My first & earliest sexual experiences with a man

My earliest sexual experiences with a man and the first time I was fucked by one. Was with a guy called Dave. I used to meet many years ago, while I was still at school. He was one of my paper-round deliveries. He used to make me to dress as a school girl and wear lingerie. While I sucked him and was fucked by him. He would spank me (not enough to leave lasting marks) and verbally abuse me, while i was sucking him and he was fucking me. He would call me a sissyboi, sissy slut, cock whore, faggot, bitch etc and he made me call him daddy whenever we were alone together (this I found weird at first but then I discovered it made me really horny).

He would make me suck his very large cock (it was approximately the size of a standard can of shaving gel) till he got hard before he fucked me and again after he had fucked me bareback and had cum deep in my ass, which he called my sissy pussy. All this started because he caught me wanking over a page 3 girl in the newspaper one morning. He told me that he would report me to my employer, if I didn't go round that evening and help him with some work in the garden. All this was a pretence on his part.

Just to get his cock in me. It started with a beer, a bit of weed, straight porn videos and magazines that quickly moved to bisexual and gay porn, with us wanking each other, the next thing I knew we were sucking each other off (he actually gave me my first ever handjob and blowjob). This then led to him fucking me and even though he was a top he always made me cum in one way or another. The first time Dave fucked me it hurt like hell. It left me bruised and sore for around a week and occasionally bleeding for a few days (this i had to hide from my parents and school). It was a good thing i only wore black boxer shorts.

This is what happened the first time Dave fucked me. I was already staying the night at his place under the pretence of a sleepover at a school friends house, to study. We were in his bedroom on the bed in a 69 position and i had been sucking his big cock while a porn video was playing. After i had stopped sucking him because he told me to. Dave asked me if i'd ever had my boipussy (this was the first time he had called it something other than my ass) eaten. I replied no, he told me to lie face down on the bed with a pillow under my cock and balls to raise me up and make it easier for him to eat me out.

He climbed up behind me, spread my cheeks and proceded to lick, nibble, suck and probe me with his tongue (i had already showered earlier and shaved my pubes and ass smooth at his request) as he stretched me open slightly. He then told me to hold my cheeks open as far as i could while he continued to eat me out and play with my cock a bit (which he started to call my clitty I thought was a bit weird).Dave suddenly stopped eating me out and i felt something bigger probing at my hole .I tried to say no and get him to stop. Dave growled at me i'll do to you what i want, when i want and held me down and slowly forced his massive cock into me while i screamed and tried to fight him off. Dave told me with a menacing tone, that he loved it when i struggled.

I soon gave up struggling as i had run out of energy and i laid there crying while he raped me . As he fucked me he started to calm down and tell me what a beautiful tight sissy pussy i had and how nice it was. As i laid there sobbing he started to get angry again and shouted at me to stop crying or he'd really give me something to cry about. Unfortunately for me my body betrayed me and cum started to run out of my cock as his cock rubbed my prostate while he fucked me. All of a sudden he stopped fucking me, pulled out and started to laugh as he'd noticed i was cumming. He said look at that my little sissy bitch loves it when daddy fucks her.

I replied you did'nt fuck me you raped me, with that he grabbed me and slapped me round the face and told it was'nt rape as i was enjoying. My body proved that by cumming. Before i could argue he grabbed my head, forced my mouth open with his hands and shoved his semi hard cock in my mouth and told me to make him hard again because he was going to fuck my sweet little sissy pussy some more. When i had got him hard he told me i can cooperate or i can be forced again. Either way he was going to fuck me whether i enjoyed it or not. I politely asked him to be gentle and told him i would cooperate.

His whole attitude changed instantly. He told me to lie on my front and hold myself open as he applied some cold lube to my hole .When he was ready he slowly pushed his cock back in as i winced and started to cry with the discomfort. Dave started to speak softly and gently to me telling me to breath through it and try to push him out like i was going to the toilet. After he had fucked me again for a while with various speed, depth and force, he stopped with his cock pulsating balls deep in me as he flooded my wrecked, bruised and battered ass with his cum. After he had finished cumming he told me clean his cock with my mouth.

I did this without complaint as i was too knackered to argue and to scared at what would happen if i said no. Later on he took me back to the bathroom, showered and shaved the rest of my body while being extremely gentle and nice. Dave told me to go and take a nap and he would wake me in a while. Dave came up and woke me. He told me clothes were in the guest room. I went into the guest room to find a pair of skimpy black lace panties, bra, suspender belt and stockings laid out on the bed and no sign of my male clothes.

