New Friends and a Roommate Ch. 03

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Breaking Up Is Hard To Do.
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Part 3 of the 3 part series

Updated 06/10/2023
Created 02/14/2021
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I had a lot of firsts the last two days but tonight was nerve racking and wrong in the finest sense of the word.

The girls feminized me through my desire to be feminized, at least that's what the proof boils down to, but that's just the beginning. After transitioning me into an absolutely beautiful female they set me up with my roommate that has no clue to who I am, except that my name is Bridget.

Our date consisted of pizza and then making out at the movie theater, yes, I made out with my roommate; but it wasn't my first choice. My first choice would be to preferably go home and hide my head under a pillow but I didn't have an 'actual' choice. I mean, it was either Todd or social media.

Todd had no idea who I was as we sat next to each other and talked. First we discussed the movie and then he turned the subject to me which really spiked my nerves; still I completely passed as a female. In fact, I passed so well that he kissed me... my very first kiss... ever. That's right, I've never been kissed by a girl let alone a man, but here I was, on a date with my roommate; my defenses annihilated.

The first kiss shocked me, the second kiss was a bit confusing, and the third one had me. I have to admit that his kisses seemed so natural that I wanted it to never end.

However, as we continued to kiss, his hand had made its way between my legs close to my secret, and my hand 'somehow' was stroking his cock. Now, anxiety began to build, and it was time for an immediate exit before I was found out.

Once outside I knew I would have to either satisfy him orally and/or let him fuck me. If neither happened the girls probably would release the video and I couldn't let that happen so I choose the blow job just because it would postpone the serious ass beating I would receive if Todd figured out my true identity.

Now, I'm at the bar, and Todd is waiting for my choice of drink.

"Todd, you're forewarned, I'm on my period, so if anything happens it will have to be oral or anal," I whispered in his ear.

"My kind of girl," he whispered back as we both laughed.

"I'll let you choose, not too harsh though," I commented.

"Are we talking about drinks or sex?" he whispered back.

"The drinks," I smiled as I just realized what I had done. I offered him anal sex, to pull my panties down, and possibly discover my secret. I asked myself why I didn't just offer him a blow job; it's would be safer, easier, and much more convenient. With that in mind, maybe I want it to happen.

"Two Blue Moons bartender."

I knew I was in trouble as soon as the rim of the bottle touched my painted lips. After everyone finished round one everyone opted for another but I declined. It was a long night and we had plenty of time for seconds if I felt I could handle it.

Todd led me out to the dance floor and again my nerves hit as I had no idea what to do. Then the DJ played 'Girls, Girls, Girls' a Motley Crue song. Any kid that had a mom and/or dad that was in this style of music definitely knew this song. Their hard driven music was easy to move to so that's exactly what I did, moved to the music. I was totally into it after the first minute I began moving like a free spirited girl in a music video with my hands in the air and my hips swaying. For the first time I felt free, no worries, no hang ups, just a really good time.

"You're a great dancer," Todd told me.

"Thanks, you're not too bad yourself."

Lady Gaga followed, then Blondie, Britney, Justin, Kanye, and the list went on. Then the dreaded moment, a slow song, he placed both hands on my lower back, pulled me close, and kissed me. He not only grabbed my ass but his cock hardened between our bodies letting me know he was definitely excited.

More dancing, more kissing, more touching, and more beer became the night's routine.

"Want to go to my place?" he whispered interrupting my trance.

"Are you driving?" I giggled as I pulled my hand from the front of his pants.

"I'll call Uber."

"Just as long as you're driving, I'll go," I answered.

Once we were back at his place.

"This looks so familiar," I giggled.

"Just your typical condo on campus," he replied as he shut the other bedroom door.

"Do you have a restroom?"

"Sure, it's in my bedroom to the right."

"Thanks," I said as I made my way to the restroom to relieve myself. Then, I remembered, I didn't have a v-jay, I had a penis. Have you ever had one of those 'get sober' moments? I never did but I just had my first and it was a kicker, though I must admit, I was still wasted to an extreme point and decided to sit and relieve myself and the tidied up.

I was determined to finish what I started or face repercussions from the girls.

"I thought you got lost," he joked.

"Almost, I swam to shore," I giggled as he kissed me.

Again, his kiss sent me to a faraway place as only this moment existed.

"Beer, juice, water? He asked.

"Water please," I was parched and needed a relief.

"Music?"

"Sure, why not?"

"I have something you might like."

I laughed.

"What?" he laughed," you don't like Barry White?"

"How old do you think I am?" I laughed.

"Okay, you name the tune."

"How about... Lady Gaga, Justin, Motley, Accept?" I laughed.

"I don't know who Accept is?"

