My journey part 111.
After a few minutes of this he asked if I felt ready and when I said yes he asked me to kneel in front of him facing away as it was not quite so uncomfortable in that position for the first time as I could move around more easily if I needed to do so, I did as he asked and he put more Vaseline in and around my arse hole and loads on his cock and came up behind me and steadied himself with one hand my hip using the other hand to guide his cock up and down my crack before finding my hole and gently pushing forward until I could feel his whole cock head in my arse, it was a little painful but also quite pleasurable at the same time and I began to push back an inch at a time stopping just to get used to the feeling of his cock filling me up until Matt was buried in my arse as deep as he could go and all that I could feel was a fire and a feeling of being stretched to the limit, after a minute or so he began to gently and very slowly thrust in and out of me and the feeling was wonderful and so sexy I asked if we could do it face to face like when I had fucked him so he withdrew and got a small towel and with a cushion and laid them on the bed and told me to lie on it spreading my legs as he had done, he retrieved the spunk stained satin knickers and put them on pulling his cock through the leg hole before getting back on the bed between my legs and putting his hard cock back in my waiting hole and begin to fuck me again.I cant describe how horny an experience it was feeling his body grind in to me as his cock filled me up and then the strange but pleasant feeling as Matt pulled nearly all the way out before plunging back in again, when he held my head and crushed his lips against mine before forcing his tongue in to my mouth as he opened his mouth and our two tongues danced a delicious sensual dance with his hands touching my body from my cock to my face and back again whilst I massaged his sexy arse in my dirty satin knickers it was not long before I had a huge orgasm as he did a short time later.In the last twelve hours I had gone from being a straight crossdresser to a very bisexual crossdressing, arse licking, cock eating, arse fucking slut that loved putting my fingers tongue and cock up other peoples arse holes as much as having them doing it to me and what a journey that was. Up until this point in my life I was quite inexperienced in sex with women and men never even featured in any fantasy let alone real life and at that time I did struggle with guilt and shame but one of the good things about being a young man was that these doubts and guilty feelings were quickly forgotten or justified as soon as we get turned on and or got a hard on. With Matt moving away in a few months for a new job we both had very little time to explore and play with each other so we began playing hard and fast in all sorts of kinky ways, the only thing new I had brought to the table was wearing knickers and Matt admitted it turned him on both seeing me in knickers and wearing them himself so he asked me what lingerie I had and if I could bring it to his flat for us both to play in so that day I packed all that I had in my back pack except for one short satin night dress and a matching pair of French knickers that I had bought from M&S for my own pleasure and ran back to Matt's flat. Running up the stairs and knocking on his door out of breath to have Matt open the door standing naked with his beautiful hard cock sticking out in front of him and pointing directly at me, pushing by him I felt his hard cock brush against the side of my leg as he shut the door and I knew I was in for some fun.Matt told me to strip as he took the back pack from me and emptied the contents on to the sofa picking out a white satin chemise and matching knickers for me and a black satin set for himself before handing me the set he had chosen for me and sitting down telling me to get dressed up as he watched stroking his cock gently, now this made me pause in shock until Matt told me in a firm voice to put the items he had handed me on or he would punish me.So I did as I was told and put first one leg then the other through the leg holes and began hurriedly pulling them up before Matt told me to stop take them off and then dress again slowly so he could enjoy me dressing up, this I did turning around so he could see me pull the satin material over my bum stroking it and then turning to him again and grasping my hard cock and stuffing it in the knickers and adjusting my balls so they were also inside the knickers before again stroking myself through the satin knickers. Slowly putting my arms through the delicate shoulder straps and pulling the chemise over my head then running my hands all over the satin smoothing it over my body, Matt told me to stop and turn around facing away from him with my hands at my side, I began to get nervous until I heard him stand up and felt his hands begin to roam over my satin covered back and bum and then he got even closer thrusting his rock hard cock between my bum cheeks rubbing it all over the satin and encircling me with his arms pinning my arms to my sides as he fondled my cock with one hand and played with a nipple with the other kissing and gently biting my neck before taking a step back telling me to again face him. This I did and watched silently as he picked up the black knickers before handing them to me telling me I had to get him dressed.This confused me a little, how was I going to manage that? “Hurry up or I will put you over my knee and slap your arse” Matt said and I still stood there confused so Matt sat back down and ordered me to come over to him before grabbing my hand that was holding the knickers and pulling me over his knee both fondling and slapping my arse in turn, it was such a turn on I began to grind my hard cock into his leg and moved my side against his cock with each slap he gave me until he stopped and again told me I had to dress him before giving me the knickers as I stood up. I still did not know how I should go about dressing Matt so he told me to get on my knees holding the knickers open for him.This I did and watched as he placed his feet into the knickers one at a time before I began to pull them up over his bum with my face and lips only inches from his delicious cock that I just could not resist as I began to suck and lick it before Matt could stop me, Matt took a step back reaching down for the black satin chemise that he then threw at me and I caught before repeating yet again that I had to get him dressed or he was going to punish me when I had finished. Now I was beginning to understand and enjoy this new game so taking the chemise I stood up walked around him and lifting the black satin chemise with Matt putting his outstretched arms through the shoulder straps letting it fall until it was over his head as well I then smoothed the satin over his body before turning him around and putting his cock inside the knickers whilst staring into his lovely ice blue eyes my hand reaching for his satin covered cock that was rock hard.Matt then pulled me over to the couch again and sat down and pulled me over his knees and began to slowly slap my arse as I wiggled rubbing my hard satin covered cock into his leg until he had to stop or shoot his load, if that was his idea of punishment then I was very happy to be punished like that whenever Matt wanted.We both stood up and his arm encircled my waist pulling me close as we began to kiss Matt yet again began to fondle my arse as I did the same to his arse and we ground our cocks together in a slow sensuous dance until I thought I would shoot my load in my knickers so pulling away slightly but still kissing I put my hand down the waist band of his knickers grasping his cock and pushed it downwards whilst lifting up the lace of the leg hole until his cock stood outside of his knickers before doing the same to my own cock but the opposite side, as I was doing this Matt stopped kissing me not understanding what I had in mind, but after grabbing his cock and gently leading him to the bedroom by it I got onto the bed pulling him after me and laying him on his side facing me I told Matt that I wanted his cock to go up the leg hole of my knickers whilst my cock went into his knickers in the same way but the other side in his.Lying together like that it was as if we had became one from our feet and legs that were intertwined around each other to our cocks wrapped in the others knickers but in contact with each others balls and groin area going all the way to our upper bodies pressed together as our tongues explored each others mouths and our hands roamed over the others bodies so that every time we moved even slightly waves of pleasure rippled through our bodies, it was an exquisite almost torture like feeling because neither of us could move very much because of the way we were intertwined so that the inevitable orgasm was delayed. Even though both of us wanted the orgasm neither of us wanted to cum first delaying it even more until we were both moaning and whimpering in between kissing and licking each others faces, eye lids and necks before returning to deep kissing whilst our hands and fingers sought out and explored the others satin covered bodies touching each others nipples, sides, backs, neck, hair shoulders and arse with one hand whilst both of us finger fucked each other. I could not control myself any longer and my whole body began to shake just before my cock started to throb and shoot out streams of spunk into Matt's knickers as I buried my face into his neck biting kissing and moaning I could feel his cock do the same shooting his warm spunk against my body as we continued to move against and cling to each other until we were both finished and just lying still tight up against each other no longer moving anything other than our hands that continued to gently stroke each other as our breathing and hearts began to go back to a more normal speed.