I thought I knew myself

I married at 20, and was married for 8 years. We had a wonderful life and an even better sex life. She used to give the most amazing blowjobs, even introduced me to anal/prostate play. Stroking and sucking me while stimulating my prostate, edging me for 45-50 mins before greedily sucking me to completion. But this isn’t a story of back then, this is a story of now.

I’ve been divorced for 3 years now, and loving every minute of my new life. Let’s dive into the night/nights that led to my divorce and subsequent new life. My wife a traveling nurse would be headed to Oregon for 3-4 weeks. The first night I masturbated 2-3 times but without the prostate play, the orgasm just wasn’t right. I started going through our chest of toys and outfits. We had all sorts of toys for her and I, so it was just a matter of what caught my eye. A vibrating butt plug, the anal-ez lube, and a flexible dildo. As I moved things around my pulse quickened when I saw the Mr Marcus dildo. I remember how lifelike it felt when I stretched her out with it.

I was eventually able to get the dildo in, but while trying to achieve orgasm I pushed it out ruining the orgasm. I popped the vibrating butt plug back in and jerked until I came. But the next morning I was disappointed in the orgasm once again and got the dildo out, I suction cupped it to floor and rode it to a hands free orgasm. I think that’s when it sparked in my mind, and that night I found myself watching gay porn with the butt plug in. As I was about to go back to riding Mr Marcus I saw a young guy very similar in build in a thumbnail. Sissy takes first bbc. I clicked it and lubed up the dildo. My curiosity was burning now, dildo still deep in me I moved the App Store and downloaded grindr.

I stood up and the dildo plopped out of my ass. I showered and shaved and got ready. Almost as if I was possessed, I knew I exactly what I needed to do. I went back the chest of toys and got an outfit too big for the wife. Thigh high white stockings and a plaid skirt, with a white top that had no shoulders and an attached faux tie. In the closet was a demon slayer wig from the prior Halloween. Pink and green pigtails. I helped her do her makeup for that Halloween so I proceeded to try my luck. I looked like a joke. So I went to YouTube and found a tutorial to help soften my features. I achieved a very feminine look minus the lack of blending it in. I slipped on the wig and took a look at myself in the mirror. Clearly still a man, but oh did I look fuckable.

I made an account and made my username femhost looking. My display photo a shot of my legs in stockings.A lot of the people were just talkers that just wanted a photo and disappeared. I kept refreshing and sorting by distance, and I saw a thumbnail of a bulge in some white underwear. The white of the underwear a sharp contrast of the dark black belly and thighs. I clicked on his profile, 55 yrs old, black and 6’2. Looking for throat and ass, fem only. I was nervous, I couldn’t bring myself to start a chat. When he messaged me. Straightforward and to the point, he asked how my night was and sent an album and asked for pictures. Good, I replied. I explained I don’t have any, but will take any photos he wanted. He explained he wanted a full body shot, and one of my ass. I setup the camera and did a few takes for a full body, and an upshot of my ass in the skirt.

I clicked on his album after I sent 2-3 photos. The first was the same underwear as the thumbnail, only pulled to the side. It was glistening from whatever lube he was stroking with, and so fat. It was laid on his thigh, not hard but not soft. I couldn’t tell how long, but it looked big. The next it was completely hard and the massive head and girth really stood out. I was actually nervous now. This looked as big or bigger than Mr Marcus. The final slide had a Comcast remote for scale and I then knew he was definitely bigger than Mr Marcus. “Damn baby, I’d like to get up in that pussy. You like what you see?” He asked. I almost closed the app and deleted it, I was very nervous and questioning what I was doing. I shifted my weight and the vibrating butt plug made my prostate tingle and I double tapped his photo. I love it daddy. I responded.

He asked what I was into and told him I had only played with toys so far, but loved the feeling. He wasn’t sure I’d be able to handle him and didn’t want to waste either of our time. I assured him I wouldn’t quit on him. I popped out the plug and found Mr Marcus. I slide it back inside me and clicked record and began popping Mr Marcus all the way out and all the way back in. I sent the video and waited. “Alright baby, let’s meet up then, where you at?”
I hesitated as I typed out my address, the urge to back out was back again. I hit enter. Fear flooded me again, when I saw 5 mins away. See you in 10, gathering up some things.