I was in shock and a state of panic. I angrily shouted at Dave "where the fuck are my clothes" he came charging upstairs wearing a bathrobe and grabbed me by the throat and slammed me against the wall. He said to me put the lingerie on or the nice treatment will stop and he'll go back to fucking me like the first time earlier today. He left the room and i put the lingerie on, he returned with a girls school uniform and told me to put it on and come down stairs. When i arrived downstairs Dave handed me a large glass of red wine, i gulped it down quickly. He then started to cuddle me and started to kiss me, responded and he started to slide his hand up the skirt and grope my ass through the panties.

He then told me to get on my knees and suck his cock. I slowly dropped to my knees and undid the robe, his massive soft cock was right at mouth height. I started to suck his cock and as it grew in my mouth he moaned with pleasure. I thought to my self if i can make him cum, he won't fuck me. Suddenly he told me to stop or he was going to cum, i disobeyed him and he grabbed my hair and pulled out of my mouth .He made me stand up, slapped me round the face for disobeying him and then bent me over the table, pushed up the skirt and ripped the panties to one side, spat on my sissyboipussy and forcefully slid his hard cock balls deep in me.

I screamed with pain as he did'nt stop till he was balls deep. He told me to shut up and take it you sissy whore, as i cried out in pain with tears streaming down my face, the pain slowly became pleasure as my already ruined sissyboipussy stretched to accommodate his large cock, he continued to fuck me until he was ready to cum then he pulled out and stuffed his cock in my mouth and unloaded into my throat as he throat fucked till he came. I then made me strip down to just the lingerie and go up to his bedroom. Where he continued to fuck my sissypussy (as he called it) and mouth a number of times in various positions.

Till the early hours while verbally and physically abusing me, this included twisting, pinching, pulling and slapping my nipples, cock and balls with varying degrees of force. All the while making me call him daddy and thanking him for it. I finally could'nt take much more and i passed out with exhaustion. When i awoke later in the morning, i was still wearing the remains of the lingerie and parts of me were covered in a mixture dried cum (some of it mine), anal juices, spit and lube. My nipples were bruised, my balls ached, my cock was sore and bruised in places.

My asshole was bruised, battered and loose enough that i could slide my fingers in with minimal resistance. It was oozing a mixture of cum (some of it my own as Dave had decided to use my own cum as lube when i came while he was fucking me), lube, a small amout of blood, anal secretions and spit. Dave came into the room looking and acting like a totally different person. He could'nt of been nicer. He told me to have a shower, put my male clothes and have some breakfast. Later he drove me back to not far from my parents house, as he dropped me off he said see you next weekend Chrissi and told me i better not tell anyone about what happened as nobody would believe me anyway.

For most of the next week my whole body ached, my nipples, cock and balls were bruised and sore. My asshole slowly recovered but was bruised, occasionally bleeding (this i had to hide from my parents and school). It was a good thing i only wore black boxer shorts. I managed to avoid Dave for most of the week when i delivered his papers, but little did i realize that he knew my parents and when i got home from school my mother told me Dave had phoned and asked if i'd like to earn some extra cash over the weekend. Helping him in the garden and with stuff to the house. She told me she'd already agreed and he would be picking me up at 5pm friday. When friday came i was a nervous wreck inside, Dave picked me up.

The first thing he said was. Bet you were surprised when you found out i knew your parents. I replied yes daddy (as i did'nt want to anger him). When we arrived at his house and went in, he kissed me and pushed me down to my knees, i knew what he wanted. Undid his trousers and took his cock out .I proceeded to make him hard and without warning he grabbed my head and unloaded a massive load of cum in my mouth, which i swallowed without hesitation. He told me i was a good sissy and told me to go and get ready.

I asked him if he could be a bit gentler with me this time as i'd had a hard job explaining some of he bruises and discomfort i'd been in. He told me it would all depend on how i behaved. As he escorted me to the bathroom he said firstly i'm going to give you a enema so that you will be nice and clean wont make me angry by making a mess. During the enema procedure which took around a couple of hours, he had me repeatedly suck his cock, but he did'nt cum ( i later found out his sexual stamina was down to viagra).

