said, “I thought you would do my makeup?”

She replied, “Hmm, I didn't even think about doing your makeup. How about you just put your costume on and then come early and I’ll do it there?”

“Ok, but don’t you want to see me in my costume before everyone else?” I asked, not liking the idea of revealing my new body to others before getting her approval.

“It will just be Amy and I when you get there babe,” she said “everyone else will be getting there at 9pm.”

"Ok, but don't you want to see if you even like my costume?" I asked.

She looked a little confused and said, "I'm sure I'll love it"

I dropped it before I gave too much away. Considering this was going to be my first time wearing my very own girl outfit in front of people since I started cross-dressing 8 years ago - this was a big deal, but I needed to play it cool. I was really excited to open my packages that night too since I planned on showing Gabby my costume, but decided against it. We cuddled on the couch and watched a movie before going to bed.

The next day I woke up immediately when the alarm went off.

Today is the day, Halloween, what I've been preparing for all month. I got up, drove Gabby to work, and kissed her goodbye. Overflowing with excitement, I rushed back home to begin my transformation. I ran upstairs and started tearing open all of my packages, and carefully laying each piece of my outfit out on the bed to wait there for me as I showered.

I got in the shower and sat down as I lathered Gabby's shaving cream over my chest, stomach, and armpits as the warm water ran down my tanned legs. I gently shaved each section of my upper body until they were hairless and rinsed off before starting on my pubes. I’ve shaved my balls numerous times, but shaving my ass and around my butthole was very meticulous and took some time. I finished by shaving all the way around the top of my thighs. I was too nervous to completely shave my arms and legs in case sharing my feminine side with Gabby tonight didn't go as planned, and I needed some masculine features to fall back on. Plus, my outfit had stockings and long sleeves that would hide the remaining body hair.

Lastly I shaved my face and I was now completely hairless minus my limbs. Now it was time for the final touch. I reached for the industrial grade prosthetic adhesive and applied three coats over both nipple areas of my chest letting them dry in between each coat like the instructions directed. I then peeled off the plastic film on the back of each B-cup silicon breast and stuck them onto my chest pressing firmly for a few minutes. When they felt firmly glued I pulled my hands off. It looked a little strange, somewhat wider than I pictured, but I now had my very own set of tits! I gave a little shimmy in the mirror and confirmed that they weren't going anywhere without some strong rubbing alcohol. Lastly I grabbed Gabby's scented lotion and applied a coat over my entire body to retain the moisture from the shower.

I gleefully scampered back to the bedroom to do what I've been looking forward to for so long - see how my new outfit looks on my new body :)

I looked down at the bed, took a deep breath, and grabbed my light pink cotton thong with floral lace decals. I sat at the edge of the bed and stepped into my panties pulling them up across my soft legs and positioning them right inside the defined “whale tail” tan line positioned above my cheeks. I then did a quick squat to get the thong deeper into my butt crack and unfortunately this made me rock hard. Luckily I opted for a smaller size thong, so it kept my clitty pressed firmly against my stomach. Ignoring my erect member, I wrapped the matching 36B light pink lace bra around my stomach to clip it together and slid my arms through as I pulled it over my silicon breasts. The bra inherently pushed my fake boobs together which consequently made a natural looking crease in the middle of my real chest by bringing my adhered pecs together with them.

Before putting on the rest of my outfit I decided I should probably do my nails first. I grabbed the light pink nail polish, acrylic nails, and threw on one of Gabby's silk nighties for the fun of it. I set up shop on the couch downstairs and put a youtube video on the TV titled "Cross-dressing in Public". I started with my toenails and realized this was going to take awhile. I've never painted my nails before, and there was definitely a bit of a learning curve. After youtube cycled through a couple of related videos I finished up my toes and began glueing a fake coffin-shaped nail onto each finger. After a few more videos I finally finished my nails and let them dry. Oh my goodness, I was thoroughly impressed with how dainty and pretty they made my hands and feet look, and once again I felt my clitty trying to get me to break our no-touch agreement. As a result, I quit admiring my manicure and pedicure and ran back upstairs to finish getting dressed.

Now that my toes were painted I was able to put on each black thigh high stocking over my tan legs, and then slipped on the light pink lace garter above my hips. I managed to clip each garter clip to the top of the stockings, but made a mental note to do this step before I put on fake nails in the future. Ughhh I hope I can do this again in the future. Next I put on my heels that I’ve become so comfortable walking in the last few weeks, stepped into my black flowey skirt, and pulled it up over my hips so that the bottom of the skirt sat just below the top of my stockings. I couldn’t resist doing a quick twirl in it, I’ve really become quite empowered wearing heels, and the skirt totally amplified it. Finally I slipped into my new top and positioned it around my boobs so that my prosthetics were hidden, and the only cleavage showing was the crease in my real chest. I ran back to the bathroom to check myself out.