"Play Hollywood Undead, I saw them about a month ago in LA."

"Interesting, I don't remember seeing you there."

"Why would you?"

"A beautiful girl like you would be hard to miss!"

"Thanks... Hollywood Undead?"

"Fine, Hollywood Undead it is. Google... play," he finished as I began to sway to

'Everywhere I Go.'

He moved in close, wrapped his arms around me, and kissed me. I wasted no time and reciprocated letting his tongue enter my mouth... this is what I wanted... this is where I wanted to be, and this is who I wanted it to be with.

I moved my hips against his body as he became hard as a rock. The music, the kiss, in his arms, and the thought of his cock in my mouth put me into a dizzying spiral of drunkenness.

I reached between us and unbuckled his belt, unbuttoned his shorts, pulled down his zipper, and immediately grabbed his cock and began stroking him like I was a porno star.

He quickly stepped lowered his underwear and stepped out of his clothing while I peered down looking at his impressive manhood.

Honestly, I felt like a woman, or what I thought a woman would feel like in his arms.

He picked me up by the bottom of my ass and carried me to the bedroom and heard another Hollywood Undead song start to play.

He laid me back onto the bed as our lips stayed lock in a forever kiss.

Somehow, throughout the night, I fell for Todd. He was handsome, witty, and a genuine nice guy.

Somewhere during the kiss I found myself between his legs with his cock in my mouth. He was completely nude by this time and I still had my clothes on.

"Mmm," my lips felt every vein in his cock as I bobbed up and down.

"'Oh yeah."

"Mmm," I couldn't remember a better time than right now except for that first kiss in the theatre.

"Oh my gawd," he moaned.

"Mmm," his moans were music to my ears as I knew he appreciated my mouth as much as I appreciated him letting me please him.

I had no idea how long I was in this position but I was relaxed and enjoying it.

He laid a hand on the back of my head as I bobbed but gave me the freedom to move at will which I thoroughly appreciated.

"Ah gawd, I'm cumming," he muttered trying to forewarn me before unloading rope after rope into my wanting mouth.

"Mmm," I definitely enjoyed swallowing his load and sucked until he was empty.

Then we lay there until he spoke.

"Sorry, I tried to warn you," he apologized.

"No problem, I enjoyed it," I pecked him on the lips then laid down beside him.

He kissed me as I played with his cock until it hardened in my hand; which wasn't long. Then he motioned me to turn on my stomach, I knew what he wanted, and willingly obeyed.

I got on all fours and then kneeled as he reached for the nightstand. While his attention was elsewhere, I rearranged my pad that I applied in the restroom, and tucked my junk forward; after all, I was on my period. This was supposed to protect me if I were to find myself in this position; a tactic for self-preservation. The girls trained me well.

Lisa had given me panties that not only could hold my junk in place but also had an anal opening for easy access; she must be one kinky bitch.

"Ah," I moaned as he inserted a slick finger into my ass.

"Are you okay?"

"Yes, I'm fine," I answered as he took his time finger fucking me. I appreciated him taking his time with each finger as I was now pushing back on his third finger wanting more of him inside of me.

He mounted me from behind, grabbed my hips, and slowly pushed his huge head into me.

"Ah, ah," I cried out as I lowered my head; his cock is bigger by comparison then the others, I had the video tape.

"Are you okay?"

"Yes, just fuck me," I panted.

He took his time until my canal accepted his erect cock.

"Ah," I panted as I was glad he was finally deep inside of me.

He waited until I was stretched and then began to slowly fuck me.

"Yes, mmm," I moaned every time he entered me.

Todd slowly increased the speed of his thrusts until the sound of his balls echoed throughout the room as they slapped me in my ass.

"Ah, ah, ah," I hysterically panted as he pounded me.

"Fuck," he moaned as he continued to fuck me.

"Ah, ah, ah," I found myself pulling forward and slamming back against each and every thrust as I became obsessed.

"Fuck," he continued to moan.

"Fuck yes," I moaned.

"Ah, ah, ah," he panted.

"Oh gawd," I screamed as I came in my panties.

He continued to hammer me for another hard fifteen minutes before he unloaded shot after shot into me which made me cum again.

He collapsed beside me as we both panted in the afterglow.

I felt so satisfied after a night of sexual tension.

"What time is it?" I asked.

"Two am."

"I got to get to Lisa's house," I said as I sat up.

"You might as well stay here; my roommate hasn't come home yet so he probably got lucky himself," he offered.

I began to laugh.

"What's so funny?"

"Nothing, I'll stay under one condition."

"Anything."

We agreed no more sex until further notice and fell asleep in each other's arms rather quickly.