After the enema was complete he told me to shower and shave my body. While i was final rinsing he stepped in the shower with me. His cock was rock hard and throbbing, he grabbed a handful of vaseline smothered his cock with it and turned me to face the wall, as he spread my legs and bent me slightly forward. I felt his cock slowly enter me. It hurt like hell but with a bit of breathing and hiding the fact i was in pain he carried on slowly fucking me until he unloaded his cum deep in my guts. He pulled out, left me in the shower with instructions to finish up and get dressed with the clothes in the guest room.

This time there was, white thigh high hold up stockings, g-string, bra, a leather collar with three chains with clips on the ends attached, a strange looking rubber thing and strange looking thing made of shiny metal that looked like a small dog muzzle (i later found out was a butt plug and a chastity cage). got dressed in the lingerie, but did'nt know what to do with the other item. So i took them down stairs to Dave hoping he would'nt be angry. Surprisingly he was'nt. He told me to lower the bra as he fastened the collar around my neck, i felt two sharp pains as he attached two of the clip to my nipples and he put the bra back into position. He then told me lower proceeded to lock my cock and balls in the chastity cage, While telling me my clitty was out of bounds for me to touch except for when i cleaned through the cage after going to the toilet.

He then hooked the third chain to the chastity cage , i went to pull up the g-string, he stopped me and told me to get on my knees. I instinctively dropped and opened my mouth. Dave laughed, held up the butt plug and said this isn't going in there, now put your forehead on the floor and show me your sissypussy. I knelt forward and pulled my cheeks apart. I felt something cold on my hole and a something push at it, i thought he was starting to fuck me. So i stayed still, then my hole opened and i felt a sharp pain and something larger than i'd felt before go I and stop. It felt weird .

Dave told me to stand up and pull up the g-string , i timidly asked what the thing was that he'd put in me. I got told it's a plug Chrissi to train your pussy to stop you crying every time i fuck you. With that he attached a lead to the ring connecting the three chains and gave it a sharp tug, i whimpered ,but my caged cock betrayed me by twitching and leaking a small drop of cum, mainly thanks to the pressure from the plug and my clenching on it as my nipples were tweaked. Dave commented, looks like the little sissy slut likes it, as he slapped my ass hard a few times. At every slap i whimpered, clenched and dripped more cum.

Fast forward a few hours during which time. My nipples had been tweaked a number of times causing after effects and the plug had been removed and reinserted a number of times, leaving me a gaping, quivering mess and the g-string soaked with cum, due to Dave discovering what this did to me. Later on Dave decided it was time for him to fuck me. He led me up to the bedroom with the lead. I assumed the usual position on my knees with my mouth open, without being asked.Dave told me to stand up and led me over to the bed, where he laid on his back and told me to make him hard, when he was read.

I was told to stand up, take the g-string off and bend over the bed. Without warning the plug was removed and he buried his cock balls deep in me, as i groaned with a mixture of pain, pleasure and surprise (more pleasure than pain as i was starting to enjoy the treatment) he stuffed the cum soaked g-string into my mouth. As he fucked me with a mixture of his cock and the plug, he pulled on the clamp chain. I went weak at the knees and experienced such a powerful orgasm i temporarily blacked out. When i came around i was on my back with my feet over his shoulders as he pounded my gaping slack hole.

With a final hard deep thrust, he stopped balls deep in me and i could feel his cock twitching as he unloaded deep inside me. He told me i was a good little sissy. After i had cleaned his cock and got him hard again and swallowed his load, he removed all the devices and the lingerie. Took me to the bathroom and helped me shower due to my legs being wobbly. He fed me and got me slightly drunk and i went to bed in the guest room because he stated that if i got back in his bed. He would'nt be able to control himself and i had to go home the next day. In the morning i gave him a last blowjob before he took me home.

I continued to go round to his house and see him as often as possible. Sometimes even bunking off school, to spend the day with him. As i was addicted to what and how he made feel. Then one day, the paper delivery was cancelled and he had moved away while I was on holiday. I was around 16½. I later found out that he was a divorced father and the various items of female clothes including most of the lingerie (but not all of it,some of it he bought specially to fuck me in) and school uniform he got me to wear when we were together were his daughters who left them there while she was away at university. So many happy memories, some of them were painful at first when the experiences that made them happened, but now when i remember them i get highly aroused.