Exploring My Life as a Woman Pt. 04

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Continuing my transition, a sexual feast and a heartbreak.
11.2k words
4.75
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Part 4 of the 5 part series

Updated 06/10/2023
Created 10/21/2020
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Afterhours22
Afterhours22
1,129 Followers

Almost four months have gone by for our girl, Dawn. Changes, both physically and emotionally have occurred for her since the start of HRT (hormone replacement therapy). She has also, on her doctor's referral, started seeing a therapist who specializes in helping transgender women.

Dawn underwent a minor procedure to enhance her lips just and the result was stellar. Baby steps on the road to transitioning, she calls it. Miranda swore up and down that she now looked just like a shorter version of the actress that played Jessica Jones, with her long black hair and now with lips to match.

Christmas was quickly approaching, and the snow has begun to fall in the city.

I used to hate shopping, especially for myself. I never knew what outfits would look good on me or not, but now things were so much different. My body was changing, filling out in all the right places. My jeans fit even better than before as my hips started to get a little wider. I kept to a good healthy diet and have started a strict walking regimen along with resistance and weight training to help my body build muscle and tone.

My tummy was getting flatter and my waistline dropped an inch or more to give me a nice jump start to look even sexier than before. Oh, and my breasts were starting to form! Small mounds were growing behind those ever extremely sensitive puffy nipples of mine. I was wearing a padded A cup bra now that gave me the confidence to wear tops that were a little more conforming.

As I finished getting dressed in front of the mirror, I turned my body around both ways to see if I looked okay and all was in order. I smiled at myself, then went out to the hallway to put on my winter boots, coat, earmuffs, and gloves. Grabbed my bag and headed out the door to meet up with Miranda and Carly to go SHOPPING!

Carly had become a new part of our little group over the past month or so, since her bad break up with Dan, which nearly drove her to self-destruction. Miranda and I, of course welcomed her in with open arms and spent many hours by her side to help with her broken heart. Now we are all stuck together like super glue and rarely did anything apart.

We hit several of the local clothing boutiques around the business district, bought a few things and enjoyed the walk in between. It was lightly snowing and with the Christmas decorations around the city, it made the evening beautiful.

We finished our last shop and stopped at one of the coffee houses in the area for some hot mochas to take off the chill. We sat there chatting about the upcoming holidays and what plans we had to make, gifts we needed to buy yet and then as usual, our conversations always turned to sex. That was just us.

Carly asked, "Dawn, how are things going between you and Brad these days? It seems like the three of us have been spending a lot of times together and you haven't mentioned him."

I sat quiet for a few moments then replied, "Well, we were spending a lot of time together there for a bit in the beginning, but we decided to cool things down some because neither of us wants in a committed relationship. We want to remain friends and get together occasionally but, Brad still has other people he sees and did not want those friendships to come to an end."

"Dawnie, you know that is a load of crap," piped Miranda, "You really like him and did not want things to cool off so just stop with that nonsense."

"Well, that is true to a point," I replied. "I did not want to lose him either by setting any boundaries in our friendship. That way, we can get together occasionally and still fuck without hang ups," I said a little too loudly, garnering dirty looks from some of the prudes sitting around us. The three of us giggled, finished up our drinks, hugged and kissed goodbye outside, then headed home.

I just got in the door and my phone rang. Speak of the Devil himself. I answered, "Hi Brad, how are you?"

"Hey Dawn, I'm good and thank you for asking," he replied, "How have you been doing?"

"Never better," I said in my best Hermione imitation. Yes, I love the Harry Potter series, so what? Brad chuckled on the other end of the line.

We got through the hi, how are you typical greetings then he asked me if I was free the next evening for dinner and a movie. The local discount theater was showing some old classics that we both loved, and I readily accepted his invitation.

"I'll pick you up at 5pm unless that is too early," he asked.

I told him it would be perfect, and I would see him then. As soon as I hung up, I texted Miranda and Carly to tell them I had a date. They texted back smiley faces, thumbs up and poop emojis just because they liked to be silly bitches.

Brad picked me up on time, as usual. He is the punctual one. We went to an old steel trolley style diner across down, which I absolutely adored, and had some very tasty veggie burgers. They had the little miniature juke boxes at each table that we listened to some music through and just caught up on our busy lives. We finished up and headed to the theater.