In the morning I was the first one up and realized it wasn't a dream but I actually fucked Todd last night in our condo. I rushed to the restroom, relieved myself, and tucked properly. When I came out Todd was still nude and sleeping.

I grabbed my purse and locked the door as I left. I walked the few blocks and rang Lisa's door bell.

"Hey, Bridget, come in," Lisa invited me in.

"Hey Lisa."

"You two disappeared early last night."

"I think we left around mid-night."

"That sounds about right."

"Can I get my clothes please?"

"Sure, follow me."

Once upstairs she asked me to undress because she had a few gifts for me.

"What kind of gifts?"

"Just get undressed," she told me; her demeanor changed a lot from last night... she was extremely nice to me.

I did.

"Bitch, you got lucky last night," she smiled as she pointed out the wet spots on my panties that were still there because they couldn't air out; late night, early morning.

"You fucked him didn't you?" she asked ecstatically.

"Yes," I admitted feeling accomplishment.

"I knew you two would hit it off as soon as he saw you."

"How did you know?"

"He walked right into a wall last night," she laughed.

"That was rather interesting."

"Here, I want you to have these," she said laying out ten dress, six tops, three t-shirts, skirts, and shoes with a few pieces of jewelry.

"Don't you need this stuff?"

"Mom's taking me shopping, that means a whole new wardrobe, so feel free to take them," she told me.

"Thanks."

"Oh, here, take some jeans," she told me as she tossed them to the bed with some more clothes and shoes.

"I guess I can't keep this stuff here," I began.

"Sorry, but I'll have so many new clothes I just won't have the room."

"But Todd will see this stuff."

"You're going to have to come out to him anyway sooner or later."

I sighed.

"Here, we'll pack everything in this suitcase and I'll drive you home. Whenever you dress up you'll have everything you need at your fingertips."

"Thanks," was all I could say at the moment as I needed the clothes when called upon.

"We're all going out tonight to a huge party so I expect you to be here by 3pm dressed in this dress," she said holding it up.

"I need boobs to wear that!" I exclaimed.

"I'll send you a link how to fix that and here is a roll of duct tape."

"Duct tape?"

"Just watch the video and be here by three," she said as she began packing everything in the suitcase.

"Todd's got to be somewhere in an hour so can you drop me and my new clothes off at the condo so I can prepare and get back over here before Todd gets back?"

"No problem."

Lisa dropped me off at my condo but once inside it felt different... I felt different.

I just fucked my roommate and understood our relationship would never be the same. In fact, how could I possibly explain what happened last night?

The small kitchen table seemed different and so did the kitchen as I looked through it and out the window on the other side of it.

It wasn't a hard decision to make... I was going to leave. I would leave before three and before Todd would be expected back. I couldn't worry about social media or anything else right now; I just needed to escape and work this out for myself, for that, I needed to go back home, back home to Iowa and not the California vacation house a few blocks away, If I was going to do this I need to actually get away, far away.

I felt something at Lisa's apartment when I went in; I felt it would be someone else's turn to have their way with me, the rotation, that wasn't going to happen... not this time.

I pulled the pink USB memory stick from my pocket and put it next to my computer and began writing Todd a letter.

***

"Dear Todd."

"The night we went to your friend's house turned out to be a nightmare as you can see from the video. I never thought of being a female let alone being feminized in any way, shape, or form. However the video shows a different side of me that I never knew existed."

"I thoroughly enjoyed my feminization to a degree of happiness. Whether it was acceptance or just plain stupidity I will have to work that out on my own, at home, amongst family."

"The only good thing that came out of this was our time together but unfortunately

I'm not the person that you think I am."

"I'm so sorry!"

"Love you, always,

"Bridget."

***

I sealed my letter in an envelope and wrote a message on the outside, "Please watch the entire video and you will understand what happened."

I pulled a new outfit out of the suitcase including makeup. I tucked, applied a little makeup, dressed in a nice tight sexy dress, and booties. I packed everything Lisa gave me and left my boy clothes in the closet.

I placed the pink USB, the letter, and a watch on Todd's lap top before I left.

Once at the curb I signaled down a taxi and asked him to take me to the airport. There, I would figure out a way to get home... even if I had to change plans and take a bus.

Luckily, there were a few empty seats on the flight to Iowa. I gave my passport for proof of identity to the counter person. She began to question the document but had second thoughts when I wiped away a tear making its way down my cheek.

"Have a good flight," she said respectively as she handed the paperwork back to me.

"Thank you," I sniffled as I went to my terminal.

I boarded in the same fashion, wiping away tears, and found my seat.

Nothing could change the reality that I was in love with him. The games, concerts, and every minute with him was a lifetime experience... if I had only been born a female.

I cried as they lifted off the runway.

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