The Alpha Who Made Me a Sissy Ch. 02

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Relationship takes the next step.
1.5k words
36k
35

Part 2 of the 2 part series

Updated 06/08/2023
Created 07/23/2019
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Chad texted me a few days after our first encounter and I was super hesitant to return his enthusiastic messages to see each other again. I was racked with feelings of confusion and shame. Was I gay? What will my life be like? I really didn't know what to think or what I was feeling. But he persisted at easing my apprehension and I finally agreed to meet for a couple drinks.

His chilled out demeanour at the quiet pub I chose actually made things really easy for me. He didnt come on too strong, nor did he push talking about our encounter much. He made everything easy. Including wanting him again. And jesus, he was sooo cute. 6'2, green eyes, blond hair and slim but muscular frame. These girly thoughts kept persisting when I was around him. I've always been a bit of a binge drinker, so we both got very drunk very quickly and any pretence fell away. With too much money spent we headed back to my place for some "drinks I had in the fridge", but we both knew the real reason. And I was too drunk to care or fight it. I wanted him again. He was sexy and hot and I needed him on top of me.

Inside my door, I gave up my coy act and I submitted to this sexy man. My comfort in the bottom role came so natural with him, and I had his strong naked body on top of me in minutes In my bed as we made out and i stroked his thick perfectly cut cock. Although I again denied any actual Sex as I still didn't think I was truly gay, or wouldnt admit it to myself anyway. I didn't just give him another blowjob, I actually allowed him to fuck my mouth. As we kissed and explored each other bodies, He began pushing me lower while raising his torso over me and I quickly recognized what was happening, but I didn't object as I knew it would please him and I was lost in the moment anyway. It felt so naughty but I quickly grabbed his shaft and took his cock deep into my mouth with his full body over top of me. I was his bottom and I knew it. I let my hands fall away and allowed him to thrust deeper and fuck my face. It was a bit deep at times and I choked, but his stiff shaft tasted so delicious ramming in and out of my hungry fag mouth. I laid back and grabbed his ass cheeks and allowed him to completely dominate me until his familiar ropes of cum filled my mouth. Not allowing me to go another encounter without ejaculation, he didn't care about the vestiges of his delicious cum still lingering in my mouth and he kissed me deeply and jerked my hard penis gently as we grinded until I came in his hand. It was so satisfying and we feel asleep immediately in each other arms.

I woke up the next morning after a peaceful deep sleep in his arms. He kissed me on my cheek as he left and I laid there wishing he had stayed. I had allowed him to cum in my mouth twice and wanted more. I was gay for him and couldn't stop thinking about what his cock would feel like in my virgin ass. How much Would it hurt? Could I ever go back if I took that step? At that moment I didn't care and needed to find out.

I hadn't stopped thinking about it for days and decided I would take actions into my own hands this time instead of waiting for his text. I was ready and wanted him to take My virginity. My text was simple. "Hey, come over tomorrow night. Bring a condom" he answered in minutes "I'll be there after work at 10"

Holy fuck This was actually going to happen! Of course I could still back out but every time I thought about changing my mind, I remembered how wonderful his cock felt in my hands and mouth. My ass was just the next logical step right?

Class the following day was unbearable and it dragged on. As did the evening getting ready for what was to come. Minutes seemed like hours. I wanted him so bad. After a brief text, he was at mine right at 10. I drank a few beers to loosen up, but when he showed up he was happy to take his time. tried my best to act casual and offer him drinks and small talk. But He could tell how nervous I was and put down his drink and said he had something better for me than booze. He brought out some amyl poppers (I had heard of them before so I wasn't terribly concerned. And I trusted him) He kissed me and reassured me that it was all gonna be fine. I inhaled the drug and immediately felt dizzy and euphoric. But quickly totally relaxed and wanting to fuck. I wanted his cock immediately.