When I looked in the mirror I was amazed to see how sexy my already girly body had become. It was a euphoric feeling of sorts, looking at my head on this beautifully feminine body and knowing that it was my own. Looking at myself from head to toe I examined each part of my outfit. My top was a light pink crop top that matched the 3 piece lingerie set I was wearing underneath. It had a deep v neck that highlighted my clavicles and cleavage, and had mesh long sleeves with floral lace decals going down my arms. The crop top left about two inches of skin showing before the top of my skirt, that fit perfectly on the skinniest part of my tummy. The skirt was a black high-waist flared A-line mini skater skirt that really accentuated my hourglass figure. The shape was frilly enough to keep my clitty unnoticeable, but tight enough to hug my lower back before flowing over my plump booty. At slightly above mid thigh the skirt ended and my lacy fishnet stockings started. The fishnet gaps were very close together and had a floral design sprinkled throughout which completely hid my leg hair, but still showed off my tan. My legs looked amazing in them, and although my muscles were subtly defined they still looked soft and supple. The tights continued down past my calves and onto my feet strapped in their 4” black ankle strap stilettos with an open toe letting my pink toenails peak through the fishnets.

Wow. I looked incredible. With my pink fingernails I lifted up my skirt to see my little thong had my swelling clitty and bronze ass hiding beneath, and in that moment I felt so sexy. It was going to be hard not want to look underneath my skirt all night, but I guess that's what makes skirts so irresistibly appealing. I was so horny, but I again tried not to think about it and shifted my focus to putting on the finishing touches. After some struggle getting used to my long nails I put on the jewelry I ordered. A few bracelets, a choker necklace, clip on earrings, and a bunch of rings I had ordered. Then, finally, I put on my 18" curly dark-root blonde wig which sent me into a multiple hour session of posing, modeling, and mirror selfies. All that time forced my clitty to recede to an acorn size resting state with some precum I tried to wipe from my thong as best as I could.

I eventually look at the time “shit!” I yelp frantically as it’s definitely time to go. I hastily grab the butt plug and apply a little lube to it. I wish I saved more time for this instead of taking so many selfies posing in the mirror. I rest my forearm on the vanity, put my heeled foot on the toilet and force it in as quickly as I can after about 5 minutes of focus and mild pain. I’ve got to go though and I race to grab my pink faux suede clutch and put my phone, ID, and credit card in it. I take one last look at the sexy girl in the mirror before I call the uber. Am I really about to do this?

After an awkward uber drive of dodging suspicious stares from my driver in the rear view, I finally get to Amy’s at 7pm. I’m feeling nervous as I approach the door, but there really isn’t anywhere to hide outside the apartment either. I’m outside of my comfort zone either way. I gather myself, stand tall in my heels, take a deep breath, and knock on the door.

“Um hello?” A man greets me with as he opens the door.

“Uhh hi. I’m Sam, Gabby’s boyfriend.” I clamor, obviously nervous.

“Oh uh sure, come on in. I’m Amy’s husband Greg”. He responds while motioning me in, clearly taken back by my costume.

“Sam?” Gabby’s voice echos like a knife through the air.

I turn to see her in the kitchen, standing next to Amy. Both with mouths wide open as they take in my outfit.

“Just need some makeup and I should be sure to win the costume contest.” I say as I gesture my arms to the side and curtsy. A pose I’ve been practicing. I didn’t know if there’d be a costume contest, but the awkwardness forced me to do some quick thinking on my feet. Alluding to my over the top feminine outfit as a competitive thing felt like a nice masculine approach.

“Wow you look sexy!” Amy exclaimed adding some excitement to the air.

“Yeah, wow Sam… You really look like a girl.” Gabby added less enthusiastically, but felt like a compliment nonetheless.

“Thanks boys.” I say as I cat walk over to Gabby and grab her flannel collar giving an overdone wink and a kiss on the cheek. She gives me a quick smirk as if she is realizing this is a Halloween character and I feel relief flow over my body.

“How about some wine miss?” Amy asks, clearly enjoying the role playing.

“Please mister.” I respond.

“Big pour for me.” Gabby adds.