The old Movie House, it was called, and it had seen its better days, with its 80's era seating and outdated sounds system, however, watching a classic older movie there was perfect. Brad got some popcorn and water for us and we headed in to get a seat. There were just a small number of other people inside, so we went to the back corner away from them so we could quietly chat and not disturb anyone.

The movie began and we settled in snacking on the popcorn and idly whisper chatting at scenes we knew. Something about old classic romantic comedies though made me horny. Of course, these days, it did not take much to make me horny. I do have to say that I am triggered by different things now than before I started my HRT.

Romance, cute smiles, pretty eyes and sweet talk were the keys to start my motor now, including listening to Brad whisper to me. I looked at him and grinned. He said, "What? Do I have popcorn in my teeth?" I shook my head giggling at him then leaned over and kissed him. Softly at first but then with a bit more depth to it.

He responded by putting his arm around me and pulling me closer. Yep, I was horny now. We kissed for several minutes and my hands began roaming around his muscular chest and down across his tight abs. This man worked out constantly and had the most awesome six pack I have ever laid eyes on.

My hand moved lower and rested it on his already bulging cock, while my other hand caressed the back of his neck and hair line. We continued kissing so passionately, as a small sound of pleasure from me escaped into his mouth. I tugged the button of his trousers open and unzipped his fly, then moving my hand inside and finding his now very erect cock.

I backed off our kiss, grinning and said, "Hmm, someone is happy to see me." He grinned shaking his head yes and we went back to making out hot and heavy. I pulled his cock out and openly stroked him, its massiveness looking like a power pole in the low light of the theater. He groaned into my mouth as my finger dipped into his little opening, and feeling his juices already beginning to leak from him.

I pulled away from his kiss and lowered my head down to taste his sweet fluid. Pushing my tongue into his orifice and then stringing the precum out. Brad gasped, "You really know how to drive me crazy, woman." He ran his fingers through my hair as I licked around the thick purple head, then kissed the tip of him and began pushing his thickness slowly into my lips, taking him deep into my mouth and sucking on his gorgeous throbbing cock.

I loved the taste of him, even though I had no other cocks before to compare, I knew that his was already the best and I showed it by how much I loved it in my mouth. I made love to his manhood with my mouth and thanks to expert coaching from Carly and Miranda, I had gotten exceptionally good at it, too.

Moving my lips up and down on him, then taking the time to lick all-round the head, finding his extra sensitive spot just below the backside of the tip. He shivered as I traced my tongue around that spot then pushing him back inside my mouth and taking him all the way down as deep as it would go, my gag reflex now long gone with plenty of practice.

His pubic mound pressed against my nose and my tongue darted out to touch the top of his ball sack. Brad threw his head back, holding a hand over his mouth to muffle his pleasure. I withdrew slowly about halfway then went deep again grinding my face into him, feeling his cock push down my throat.

I backed off him again to the very tip and started massaging his thick meat with my hand, squeezing out more of his sweet precum and licking it all up. I took him back into my mouth and began moving up and down, my hand working in unison to please his masterful cock. His breathing became heavier as he moved with me, his hips providing just a small amount of push with each stroke. I knew what was about to happen and I moved a bit faster.

He covered his mouth again, stifling his groan as he pushed deeper into my mouth, I felt his manhood pulsing against my lips, so I moved my hand away and took every single inch of him all the way in, just as the tip once again found my throat, he erupted. His cum going straight down as I kept him lodged deep in my gullet. Over and over with each pulse, another jet of his hot cum found my tummy. I had to back off just a little so I could breathe, moaning as he continued his intense orgasm inside me.

As he began to finally come down, I kept sucking him and then slowly back off a little, sucking then back off, and using my hand again to help milk every drop of his love from him. Finally backing off to the tip, another squeeze produced the last pearly cum drop from his now softening cock. I licked it again just for good measure causing him to jump.

I loved it when he became oversensitive after cumming. I looked up into his eyes with a sexy grin. He smiled back then leaned in and gave me the sweetest kiss. It was perfect timing, too, as the movie was just about to end. He buttoned up and we made sure we were both presentable as the theater lights came on.