We kissed and fumbled to the bedroom and he took over as usual. He pushed me to the ground on to my knees. It felt aggressive, but I was his bottom and This is how it worked between us. I dutifully undid his jeans and pulled out his cock. As it stood erect in front of my face, I kissed it lovingly and It was all mine. I took it in between my lips and engulfed it as deeply as I could while he groaned. "God you're good at that baby. You were born to suck my cock." and I knew he was right. I sucked and deep throated his delicious cock while massaging his balls for a few minutes, but while I had already learned to love sucking cock, I couldn't wait any longer. I needed him inside me.

My clothes fell away as I got up and I pulled his strong body on top of me as we intertwined on my bed. He kissed me slowly and our cocks meshed as one as we grinded into each other. He spread my legs and I instinctively recoiled, but His reassurance was soft and sweet and he said he'd go slow. His words were like butter. I could never say no to him. So I raised my hips slightly allowing him access to my virgin rosebud. He quickly slipped on a condom and positioned his cock head against my ass and stared me directly in the eyes as he gently pushed. This was really about to happen. It was slight pain but nothing really until his head passed the first obstacle. A jolt of pain flooded through me and I almost stopped him. But he kissed me and waited. He kept his reassuring words how hot I was and that I'd love it soon while his mushroom head sat inside me. He gently pushed further and further and I felt so full. His cock was 3/4 in my ass!! With every millimeter deeper he'd kiss my neck and raise my legs higher. He intended to fully fuck me and I didn't want him to stop.

The next few minutes were blurry from the drugs but as the pain subsided, I realized he was all the way in and slowing thrusting in and out. I was having anal Sex with a man!! No, strike that, a total stud. As we fucked he whispered that I belonged to him now. And I knew I did. "Yes chad, I'm yours. Take me" as I wrapped my arms around him kissed his strong chest and spread my legs further allowing him all the access to my ass he wanted. He made love to me for ages and I enjoyed every second of being taken. He grunted like a man and I took his cock like a woman. I even found myself moaning and making little girlish squeals as he thrusted deep into me. I was his bitch and I loved it . When his pace quickened and I could feel my man tensing, he grabbed my penis and started jerking so we could cum together, but I said I was fine. I was more than happy with just his cock inside me... Do you wanna cum in my ass or my mouth I asked? A question I knew All good bottoms should ask. As tempting as my soft mouth was, he told me he wanted to Cum in my ass so I could feel his juices and he could mark his territory. And when he did, his wet cum stuck in in my ass for hours. He had marked me.

After pulling out and relieving all that pressure inside me, I felt exhilarated from what I had just experienced, but also very empty. Like I wanted him back in. Laying there in each other's arms we chuckled and he said the moment he met me he knew I'd be his bottom. Those thoughts drifted and we fell asleep until another frantic sex session in the middle of the night. My legs on his shoulders as he took me and fucked my no longer virgin ass. And I gave it all up to him and let him use me all night like I knew he would Many many more times.

I couldn't wait...

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14 Comments
AnonymousAnonymous10 months ago

Oh! How I wished I had been his Gurl! Now there isa Man I could live with, and adore!

His Miss Roxanne

AnonymousAnonymousabout 1 year ago

I’m such a sissy girl

AnonymousAnonymousover 1 year ago

Oh, honey, it made me want to belong to a good man even more! I want to be his wife!

Mrs. Roxanne Lanyon, Sissy Wife

mcanoe84@yahoo.com

AnonymousAnonymousabout 4 years ago
Fun Story....

Not sure how the condom blunder happens if you edit and proofread your work!?! Aside from that, the story for me was enjoyable. I like stories when I can identify and think of myself as one of the characters. I've been with men and had that wonderful feeling that the man wants me to be the total bottom and be as feminine as I want. It is special... "he grunted like a Man and I took his cock like a Woman"... or "I was his Bitch and I loved it"... That is the role of a Good Sissy!!!

AnonymousAnonymousover 4 years ago

This was mildly similar to my first lover, except I was 18 and he was 34, and we never made it to the lipstick and lingerie like we wanted. He had to move away with his job.

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