My Anal Quest (furthest I've gotten so far)
I always knew I was a bit different though due to social stigma I didn't fully accept it till later in life. I wish I knew then what I know now and had embraced it sooner. Puberty hit and gynecomastia (formation of women's breasts) hit harder (36C). I was teased, groped constantly and was even forced to dress for a class project. I lied to myself about how good my breasts felt being groped and tried dating women. I got cheated on constantly and treated very poorly and finally in my 30's I decided for a change. I tried dressing in one of my exes things she had left at my house while she was screwing around and took some pics. I loved how I looked and how I felt increasing my self confidence.
I took an ad out on Craig's List posting the pics I took to see if anyone liked them and was astounded by the amount of positive feedback from older men. The dirty comments they made about my tits and what they wanted to do to me fueled my determination and I picked one to try and meet up with. His name was (omit for privacy) but he wanted me to call him Daddy. He was 25 years older than me, heavyset, had E.D and was married. He wanted me to meet him on a walking path nearby and to bring my Ex's clothes to change into there. He also told me to bring some Vaseline just in case and being the people pleaser I am I complied.
He was very sweet when we met and we walked up the path a ways before he told me to get changed. I put my backpack down as my heart raced and quickly changed out of my t-shirt and shorts (panties and bra underneath) and into the A-line racerback dress of my ex. He was on me like a tiger pouncing on a gazelle. His hands grabbed my tits squeezing and kneading them. He said I was to be Daddy's big titty slut from then on and pulled my tits out. He proceeded to suck on them hard causing me to lose my senses in true sissy bliss fashion. He grabbed my butt while sucking my tits pulling me closer and holding me tight. After what seemed like an eternity he stopped and asked if I was a good gurl and had I brought the lube. I replied I had and it was in my pack at which point he said good gurl cause I brought something for you and pulled a 6" dildo out of his pocket and told me I was going to take it like a good big titty slut and ordered me to grab the lube.
My mind was foggy from the attention my tits had received and I turned and bent at the waist to rummage through my pack for the lube. In an instant he pulled my panties down enough and started to shove the dildo in dry up my tight ass. In shock I tried to pull forward and he put his hand on my shoulder and held me tight telling me to take it like a good gurl. I froze in pure submission as he stuffed it to the hilt up my butt, me bent at the waist in an Ex's dress on a hiking trail with a older man holding me in place. He started pumping the dildo in me hard saying stuff like that's a good bitch and to be Daddy's slut. He shoved it all the way in hard and pulled his pants down telling me to suck him off as he positioned around to my head, hand still on my shoulder. I obediently did as I was told and his semi hard cock was in my mouth and he started to grab my tits as they hung down. It wasn't long before he was grunting telling me to swallow it all as he groped my tits. I swallowed it all and he pulled away, marveling at the sight of me. I reached around still bent at the waist and tried to pull the dildo out but to my shock it was stuck. He just chuckled while pulling his pants up and got ready to leave. I was worried as I worked on it to dislodge it from my tight sissy hole. It finally slid out and he said keep the dildo we'll have to do this again as he walked off back to his car. We never met back up but since I have craved an older man to own me like he did and get so turned on when guys calls me a big titty slut. All I can think about now is men and how badly I want to be a good gurl and serve them. Hope you readers have enjoyed my beginning to becoming a complete sissy slut for men.
I took an ad out on Craig's List posting the pics I took to see if anyone liked them and was astounded by the amount of positive feedback from older men. The dirty comments they made about my tits and what they wanted to do to me fueled my determination and I picked one to try and meet up with. His name was (omit for privacy) but he wanted me to call him Daddy. He was 25 years older than me, heavyset, had E.D and was married. He wanted me to meet him on a walking path nearby and to bring my Ex's clothes to change into there. He also told me to bring some Vaseline just in case and being the people pleaser I am I complied.
He was very sweet when we met and we walked up the path a ways before he told me to get changed. I put my backpack down as my heart raced and quickly changed out of my t-shirt and shorts (panties and bra underneath) and into the A-line racerback dress of my ex. He was on me like a tiger pouncing on a gazelle. His hands grabbed my tits squeezing and kneading them. He said I was to be Daddy's big titty slut from then on and pulled my tits out. He proceeded to suck on them hard causing me to lose my senses in true sissy bliss fashion. He grabbed my butt while sucking my tits pulling me closer and holding me tight. After what seemed like an eternity he stopped and asked if I was a good gurl and had I brought the lube. I replied I had and it was in my pack at which point he said good gurl cause I brought something for you and pulled a 6" dildo out of his pocket and told me I was going to take it like a good big titty slut and ordered me to grab the lube.
My mind was foggy from the attention my tits had received and I turned and bent at the waist to rummage through my pack for the lube. In an instant he pulled my panties down enough and started to shove the dildo in dry up my tight ass. In shock I tried to pull forward and he put his hand on my shoulder and held me tight telling me to take it like a good gurl. I froze in pure submission as he stuffed it to the hilt up my butt, me bent at the waist in an Ex's dress on a hiking trail with a older man holding me in place. He started pumping the dildo in me hard saying stuff like that's a good bitch and to be Daddy's slut. He shoved it all the way in hard and pulled his pants down telling me to suck him off as he positioned around to my head, hand still on my shoulder. I obediently did as I was told and his semi hard cock was in my mouth and he started to grab my tits as they hung down. It wasn't long before he was grunting telling me to swallow it all as he groped my tits. I swallowed it all and he pulled away, marveling at the sight of me. I reached around still bent at the waist and tried to pull the dildo out but to my shock it was stuck. He just chuckled while pulling his pants up and got ready to leave. I was worried as I worked on it to dislodge it from my tight sissy hole. It finally slid out and he said keep the dildo we'll have to do this again as he walked off back to his car. We never met back up but since I have craved an older man to own me like he did and get so turned on when guys calls me a big titty slut. All I can think about now is men and how badly I want to be a good gurl and serve them. Hope you readers have enjoyed my beginning to becoming a complete sissy slut for men.
3 months ago