We looked at each other and laughed. Brad asked if I wanted to go back to his place for a few drinks and whatever else we wanted to get into. I giggled and of course I said yes, thinking about how awesome he was going to feel in my ass again.

We arrived at Brad's place, and just before we got to his apartment door, he told me that he had a friend from out of town staying with him for a few days and hoped that I would not mind. "Why would I mind, Brad, it's your place," I replied. He said, "Well I did not want you to be put out that we would not be totally alone."

I looked at him through squinted eyes and grinned, "Well let's just see who it is, and maybe they want to play, too." Brad chuckled, wrapping an arm around me, kissed me on my forehead and patted my ass, "That's my girl." Brad opened the door and just off in the dining area, walking towards us was a gorgeous tall thin, dark skinned black man in nothing but a pair of work out shorts on.

I could see every muscle glistening and rippling on this fine man's body. He smiled and said, "Oh hey Brad, I didn't know you'd be back this soon and hello, you must be Ms. Dawn, so good to meet you, I'm Donte." He came over and shook my hand gently. I felt my body start humming from the sexual energy this man gave off. "Nice to meet you," I squeaked out. Brad laughed a little, knowing I was completely mesmerized by Donte. I turned to Brad and wrapped my arms around him and whispered into his ear, "I want." He laughed again saying he thought I would.

We moved into the living room, and Donte excused himself to go take quick shower since he just finished working out. Brad made some drinks for us, and I literally chugged the first one down, just to calm myself a bit. This night was going to be fun; I could tell.

Brad got me another drink and handed to me, leaning down, and kissing me softly. "I hoped you would like Donte, because when I told him about you, he seemed excited to meet you. I hope you are comfortable with him, Dawn, because I think it would be a huge turn on for the three of us to enjoy each other," he breathed in my ear.

I nearly wet my panties at his words. I turned and kissed him deeply for several minutes, then pulled back grinning and slowly shaking my head yes. Brad smiled back and sat beside me. A few minutes later, Donte came out from taking a shower. He paused in the doorway as Brad and I turned his way.

He did not have a stitch of clothing on as he stood there smiling at us. My mouth dropped. Not only did this man have a gorgeous body, but his cock was a masterpiece. He was not even fully erect, yet it hung down at least one third of his thigh, and I could see the veins starting to pop out as it firmed up.

I motioned him to come closer. He moved towards me grinning knowing I wanted him. He came close, I reached out and wrapped my hand around his hot flesh. He let out a little gasp as I slowly stroked up and down this massive manhood in front of me. Brad moved closer to me to get a good view of my reactions.

He put his arm around me to reassure me. I lifted Donte's cock as I stroked it looking at the opening of the mushroom shaped cock head that was dead staring me in the face. I had to taste him as I leaned in and kissed the tip of him, then opening my mouth and taking it in a little. He sighed heavily. My lips opened a little more taking just the head in. I moved my tongue around it, just tasting him and feeling him swell even more in my mouth.

My hand moved up and down his silky-smooth organ as I back off him. A bead of precum formed at his opening and I quickly licked it off. Oh my God, he tasted so fucking good! I have to say, I though Brad had the most gorgeous cock, but this man's cock rivaled it, although I would never say that out loud. I stood up and took Donte by the hand, then Brad's and said, "Shall we take this to the bedroom?"

I led both men to the bed, pushed them to sit, and then started removing my clothes, giving them both slow erotic strip tease. First my top, revealing a lacy black bra under it. Then unsnapping it, shrugging it off and revealing my two small mounds, my nipples standing on end. Both men smiled and gave a little whistle.

I leaned over and kissed them each on the lips, just hesitating on each and slipping my tongue inside their mouths. Then backed off and continued my striptease. I unbuttoned my jeans, then moved the zipper down slowly, grinning at them and blowing kisses to keep the tease going. I was feeling so naughty inside.

I pushed my jeans down across my thighs leaving my matching panties on. Slowly took each leg off, then leaned in for another playful kiss to each of them. Donte's cock was rock hard and standing straight up. After kissing him on the lips, I leaned down and kissed his cock then stood back up.

Brad had removed his jeans and tossed his shirt by this point, his cock also standing at full attention. OH MY GOD these two men! Gorgeous in every way, and they wanted me, even if it was just for a night, they wanted ME! I shivered in pleasure at the thoughts forming in my head.

