I have finally fulfilled a long dream of enjoying a man while we both wore stockings and knickers. He answered an advert I put on Craigslist which read as follows:
Stockings Loving Male - m4m - 50 (Leeds)
Age : 50
Body : curvy
Height : 5'8" (172cm)
Status : divorced
Likes : Non Smoker
He got in touch and we arranged to meet at his home. I arrived carrying a few items in a bag that we made use of later in the bedroom. Initially, we chatted in the lounge about general things, then gradually the conversation got more sexual and we talked about us wearing stockings. He removed his jeans and revealed lovely stocking-clad legs. He also revealed that he was wearing peep-through men's lace knickers and his long cock was hanging through a long way down one leg. I could hardly take my eyes off his cock as we continued to chat. He moved nearer and got close enough for me to touch his cock. I reached out and put my fingers around it and immediately began sucking him. It was wonderful, feeling a cock becoming more and more aroused in my hand and mouth. He became quite hard and moved to lay back on the sofa with his legs apart, while I continued to give him head with my mouth and stroke his balls with my fingers. He started to pant and I got very aroused myself. So much so that I started to deep throat him while he watched, slowly lowering my head over him and taking his long cock deeper into my mouth until it was pushing down and then inside my throat. I managed not to gag and slowly moved my head back and forth so that he had a lingering experience of warmth and motion in my mouth. I also flicked my tongue rapidly over the head of his cock while he was just inside my mouth. Then I moved down on him again in full deep throat and started to slowly bob my head up and down, giving him repeated deep throat fucking and only moving my head up again when I started to gag and needed air. He was gasping now and I could taste his pre-cum as I licked the head of his cock, so I slowed down a little and concentrated on stroking his balls with my fingers and licking the side of his cock with my tongue. I asked him if it was OK and he said that it was very relaxing. I looked at his cock, it had changed colour and was vividly redder than before with the veins prominent all over. He was definitely very aroused. When he had calmed down a little, I started to deep throat him again but as I moved my head very slowly back up again I put my thumb and fingers around his cock at the base and followed my mouth up his cock with my tightly gripped hand, all the while now sucking strongly on his cock; effectively 'control wanking' him while fucking him gently with my throat. He loved this and started squirming on the sofa. I repeated this four or five times but always slowly so that he did not come. Then I took his cock out of my mouth and just stroked it while we talked about sex.
We moved up to the bedroom and I carried my bag up with me. In it I had a towel, two bottles of Super Slik anal lubricant, two lubricant applicators (to squirt the lube directly inside my anus) and a number of Extra Safe condoms. I took these items out of the bag and it would have been obvious to him that I was ready for full anal sex if he wished it. We lay the large towel on the bed above the duvet and I took off my outer clothes. Underneath I was wearing tight G-string panties and black Fiore 20 denier hold-up stockings. We lay on the bed side by side and I resumed sucking his cock while he lay relaxed with eyes closed. We were both getting very aroused. I let my fingers stray down to his anus and started to tease his hole with them, occasionally easing one finger inside him just a little. I stopped when he said "Naughty", at which he got up and asked me to follow him to the bathroom. He showed me how to give myself an enema with the shower hose (with the shower head removed) by turning the shower on and setting the water nicely warm (but not too hot), then holding the shower hose tightly against my anus and allowing the water to flow up inside me until I felt full. Then to remove the hose and sit on the toilet, evacuating the water and other material out of my anus. We did this twice each, then we both filled ourselves with water again and held it in for at least five minutes while walking around and talking. Finally we both evacuated ourselves and cleaned up, before returning to the bedroom. I have used this enema technique ever since but with five enemas each time before the final 'held inside' enema and now with a shower enema attachment (complete with On/Off tap) to screw onto the shower hose.
He lay on the towel and I started giving his now flaccid cock some very strong sucking, getting him nice and hard again. I pumped some of the Super Slik lubricant onto one of my hands and, while I continued to suck him, I slowly teased his anus with my fingers and then fully inserted my right index finger right into him. He raised his bottom briefly off the towel, pushing his cock deep into my mouth, while I pushed my finger firmly all the way into him. I moved my body between his legs and began a continual process of finger fucking him and deep throating his cock. After a few minutes of this he folded back his stocking-clad legs, making it obvious that he wanted me to fuck him. To confirm this, I moved up and teased his lubricated anus with the tip of my cock. He did not resist, so I leaned over to the bedside table to get a condom and put it onto my cock. Then I pumped some Super Slik lubricant onto the palm of my hand and rubbed it onto my very hard condom-covered cock. When ready, I resumed teasing both his cock and anus, while he lay there on his back with his knees folded up near his face. Then I raised myself up above him and presented my 'anal virgin' cock to his anus. We both helped to ease my cock into him, myself being very gentle so as not to hurt him. Gradually my cock got further and further, deeper and deeper into him as I lay on him with my arms and shoulders pushing his stocking-clad legs back into an anvil love-making position. My cock was deep now, inside him to the hilt, and I began fucking him, slowly at first, then ever more quickly as we both got extremely, pantingly aroused. He urged me to fuck him harder and I did not need any encouragement to fuck him as fast and as deep as I could. For at least five minutes (I can last a long time when in a condom), I fucked him at full pace, before climaxing gruntingly to an 'anal virgin' bisexual orgasm. I pumped my cum into him, held safely inside the condom, before looking at him in awe at what had just happened. My first time I had worn stockings and panties with a man; the first time that I had sucked a cock; the first time I had deep throated a cock rather than a dildo; the first time I had stroked a man's balls; the first time I had teased a man's anus; the first time I had pushed a lubricated finger into a man and teased his gripping anal muscles; the first time I had put on a condom for a man; the first time I had fucked a man; the first time that I had cum inside a man. He knew it and could see the look on my face.
