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Chapter 3 The Engagement

Continuing saga.

Spankmasters
Jul 19, 2024
5 min read
gay romancegayChapter 3 The Engagementcross dressingtransgender
Chapter 3 The Engagement
Chapter 3 The Engagement

Chapter 3 The Engagement

Almost 6 weeks had passed, since that first wonderful weekend I met Jim. Things between Jim and I were going well.

It was the weekend before my twenty eighth Birthday. Jim had made reservations at a nice restaurant. So when I got home from work I showered, and put on a nice outfit, which consisted of a white pleated mini skirt, heels and a flower print sleeveless tie top blouse. It showed my navel, but not much more.

He picked me up and we went to dinner. After dinner we took a walk on the beach. The sun was setting, it was bright orange as it seemed to sink in the sapphire blue gulf water. We sat on a bench on the boardwalk and admired it. We kissed, Jim said we needed to talk. I asked him what was on his mind. He began to tell me his plan.:

"I've been thinking...I want you to move in with me. I want you to be my wife.

I was surprised as he produced a ring box with a one karat diamond solitaire engagement ring, in a platinum setting. I was even more surprised by the black leather collar adorned with gold and diamonds.

"Be my wife Baby, wear my ring and collar."

He slipped the engagement ring on my finger as I said "yes," and kissed me as he put the collar on my neck.

"When we get home I have some birthday presents for you to open."

As soon as we arrived at his place, he instructed me to go to the bedroom and strip down to my lingerie and come to the living room. I did as he instructed.

When I came into the living room, I saw several boxes of different sizes as Jim chirped:

"Happy Birthday Baby...Come on, open them!"

He handed me a large box. As I opened it I realized it was a "Sling." I continued to open each box, as more similar themed items emerged from the boxes.

There were a variety of hand cuffs from fuzzy to chrome. Ball gags of different sizes. Two pairs of thigh high stiletto boots, one black pair and one white pair. A chastity belt, with a butt plug big enough to qualify as a dildo, and a thick stainless steel torso chain with chrome loops for the leather wrist restraints. There were a few dildos of various sizes, and nipple clamps. He handed me a small box, as he displayed a proud smile.

"This will look good with your bikini."

It was a 14 karat gold herring bone belly chain. I was speechless, as I held up the items and looked at them, wondering what I had gotten myself into. I thanked Jim for the presents. I hesitated, but pressed forward, with the thought, "You just have to try."

Just then, I heard Jim say.:

"Try the black boots on Baby. I want to see you in them with your black lace panties and bra."

"Yes Daddy."

I put the thigh high boots on, They fit perfectly and the black leather shanks fit snuggly around my legs and thighs. I stood up and turned in a circle as Jim approached me.

He wrapped his big masculine arms around me and began kissing and sucking my neck as his finger probed my navel, I could feel his big cock getting rock hard, as he pressed it against my ass!

He was still wrapped around me, as he guided me to the bar that separated the kitchen and living room. The six inch heels gave me the height to be at a comfortable level for me to bend over the bar, and placed my ass directly in front of his crotch.

He was kissing my neck, caressing my body, whispering in my ear how sexy I looked in the boots. His finger was probing deep in my navel as he pulled my panties down just enough to get his big cock in me.

He guided me to bend over the bar. I could feel his cock, wet with precum, spreading my ass cheeks as he rubbed it up and down on my sphincter.

While Jim and I had been dating for about six weeks, We had still only had sex a few times. It got easier each time, but I could still feel every solid inch. Especially when he was all the way inside me, pushing my navel up from inside.

He gripped my hips as he suddenly thrust the entire length of his massive cock inside me, and began pumping his hips violently.

I squealed and screamed loudly. I was squirming and breathing erratically as I moaned:

"Oh god Daddy, what are you doing, why are you being so rough?"

He had me pinned against the bar, his grip on my hips tightened and his finger probed deeper in my navel as he grunted while fucking me.:

"You accepted my ring and collar, you're my girl now! You're going to learn what that means. You're going to get used to my big dick and I'm going to fuck your sexy ass anytime I please!"

I could barely hear what he was saying as he fucked me. I was lost in the pain and ultimate pleasure I was experiencing!

My climax was growing as I panted and moaned. My tiny cock was hard and leaking cum. My tightly stretched sphincter was gripping his massive cock, and I could feel his long strokes poking my navel from inside as he pumped his hips. His aggressiveness aroused me to orgasm.

He knew he had already made me cum, but he continued fucking me. I was gasping and moaning, screaming and squirming as he poked my navel and gutted me with his massive cock. I was quivering, I could feel another orgasm growing inside me.

I heard his heavy breathing as he began to tense up, his thrusts were deep and violent. Suddenly he yelled.:

"Oh fuck Bitch, I'm gonna seed your ass!"

My second orgasm exploded out of me, as he shot his thick hot load deep in my tight ass.

He slowly pulled his cock out of my cum soaked throbbing ass, and turned me around to kiss me. He forced his long hard tongue deep in my throat. I sucked his tongue, as I reached down and began stroking his massive cock as we kissed.

When I began feeling it getting hard again I knelt down on my knees and looked up into his beautiful piercing blue eyes. I took his meaty cum soaked cock into my warm moist lips and began sucking purposely and enthusiastically. By now, I knew exactly what he liked when I sucked his cock, where he was most sensitive, and how to make him rock hard, and cum.

It didn't take long before I was drinking his thick hot cum. He loved that I always swallowed his cum whenever I gave him a blow job. He dropped to his knees and held me as we kissed, sharing remnants of his cum. Then he positioned me on my hands and knees, to fuck me again.

In Chapter 3 The Engagement, Jim surprised you with a request for you to move in and become his wife, proposing with a diamond ring and a black leather collar. As part of your birthday celebration, he revealed a collection of BDSM-themed gifts, including cross-dressing items like thigh-high stiletto boots and a chastity belt with a dildo-sized butt plug.

During the intimate moments that followed, your relationship took on a new dynamic, with Jim expressing his desire to assert his dominance and you agreeing to explore the role play. The cross-dressing elements, such as the black boots and lingerie, became an essential part of this new dynamic, adding an extra layer of excitement and arousal to your encounters.

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