Gently removing my panties as I turned to them, showing them my ass as I pushed them down. Both men nodding in agreement their appreciation for the show I was giving them. I turned towards them and bowed as they clapped for my show. I giggled and pounced on them.

Now I am barely 140lbs, but those two acted like I was a pro wrestler coming in on them, as they fell back like I just won the championship. I could not help but laugh out loud at these two silly men. They laughed too, then turned their attention on me. I laid face down my head to the side as they kissed and touched me all over.

I was in heaven as they bathed me with their attention. Brad started to kiss around my ass then spreading my cheeks to gain access to my rosebud. Donte leaned in and kissed me passionately and he reached under to massage my breasts, circling a nipple with his finger, then moving to the other. I moaned into his kiss, just as Brad found my opening with his tongue and pushed it inside.

Oh my GOD, my body was on fire now. I reached down and grabbed Donte's cock, pulling him up to my face, opened my mouth and engulfed his gorgeous prick. I had to suck this man and suck him I was going to do! I moved his hot flesh in and out, savoring every thick vein of it as it throbbed. I swear it got even bigger!

My lips were stretched tightly around it as he began moving in and out of my mouth in time with me. I felt Brad move up behind me, his fat cock parting my ass cheeks then pressing against my opening. he pushed a little and my ass welcomed him in like a well-used tool as he slid all the way in.

I let out a long groan into Donte's cock as Brad pushed as deep as he could go. Donte then pushed his cock slowly deeper into my mouth, my eyes widening as it entered my throat. I was not very prepared and gagged just a little. He paused to let me gain my bearings, then my throat opened and accepted him fully, his heavy balls resting on my chin.

DEAR GOD, I WAS LIKE A PIG ON A SPIT BETWEEN THESE TWO MEN AND THEIR HUGE COCKS! I was in heaven, as Brad started fucking me with abandon, driving himself in and out of me. Donte fucking my mouth like it was a well-used pussy, and all I could do was grunt as each man hammered home.

Over and over their man flesh piercing deep in my little body from both ends as they got in sync with each other. One would push all the way in as the other was pulling out. I could not even move at this point as my body just took their pounding. Donte moved faster and his cock began to throb even more.

Brad matched him as they both groaned with their impending orgasms. I was on cloud nine, my own body shaking as I felt myself losing it, then went into spasms as these two continued to impale me between them. I came so hard that I nearly blacked out. Donte pushing deep in my throat and unleashing a fire hose cum shot that slapped me back to reality.

Then in the next instant, Brad slammed home and cried out as his cum began filling my insides. I swallowed as fast as I could gulp, trying to keep up with the powerful pulses of Donte erupting cock. I was being filled from both ends and once again, I thought I would drown in cum. Brad collapsed on me as his climax wound down just as Donte slowly withdrew himself from my gullet.

I could breathe again. His cock slid out of my lips along with a heavy trail of his cum, my mouth too exhausted to even try to keep it in. I felt Brad soften and slowly slip out of my ass. Oh my God, I felt so empty suddenly! Brad grabbed a towel for me and put it between my cheeks then laid back against me.

Donte moved down beside me and now I was sandwiched between these two gorgeous men. They held me in their arms and nuzzled me all over with little kisses. I smiled as the post sexual euphoria enveloped me completely as I nodded off into dreamland.

A short time later, I felt Donte move away from my side. I opened my eyes and looked up at him, still in a daze and smiling. I scanned down his body and his gorgeous huge black snake of a cock was rock hard again. He leaned down and kissed me saying, "I have to have some of that sweet ass of yours now." I nodded yes but any words escaped me.

I looked over at Brad and he was sound asleep. I looked back at Donte again, as he applied a generous amount of lube to his thick member. All I could manage was a lazy sounding moan when he mounted me from behind. I felt his cock probing around between my ass cheeks and I moved it up a little, so he had better access.

His fat cockhead found my entrance and he pushed home. I groaned long and deep from my insides as he sank deep in my gut. He grunted as his balls pushed against me and he paused there. "Fuck, Baby, your ass feels fucking amazing wrapped around my cock," he moaned. I looked back and grinned as my breathing became very ragged.

Afterhours22
Afterhours22
1,129 Followers