Some time passes as Gabby takes in my outfit, and Amy drills me with questions. Her husband gone and clearly avoiding us. I keep glancing at Gabby as I make small talk with Amy, trying to get a read on her face.

“Well I’d love it if I could do your makeup!” Amy eventually circles back to. “Is that alright Gabby?”

“Sure, I think James, Sarah, and Mark are getting here soon, so I’ll let them in.” Gabby replies as she sits down, making it apparent she isn’t coming with.

Amy and I retreat to her bedroom where her husband comes out of the bathroom wearing a big red dress with basketball shorts, high socks, and a cheap Halloween store wig that makes him look more like a rockstar than a girl.

“I’m going to do Sam’s makeup honey, do you want me to do you next?” Amy asks her husband.

“Uh no thanks.” He responds quickly getting out of the same room as me.

“Buzzkill.” Amy says as she motions to me to sit in the chair. She spins me around and begins applying makeup as I face her. I wasn’t sure what was happening, but I felt a mixture of liquids and powders all over my face. She then focused on my eyes, and asked “Would you like some fake eye lashes?” Gabby asks. “Whatever it takes to win the costume contests at the bars.” I respond. She then focuses on my lips.

“Wellah!” She says in an Italian accent as she spins me around to see myself in the mirror.

Wow.

There I was, a completed woman. My smoothly foundationed face looking back at me with some light pink Smokey eye shadow matching my nails. Red lipstick surrounded my open mouth. A tear starts to roll down my left eye after pooling on my big black eye lashes.

“Rule number one of being a girl, you can’t cry when someone just spent a half hour on your makeup.” Amy says breaking my trance, and handing me a tissue.

“Thank you so much.” I say as I continue to stare into my own reflection.

“Of course girl, let’s party!” Amy says clearly ready to show off her work.

The rest of the pregame was a little awkward. Most the men avoided me after the initial introductions of Gabby introducing me to her coworkers dressed in comparable costumes to Amy’s husband. The girls, however, seemed to have a lot more fun with my outfit. Holding my hand to inspect my pink acrylic nails, eyeing me up and down, and asking how in the world I got convinced to do this. The more attention I got from the girls, the more I resorted to my feminine mannerisms I had been practicing. As the night went on, however, I noticed Gabby slowly becoming more avoidant with me. Nonetheless, after a few bottles of wine and some group photos it was finally time to go to the bar.

The first place we went to was a club with a decent line out front. It was Amy’s idea since it said online they had a costume contest at midnight. As we stood there in line I thought to myself there’s no way I will make it until midnight. I probably had a bottle and a half of wine at the pregame, and I forgot to eat dinner. Safe to say, I wasn’t feeling as confident balancing in my heels as I did at home. However, seeing my reflection in the tinted glass was giving me all the confidence in the world in my outfit.

“Gabby?” I heard a man ask as I turned to see what I can only describe as a classic tall, dark, and handsome man around our age dressed as a half ass pirate.

“Jameis!” Gabby said as she lunged into him for a hug. He was standing a full 4 inches above me, even in my 4” heels. “What are you doing here?”

“Amy texted me that you guys were heading here and I figured I needed to buy you a drink after the long hours you’ve been putting in at work.” Jameis said right before turning his eyes to me. “And who is this lovely lady?”

“This is Sam.” Gabby said without elaborating. Then Jameis reached out and grabbed my dainty jeweled hand and brought it up to his mouth to kiss it.

“Well aren’t you beautiful.” He says calmly, staring directly into my eyes for a second before I nervously smile and look away.

“What the fuck Sam?” Gabby breaks the air angrily.

“Wha-what?” I respond embarrassed and confused.

“Jameis, this is my boyfriend Sam. He got a little too into character for Halloween tonight.” She said, clearly irritated with me.

“Wow well you could’ve fooled me.” Jameis said laughing, making the situation lighter.

We entered the bar and Gabby ditched me as fast as she could. I saw her taking shots at the bar with her coworkers as if she was on a mission. I was feeling all kinds of emotions. Quite honestly I wanted to cry. “What the fuck was that?” I thought thinking back on how Gabby’s clearly watched me melt from her coworker’s flirting. I eventually found an open seat at the bar, and sat in it as I tried to gather myself.

House music blaring, people dancing all around, and here I am feeling stupid as I sit with my nylon clad legs crossed in a bar stool to keep my pink thong from showing under my black skirt that I noticed rose above my thigh highs as I sat. My flat tummy changing colors with the DJ lights as I look down past my artificial cleavage. “This was way too much. I completely overdid this and now my girlfriend and all her coworkers are going to think I’m gay.” I thought as I brushed my blonde wig over my face to hid the fact my eyes were watering up.