I took off the condom and we talked for a while, then we both went to the bathroom to clean up. I got back to the bedroom first and filled an applicator twice with Super Slik lubricant, pumping it up into my 'anal virgin arse'. Then I lay face down on the towel until he returned to the bedroom, presenting my widespread stocking-clad legs and bare butt to him. I asked him if he would fuck me and he said "Yes". Then he masturbated himself hard with lubricant, put on a condom, rubbed lubricant onto the condom and rubbed more lubricant onto and into my anus. He got onto the towel behind me, kneeling between my legs. He pushed my legs wider, then pushed a finger into me to check if I was lubed up OK. I knew what was coming next and I braced myself both emotionally and physically for my first anal fucking by a man (I have used dildos and vibrators in the past). He could not get his cock easily into me, so he moved up closer to me and spread my legs further. I could feel his cock pushing on my anal sphincter muscles, feel it trying to enter my most intimate and deepest parts, feel it trying to take my anal virginity. He got into the entrance but then withdrew his cock. He asked me to kneel up and to put my shoulders back down on the towel, presenting myself before him and offering myself to him, allowing him to take my vulnerable virginity. Now he moved very close to my butt and I knew the time had come. His cock was now entering me with a considered urgency, slowly at first as he passed beyond my tight sissy cunt entrance, pausing to allowed me to get used to the size of him, then withdrawing a little, then entering me further. I helped him by pushing back with my anal muscles, opening myself and my sphincter up for him. He repeated the entering and withdrawal over and over again, getting deeper and deeper into me each time, until I suddenly realised that the whole of his long and large cock was inside me. We both paused while I got used to the idea of being fucked by a man. Then he gradually but not fully withdrew and started to slowly fuck me from behind while holding my butt and stroking my stocking-clad legs. I pushed back into him each time he drove his cock into me. I was becoming more and more aroused internally and externally, panting now with each of his thrusts. He was also panting and, although I could not see him, I knew that he was enjoying fucking me. He was driving his huge cock hard and deep into my sissy cunt, pushing me forward each time before I could regain balance. He was also fucking me at an increasing pace, so fast that he could not have fucked me any faster or deeper. It was exhausting for both of us but it was also extremely enjoyable. I could feel the grip of his hands on my bottom tighten and knew that he was about to cum. He was about to cum inside my 'virginal anus'. With a final flurry of very fast and very deep multiple thrusts of his pulsing cock, he came noisily inside me, pushing his cock in all the way as he jetted semen into my now no longer virginal 'sissy' pussy. I was ecstatic; it had happened. Not only had I taken a man but I had also been taken by one. The first time a man had teased my anus; the first time I had lain with my butt in the air in anticipation for a man; the first time I had felt a man lubricating my anus and exploring me with his fingers; the first time I had felt a (very large) cock trying to take me; the first time I had eased my anal muscles apart to help a cock enter me; the first time I had felt a cock disappear inside me slowly and fully; the first time I had felt a cock begin to fuck me; the first time I had felt a man grip my bottom as he enjoyed me; the first time I had felt a man fuck me hard, deep and very fast as if I was a women; the first time I had felt the anticipation of a man about to cum inside me; the first time I felt a man shudder and pulse inside me as he exploded in orgasm; the first time that I felt a sated cock withdraw from me; the first time that I had fully understood me.
He got off the bed and removed the full condom, putting it on the floor for later disposal. I was still very aroused, so I asked him if he would play with my arse for a while. He put on latex gloves, lubricated them, then inserted several fingers into me, pushing hard and deep, widening my anal entrance to the point that it nearly but not quite hurt. I started to pant and loved his attention, so he thrust his fingers even deeper and widened my anus beyond the pain barrier. I was extremely excited but could only take a few seconds of this glorious abuse before I moved up the bed away from his fingers and he realised that I could take no more. However, it had been superb and memorable.
We relaxed and chatted for a few moments, looking at his extensive 'clothes' collection of stockings, panties and lingerie. Then we both realised it was time for me to go and I dressed reluctantly before heading for the door. We had not kissed and had not embraced, perhaps leaving this for another time.
This was the most memorable experience that I have ever had in over fifty years of life; hence, my sharing this with you at length. I hope that you have enjoyed reading it on my Blog and I hope that you will encourage others to read it.
I am now, thankfully, no longer an 'anal virgin'.
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