It dawned on me I had never tried out a feminine voice, this has all been in text. Make believe was slamming into reality as I had no clue how long til he was here. I felt so stupid trying out different lines at different pitches. Mmhmm yes, please daddy, fuck me daddy, I moaned like a bitch and tried out a whispy soft fuck me daddy. I opened the chest again and pulled out my wife’s fox tail plug and slid it inside me. Mmm I purred, and walked toward the window overlooking the parking lot. As I looked I felt my phone buzz, he was here. I told him to head up the walkway. I would crack the door. My heart felt like it would beat out of my chest. The door gently swung open and in he stepped, closing the door behind him.
Can I get you something to drink I asked in my best submissive slut voice.

Nah, get over here, he commanded. His voice so deep and powerful, I instinctively walked over to him. I wasn’t a tall guy by any means, but I never felt small until in front of him. He placed his hand on my cheek, and moved my face to look at him and closed the distance. Kissing me deeply, probing my my mouth and tongue with his. Lost in the moment I passionately kissed back, tracing my tongue on his. His large hands exploring my body, firmly gripping my ass. He felt the tail and stopped kissing me, he spun me around and pushed me up against the back of the couch. He popped the plug out aggressively, leaving a slight burn from its quick removal. But this was replaced instantly with a tongue exploring my hole. I moaned as he ate my ass and purred out a yesssss daddy. He turned me back around and kissed me. I could taste my hole on his lips. I was so hard at this point there was no hiding it. My skirt was flipped up. “Awww my girls little clit is hard.”

He proceeded to give me a fast paced blowjob while probing my ass with his fingers. I didn’t last long, as this was exactly what I missed from my wife. My horniness level dropped after he sucked every last drop out of me and stroked well after I had cum. I was thinking how I could back out of this, when he came back up to kiss me and I tried to just kiss him with a closed mouth but he aggressively squeezed the back of my neck and I let his tongue enter, and with it came all my cum. Swallow it he commanded. I felt nauseous, as I swallowed it. Before I could draw any objections I was presented with his large floppy cock. “Let’s head to the bedroom baby”
Yes daddy I replied and walked him to the bedroom.

He grabbed Mr Marcus and had me lay down on bed, he presented a glass vial to me and told me to breathe it in. I wasn’t sure what it would do but I did as he asked. I took his cock into my mouth and moaned while sucking him. It took form in my hands and mouth, and he began fucking my ass with Mr Marcus hard. I squealed as he pounded my ass with the toy. There wasn’t any pain, only ecstasy as he plunged the toy deep into me. Oh god oh god oh god, yes yes fuck meeeeee daddyyyyy. I let out. It abruptly stopped and he slid the toy out. He pulled out a cock ring and placed it at the base of his engorged cock. He moved me to my belly and pushed my legs together. Straddling my legs I then felt it. His fat cock against my asshole, I quivered and pop. He popped the head in and out a few more times. Then slid until his balls rested against me.

Unngh I moaned as his pace slowed to long deep slow strokes. As my orgasm built back up my moans intensified, as I came his pumps became a jack hammer. He fucked me hard and deep as my orgasm rolled. I screamed as he relentlessly fucked my hole. Yeah give daddy that pussy. Grunts and short screams were all I could get out as he fucked me into the mattress. He had me suck on it for a while to catch his breath. His second wind didn’t last that long, and when he got close to cumminy he ripped out of me and came into my mouth. It was so much cum I gagged and sputtered. He forced me to eat every bit I dropped, and took me to the shower.

He took off all of my outfit and makeup and washed me in the shower. So delicate and gentle was his touch, a far cry from the man who just thrashed me on the bed. We got clean and climbed back into bed. He cuddled up to me and I fell asleep. I awoke to him guiding my mouth to his cock around 2am and we did a lazy side fuck and went back to sleep with his cock inside me. He ravaged me hole the next morning like the night before, but filled me with some cum this time. We would meet several times after that, and I’m still with him today. My days start and end with worshipping him, and I can’t believe I was ever straight.