“Pretty girl like you alone at the bar and nobody has bought you a drink yet?” Jameis’s masculine voice pulls me out of my self wallowing.

“I uh, I was just about to go.” I wipe my eyes flustered.

“I know you didn’t put that much effort into looking so beautiful, just to go home at 10.” Jameis says as he motions to the bartender the number 4.

The playboy bunny bartender comes over and goes, “what’ll it be?”

“Two shots of tequila, an IPA, and a cosmo for the pretty lady.” He responded in a polite but controlling tone.

To my surprise Jameis was actually pretty cool. He chatted my ear off and kept asking me questions about life. He didn’t focus on the fact I was dressed like a Barbie, and instead asked about me. Where I went to college, what I studied, how I like Seattle. I found myself enjoying just talking to him as a friend. Another round of tequila and a cosmo later, and I could definitely feel my words starting to slur. I naturally began laughing more and even playfully slapping Jeremy’s chest when he said something funny. He was a grade A charmer, even hitting on girls coming and going around us with one liners that made them giggle before disappearing into the crowd.

“Well I suppose you should probably go find Gabby.” Jameis snaps me back into the reality of my situation. “I see her on the dance floor, I’ll help you get over there.” He says engulfing my hand within his and walking slowly as I cat walk with him onto the dance floor.

Gabby sees this and instantly pushes through the crowd to Jameis. She wraps both her hands around his neck and says something as Jameis lets go of my hand. Gabby starts dancing seductively with a big smile on her face as she holds Jameis’s hand above her head swinging her hips back and forth a few inches from his groin. Jameis plays it cool and smiles as he twirls her and then reaches his hand back out to mine noticing my awkwardness. He begins to twirl me, and I follow Gabby’s lead and begin to sway my hips. I know I’m not the best at dancing, but I closed my eyes and just pictured how I might look now with my dance moves I’ve practiced in the mirror at home this month, and safe to say I was feeling myself. Jameis started pulling Gabby and I together to dance with each other. Gabby jokingly started grinding on my butt, and I saw it as an opportunity to finally flirt with my girlfriend tonight. I started moving my plump butt in a circled against her groin.

After a few seconds though I felt her presence on my backside drifting and I peaked over my shoulder to see her grinding her ass into Jameis’s crotch as she held my hips. This made me feel weird and I noticed the glances of the people we came with as I started to stand still in my drunken haze with my girlfriend behind me grinding on another man. Jameis seemed to have picked up on this, and in a respectful manner guided Gabby’s ass off of him and in fromt of me onto my groin. Without missing a beat Gabby continued her promiscuous grinding on me, and I started to relax and get into the rythym again.

As I danced to the beat I felt Jameis’s hands move to my hips. As if his goal wasn’t to get me to take his position on Gabby, but for me to take her position on him. I just went with the flow to not cause a fuss. After all my beautiful lumberjack girlfriend was grinding her ass on my now hard clitty and I was focusing on that feeling. Until I felt it. Jameis had now pulled himself in closer and was slowly pressing what could only be his bulging dick slowly between my plump, skirted ass cheeks. I looked around frantically, but to my surprise nobody was really staring. I guess we just looked like two girls and a guy having fun on the dance floor.

I relaxed back into my drunken haze and let Jameis move my hips in unison with his as I did the same to Gabby. He continued to slowly introduce more pressure until I could feel his dick pressed against the cap of my butt plug. As I rotated my ass in a circle to the music the sensation of the plug circling within me started to capture my attention. I started to push back into him to chase this feeling, as we grinded harder and harder into each other.

*SMACK*

I came back to reality to an abrupt slap from Gabby.

“What the fuck Sam you faggot!” she screamed while tears flowed down her face.

I looked around to a circle of people staring. In a shear state of panic, I starting crying and ran out of the bar as fast as I could.

I ubered home alone, went up to bed and began undressing. Cursing to myself, “way to go Sam now the only people you’ve met here think you’re gay.” I took off my pink crop top, black skirt, and god forsaken butt plug so I was just standing in my heels, stockings, wig, and matching pink lingerie set holding my shrunken dick and fake boobs, completely disgusted with myself.

