Karl and Sonia at Last
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Karl Blossoms Into Kim free porn video
I run an Engineering Consulting Firm, small operation, just me and a few assistants. One is an intern , Karl, he attends college at night and interns for a few dollars, just to gain some experience. Now before I go further, let me describe Karl a little. Karl is about 19, thin and he has believe it or not some rather shall we say delicate features. For instance, he has hardly any facial hair, he is a little soft spoken and shy and he has hair down to almost his chest.
Now I must confess, I am a bit of a pervert and yes I have fantasized about screwing him, though as I said he is thin, he does have a round prominent ass and from the rear, his ass combined with the raven black long hair make him look so much like a girl. In fact on several occasions, clients who never met him, mistakenly addressed him as Miss when his back was facing them. Of course they apologized when he turned around, but you get the idea.
Last Tuesday Karl asked to speak with me. Karl told me he was in dire straits, He needed to earn some real money as his mom had to stop working due to illness. A position for receptionist was open, but I told him I only hire young attractive girls for receptionists, no offense it's just my business practice and in my experience young attractive ladies make for the best receptionist. Karl begged me to reconsider and after a few minutes of his begging, a filthy idea popped into my mind.
I told Karl, that if he would stop by my flat early Friday evening, we can talk it over and if he could convince me, I would give him a try. I warned him that he would have to carry himself in a way he is not used to if he were to be a receptionist for me. Karl inquired as to what I meant and I assured him all would become clear Friday. I decided I was finally going to have sex with him and that I could easily seduce him or even be a little forceful if need be, but I will get to have him. I felt a little dirty and slimy that I would take advantage of this k** in dire straits, but lust got the best of me.
Thursday night I visited the lingerie shop and picked up a few "surprises" for Karl, you will hear about these later. Friday 6pm there is a gentle knock at my door "Mike, it's me, Karl" I had to contain myself and not rush to greet him, though I felt blood beginning to rush to my cock. I answered the door and welcomed Karl in. I asked if he had eaten yet and he said yes, "Great Karl, would you like some wine?" Karl said yes and we both drank, but I made sure Karl got most of it. When I was sure Karl was relaxed, I told him that I smoke weed from time to time and had just gotten hold of some really powerful stuff would he like to try it with me?
Karl looked a little shocked, that someone my age smoked, but he eagerly said yes. "Okay Karl, let's have a small bit of weed then we will discuss that receptionist spot, BTW I think it can work out for us both. Karl and I smoked the weed, but I only faked taking deep drags and made sure he got a good amount.
Now it's August, Karl is dressed in short denim shorts , sandals and a sleeveless t-shirt. I notice he has very light body hair, more like fuzz than actual hair. I sat closer to him on the couch then spoke "Karl you know for a young man you really keep your hair so well groomed. I know it's hard because I had similar hair when I was your age, wow yours looks great, so healthy" Karl blushed a bit but I knew I was making progress.
"Karl just for conversation, how bad do you really want that job? You know how I feel about giving it to only a woman." Karl responded simply with "I will do anything to get that job" I laughed and replied "Karl, what am I always telling you as an Engineer, Never say you would do anything right?" Karl nodded and repeated anything. I got closer to him and said "are you serious Karl?" He said nothing, now I felt I would risk it, I would make my move. "Karl, remember when that client thought you were a girl from behind, God I laughed so hard, you know Karl you do have hair and a figure that can be mistaken for a girl, certainly from behind". Now I sensed Karl was getting very uncomfortable, so I went "for broke". I stoked Karl's smooth thigh and said "So you really mean anything" Karl got up immediately and yelled "You pig, are you serious, keep your filthy hands off me, I am leaving now!"
