I started cross-dressing as a child, wearing borrowed clothes and tights. I found it arousing and enjoyed it. At the same time, I also experimented with self-bondage, while 'dressed', which I still do today.
My journey through life, being a willing cuckold, watching my partner enjoy another man, included the desire to clean her up afterwards, licking and sucking his copious, salty cum from her now gaping vagina. Initially, I was allowed to push my tiny cock into her and also cum inside her, but then that too was denied. She started seeing him without me and I only got to know about their meetings afterwards, when Jayne would tease me as I cleaned her up with my tongue. That meant my desire to suck his cock, before he fucked her and later clean their coital fluids from his cock, was unfulfilled because I was no longer present to watch them and we did not progress that far.
The next phase on my long journey, was to meet other like-minded males, either also cross-dressers or later with dominant males who liked to fuck a compliant 'sissy cunt'. With other cross-dressers I could be a 'top', 'bottom' or 'switch' dependent on my meet partner(s) but, because of my small cock, I preferred to be a 'bottom' and for my 'sissy clit' to be sometimes locked up in a cock cage. Other men, cross-dressers or dominant, have sucked my cock and I have sucked theirs; I enjoyed giving and receiving fellatio, 69 and other oral positions; I could do deep throat, with a cock pushed all the way down without me gagging. I also craved to be helpless during these meets, and punished for allowing others to explore me, because now I was also being fucked in my 'sissy cunt'. To be 'dressed', tied up, bound, gagged and totally helpless while an erect cock pounded inside me and exploded into a condom or filled me up, was a wonderful experience. Then to be smacked, caned, whipped afterwards was both painful and fulfilling to my subservient mind. I remember the first time I was fucked bareback, by a man I had met several times before; on this occasion I had my hands bound together behind my back, while I lay face up on the hotel bed wearing a blond wig and makeup; my ankles were also cuffed and locked to a leg spreader, which he raised over my head to give him access while he pushed his throbbing cock slowly into me; I knew that he had not put a condom on this time but I was totally helpless to stop him as his long, thick cock took me inch by inch; when he was fully inside me, balls deep, the look in his eyes was of triumph and almost manic; he was taking me bareback whether I liked it or not, and I liked it; he took his time, gently fucking me, then gradually increased speed until eventually he was rapidly taking me as I lay helpless beneath him; he came deep inside me, spurting his cum into my 'sissy cunt' as I lay there wearing a bra, panties (pushed aside), suspender belt and stockings, high stiletto heals, the blonde wig, mascara, makeup and lipstick; I was fulfilled and on all our subsequent meets he fucked my 'sissy cunt' bareback many times. Another dominant male, with a enormous cock, liked me to come to his home and get 'dressed' in his bedroom and ensuite while he remained downstairs in the lounge, waiting in anticipation; he used to buy new clothes and shoes for me, laying them out on the bed for me to look at and put on; then I would go into the bathroom to put on my mascara, eye shadow, makeup, lipstick and perfume, also spraying the latter inside my panties for him to enjoy when rimming me and teasing my 'sissy clit'; sometimes I would wear a cock cage and then he would tease my swollen balls; he liked to hear me clip-clopping down the stairs in new high heeled shoes, touch me and stroke my stockings, kiss me and fondle my breasts, rub and squeeze my cock and balls; I used to suck his already erect cock while he sat on the sofa with his legs spread for me, so I could get nearer, on my knees before him, hovering my mouth over his throbbing cock and blowing on it, then licking and sucking it while he encouraged and sometimes forced me to do it with his hand on the back of my wig; we fucked in many different positions, with me sat on him in cowboy or reverse cowboy, him mounting me in rear entry while I was resting my elbows on the sofa, or on all fours or pushed flat onto onto the carpet, missionary when he would kiss me while I had my legs raised and spread for him; each time he would be gentle at first because his cock was huge, thick and long, allowing me to get used to him again on each visit; he would offer me poppers and he would take them himself; we would use lubricant and I would inject myself with lube beforehand; he never used a condom because he wanted to enjoy spurting into me, which he did on multiple occasions during each visit; after each climax we would rest a little while, then I would suck his cock and when he was erect he would enter me again, in a different position; we never used bondage but he was very dominant, smacking me and telling me that I was a dirty sissy, before, during or after sex; and I used to crave his cock and his dominant nature, enjoying the tremendous feeling of him spreading my 'sissy cunt lips', then entering me, and thrusting his cock deep inside me, then finally I could feel his wonderful cock exploding into my 'sissy cunt'; I miss his cock and I miss the clothes and shoes he used to buy me.
I gave all my cross-dressing items away when I left the UK and settled in Spain, but have now started to buy female items for me to wear. What I miss is the opportunity to meet other like-minded makes, either cross-dressers or dominant. This is the next step on my journey, to share a cross-dressing life, to talk and chat with others while cross-dressed and, maybe to also have a sexual experience with them. The first step is writing this, in the hope that someone reading it will contact me.
The next part of my journey has begun.