However, then I caught a glimpse of myself in the full length mirror to see this sexy girl in lingerie staring back at me with her smokey eyes. Still drunk, I thought, “I didn’t get any pictures in lingerie yet. I might as well since this is the last time I’m going to wear this stuff.” I reassured myself, fully intent on throwing everything away. I grabbed my phone and struck a few primiscuous poses. My clitty started to harden as I repeated this process of feminine poses, snapping photos on the bed, and reviewing my burlesque photography. I started to get really horny and began rubbing myself through the front of my thong with my pink fingernails. Until I heard the front door open.

“Hello?” I heard Jameis’s deep voice call out from downstairs.

I quickly jumped under the covers and played possum. I heard him heavily walking around downstairs. Then I heard his footsteps start to come upstairs.

“Hey” he softly whispered as he rocked my shoulder back and forth. I rolled over and batted my eyelashes acting like I had just woke up. “Gabby blacked out, I brought her home and put her on the couch. Are you ok?”

“Uh yeah I’m fine.” I muttered back.

“Really? You’re still in your shoes.” He said as he motioned to my heels sticking out from the bottom of the covers.

“Oh uh yeah, I guess I am.” I said nervously.

“Here let me help you.” he said as he sat down at the foot of the bed and started unstrapping my heels from my ankles.

“I bet your feet hurt from wearing these all night.” he said as he starting to rub them.

“I’ve sort of built a tolerance.” I replied, letting onto more than I should.

“Oh you wear heels a lot?” he question as he continued massaging.

“Um no, just to practice for tonight.” I replied.

“What were you so excited about tonight that made you practice for it?” he quizzed back as he switched to rubbing my other pink toed foot.

“I guess I was just excited to embrace my feminine side for once.” I said honestly. “But after tonight I’m probably hanging up my heels.”

“Well I’m glad you did, I hope its not the last time.” Jameis said as he slowly rubbed his right hand over my nylon covered shins.

I let him, still horny from rubbing myself before. It felt good being pampered. His left hand stayed squeezing my foot, but his right hand slowly drifted above my knee and up my thigh. I shivered a little bit as his fingertips brushed my skin just above my stockings and sent chills down my spin.

I now realized I wanted to feel more of this. I reached my left hand down to my thigh to meet his and gave it an endearing squeeze.

He took my invitation and climbed under the covers and started kissing my legs. From my shins to my thighs sending shivers down my spine every time. He paused for a moment at the top of my thighs as he realized I was only wearing my 3 piece lingerie set under the covers. He began kissing again, first my hip then a little peck on my raging clitty letting me know he knew i was liking this. He continued up to my stomach, then my breasts, and eventually we were staring eye to eye with him stradling me, his knee pressing between my legs.

I just laid there in a trance. Horny as can be. blinking my long eye lashes as I stared at him thinking “Your move.”

He took his big hand and brushed my hair behind my ear and whispered “I’ve been waiting to do this all night.” As he leaned in to kiss me. I met his lips with a gentle peck of my own. He backed off and looked at me again, but I wanted more. I wrapped both my arms around his head and brought him to my open mouth. We starting sucking lips, and tasting tongues. As I focused on my first kiss with a man, his hand drifted down the side of my body down to my ass to squeeze as we made out. I instinctively brought my right leg up to give him a rounder cheek to squeeze, and he reacted by driving his knee further between my legs. As we laid there making out, I started to gyrate my hips in a circle as if trying to work his knee deeper between my butt crack like I did when we were dancing. Not for long though, as he cut short my grind by retracting his knee and breaking our kiss. As he did he slowly moved down the bed.

“Do you really want to feel like a girl?” He whispered.

“Mhm.” I shook my head in reply, not sure what he meant, but knowing that in my heart thats all I wanted from today.

“Then roll over.” he said. His voice strong and commanding.

I submitted, and rolled onto my belly.

“On all fours please.” he directed and I listened. Having never been in a position like this I was feeling vulnerable. Here I am in my pink bra, garter, and thong. On my hands and knees. With a blonde wig, fake tits, jewelry, full makeup, and thigh high stockings. with a man behind me and my girlfriend sleeping downstairs.

As I waited there for my next command Jameis began massaging my ass as I felt him positioning himself behind me. He hooked a finger around my thong, and pulled it to the side of my ass where my right cheek was plump enough to hold it in place. I then felt his wet fingers begin to rub up and down my crack and around my hole.

As I shuttured he gently wrapped his hands around my hips and leaned forward until his dark mushroom was pressing against my tight little hole. This was happening faster than I had expected, but then he just stopped, and I froze wondering why. Did I do something wrong? But then I felt a warm stream of saliva pooling right where the head of his cock touched my gate. And just like that I could feel my body melt and myself open up like it did with my butt plug two fays before. As my flower bloomed bigger I felt myself melting back into him to fill the ever increasing hole.