"Ok Karl you can leave, but forget your internship, forget your letters of recommendation and certainly forget earning any money with me ever again." I then got up and grabbed Karl by his arms, "Listen you brat you said anything right? so now you made my cock hard and you think your walking out? think again faggot" Karl struggled to break free but I got rougher, and wrestled hard with him, as I did I told him it is futile to resist, I told him I would stop if he promised not to leave. "Come on Karl, let me try to explain a few things honestly, remember, walk out that door and your career is finished"
Karl, still angry did sit down. "Karl, have you not ever had certain thoughts about different parts of your body, related to sex?" "Let me be blunt, tell the truth, have you ever experimented and played with your anus when masturbating?" "Mike you are sick" "That may well be Karl, but be honest answer my question" "OK yes, once or twice but that was many years ago, I was only 14" "That is OK Karl, what is important is, did it feel good, did you like it?" Karl relaxed some the weed and wine peaking now. "Yes I admit I came very hard, yes I enjoyed it" "Did you continue to do it Karl?" "Maybe 2 or 3 more times but then I stopped, I felt dirty and I felt like a fag" "Karl, that is so silly, why did you deny yourself such intense orgasms because of what others may think, I mean how stupid, how would anyone know you even did it?"
"Now Karl I appreciate your honesty, one other question, have you ever wore a girls underwear like panties or stockings?" "FUCK YOU MIKE, you are so sick" "Karl please just say yes or no, I am trying to make a point here" "Fuck you, yes I tried my mom's silk panties and stockings once and ONLY ONCE" "Karl did you masturbate when you wore them, don't lie, I know you had to" "Yes , I felt so turned on by the feel of the silk and the nylon, truth be told, I never came like that before, I completely made a mess I came so much, BUT I never did it again, after I came I felt so disgusting, I mean I felt like I was becoming a queer so I got scared and stopped"
Now I moved closer again. "So Karl, you denied yourself such extreme pleasure, because of an irrational fear, don't you see no harm was done, don't you understand no one would have to know, what is a man anyway, does a man let the majority decide for him how he should have harmless pleasure??"
"Okay Karl, you have been very honest with me, so I will be honest with you, you can have the job and I'll even pay you 15% more than what is posted, if you will oblige me and tonight rediscover and wake up those feelings of extreme pleasure you once had at 14"
Karl surrendered, "Mike what do you want" "Karl, I will not force you to do anything the choice is yours, but I would like to see you wear something I brought for tonight". I went to the closet and got a pair of very silky and shiny nylons and a black tiny thong. "Here Karl get into these, see if you feel good in them, see if it brings back good memories"
Karl froze, I knew he was wrestling in his mind, I knew from his eyes he wanted to feel those intense feelings again but he was struggling with the guilt of becoming a fem boy.
"Her Karl let me help you, I very gently placed my hands on Karl's pelvis and helped him undo his denims, then I removed his shirt, finally Karl stepped out of his briefs. My God he has only peach fuzz, he looks so smooth. I helped him hold his balance while he stepped into the thong, his cock shrunken with shame and fear. Then I had him sit down and watched as he put on the nylons. When done I sat next to him I spoke very softly and soothingly to him. "Karl, relax open your senses, concentrate on how those nylons feel"
I took his hand and gently used his hand to slowly stroke his nylon clad thigh. Karl resisted at first but I persisted, then it happened, his tiny shrunken cock grew into a throbbing monster, he picked his ass of the couch and ripped off the thong that was strangling his engorged cock and now tight ball sack. "See Karl, don't fight it, look at your cock, your as big as a horse, you know it feels good Karl, judging by your cock I would say you love it"
"Karl, lets smoke some more weed, shall we?" We did, and Karl was completely relaxed now. I pulled his soft naked body into my lap and stroked his thighs and played with his hair. "Karl, I have good news, the job is yours, what happens next I leave up to you, but you earned the job" I took a big gamble, but I just knew Karl wanted to go further, he just needed encouragement. I slowly groped his young smooth body, his ass as round and soft as any woman's. Then I said nothing, but got up and got undressed. Karl did not mind, I had him stand and continued to feel and grope him and he just surrendered to his passions.