But then I stopped, I had to. It was just too big compared to my butt plug. Feeling my change in tension, Jameis lightly grabbed each of my plump little buttchecks with his entire hands, and says “with an ass like this you’d make any girl jealous.” Motivated I move both my hands straight forward and clasped the bed sheets to push myself back onto his tan cock.

It hurt, but i just took it slow and got about half of him inside of me before backing off completely. Thats when I got the first glimpse of a new sensation. Curious, I lined myself up and pushed back into him. I felt him drop another pool of drool as I did and with the extra slipperiness I just went for it and pushed back hard until my ass met his pelvis.

Pain. Again I evacuate entirely from him, but even faster this time. There it was again. At that moment I realized that it was actually the way out that created that new sensation. Again he reads me and says “just take it slow sexy.” I could tell he was holding as still as possible allowing me to explore him at my own pace, but little did he know my mind just went from nervous and confused, to knowing exactly what I am chasing. I react to his encouragement by pushing my now looser hole back into his sopping wet meat. And then slowly off, but this time stopping just before the head of his cock so that he remained inside of me.

“mmm” I lightly moan, almost instinctually. I push back again slowly filling myself until my ass hits his pelvis once again. I slowly pull my ass forward and let out another soft moan as his dark helmet drags across my prostate.

I’ve got it down now. I push back and repeat this motion over and over while I chase the feeling of his throbbing member rubbing across my prostate. As I begin to get a rhythm down he pushes down on my shoulders and I follow his lead until my face is pressed against the mattress. “Good girl” he says, “now let me take it from here.”

With my back fully arched under his weight it was hard to rock back and forth, so I just stopped, relaxed, and focused on the feeling inside of me.

Jameis began fucking me slowly. Matching the pace I had set. I was free to focus completely on his cock as he entered me over and over. I was having sex tonight, as the girl I trained all month to be.

As I focused I began to realize that if I flexed my anus tight as he was inside of me the feelings amplified. I kept flexed, but immediately regretted it when he entered me again. That was the trick.

When he pushed his cock into me I began to relax and I could feel myself loosen as I accepted him driving into me easier. However, as he pulled out I began to flex tight around his cock, squeezing it, as if to say please don’t go.

Fuck that felt good.

As Jameis did all the work thrusting in and out of me, I repeated my new exercise. Relaxing myself as he entered me, and gripping onto him as he tried to leave.

“Fuck I love when you moan!” he said pulling me out of my trance and back into the room. Apparently I was liking getting dicked down and I was liking it out loud.

“Don’t stop.” I managed to whisper back.

He reacted by picking up his speed and I reacted back by re-digging my pink nails into the sheets to steady myself as he began pounding into me harder. I felt my mind leave my body. Looking down at myself in a euphoric trance, eyes closed, back arched, face buried, dressed in sexy lingerie as this man pleasured himself with my ass that I’ve tanned, shaved smooth, and worked out for weeks. I think deep down I did it all for this. I spent hours perfecting myself to be a girl, but a girl that i knew would be desirable to men.

Then it happened. As I came to terms with my undeniable passage into womanhood. I felt a wave move from my ass at the epicenter, out to my head and my pink curled toes. Then an intense tremor followed as I felt myself start to shake uncontrolably.

“Ooooh fuuuckk!” I shuttered, as my erect penis that I’ve been compltely neglecting started squirting more cum than ever before into the front of my floral lace thong. He kept hitting my special button and I kept orgasming as I moaned and squirmed uncontrollably beneath him.

“Fuck you’re going to make me cum.” Jameis said panting. At the same time I felt him press himself as deep inside of me as he could. Unable to support his body weight I fell to my belly and felt my warm pool of cum surrounding my clitty. I then felt a new feeling of a light spurting repeating deep in my boipussy as my first man slowly filled me with his warm seed.

I embraced him once more by squeezing his meat with my weakened ass muscles one last time, as if to say thank you for visiting. Still softly moaning like a girl coming down from an orgasm.

He collapsed on top of me. For a few moments we just laid there. My face and body pressed between the bedding beneath me and my hunk behind me. Pressed into the bed by his full body weight, well aware that I was here for as long as he wanted me to be. I hope long.

“How about one more squeeze for the road.” Jameis whispers into my ear as his breathe sends shivers down my already vibrating spine. I use those chills to muster up one more kegel around his softening rod, wringing out the last bit of cum into my already full guts.