9 days ago
"Karl I am so happy you stayed, now what about the other thing you did at 14 you know fiddling with your bum" Karl just nodded that he understood. "Karl your cock is throbbing, would you like me to gently play with your bum, let's see if you still like it?"
Karl said nothing, I went behind him still standing and slowly pulled him to me by holding and rubbing his breast, then I slowly but forcefully rubbed my throbbing cock along his ass crack. I whispered to him and told him how nice it felt. "Karl, can I rub my cock head near your bum, I promise nothing more, than just rub and gently press your anus" Karl spoke "Yes I think I would like it" I told Karl to wait, I hurried back with some lube and lubed his ass crack and both cheeks, then I went back to placing my cock in his ass crack this time pressing my cockhead against his anus, not trying to penetrate but just holding my cock parallel to his crack with my head against his bum.
Karl let go, he let himself free, I had to see what he felt, I reached and felt his cock, he was already leaking a tiny pre-cum drop. "WHOOA Karl, slow down, lets both enjoy the moment, go sit down now and take a breather" Karl sat at the edge of the couch, I approached and ran my fingers through his hair, "Karl let me be honest, I thought about this a long time, you turned me on a long time ago, The job was yours the moment you told me about your mom, I just apologize for making you think you needed to do this, you did not, but now you see you do enjoy it, so lets relax and enjoy each others body OK?"
Karl smiled and nodded yes. I held my cock and started moaning and humming while I stroked Karl's thighs. "Karl you have been so honest about your younger years, so tell me have you ever played with or even tasted your own cum?" Karl responded "No honestly Mike I have not but I did think about it and I did wonder what it would be like"
I gently stroked his body while stroking my cock, I knew he liked the feel of me touching him, I continued until he leaked a small pearl of pre-cum. Laughingly I said "Well Karl, here is your chance, you just leaked a nice little pearl, why not go for it?" Karl very slowly was struggling with the thought, he wiped his pre-cum onto his finger and finally brought it to his lips....
Next I told Karl to use the leather couch and take his favorite position he uses when he masturbates. Karl lied on the couch on all fours. I got my black t-shirt and laid it down on the couch. Karl knew what I wanted and started finger his ass. I touched him all over and he just moaned with pleasure as I touched him. I rubbed and kissed his sweet ass. I felt his smooth chest and spent a while stroking his thighs.
Karl, you seem to like being touched by a man, "Yes Mike, I never had a man touch me like you are, but I have thought about it when I wore my mom's stockings." "Karl let yourself go, imagine you are a girl, in fact I WILL FROM NOW ON CALL by a girls name when we are alone is that OK with you?" "Yea Mike I'm up for that Hmmm OK CALL ME KIMBERLY OR KIM I like that name"
"I like it also Kim, now we will go further, please cum for me, I will help you, but be a girl, make believe your cock is a girls clit, call it your clit, if you do I just may touch it, because after all you will be a girl and I would be touching a clit not a cock"
Kim now sat on the edge of the couch, and open his legs wide, he started wanking and he closed his eyes as his pleasure grew. All the while, I touched and felt him all over, he especially loved when I stroked and felt his smooth girl like thighs.
"Kim, don't be scared, but I am going to up this a bit" Kim just kept wanking and managed to moan out with "please do". I sad nothing, I got between Kim's legs leaned forward and forced my tongue into his mouth. He reflexively pulled back. I then grabbed him by the sides of his head, his hair brushing on the back of my hands and pushed him back preventing him from being able to move. I once more kissed him, after a few seconds, he surrendered , in fact he enjoyed being kissed and his tongue caressed mine. He went back to wanking and I back to groping. "Go ahead Kim, let your self just go "
With that I started getting very aggressive with my groping and stroking, He was starting show all the signs of nearing his climax, I kissed him once more and placed my hand on his and used it to wank him. He stopped the kiss and loudly said "Oh God Oh shit I'm goanna cum, I kept my hand on his but moved back as I of course wanted to watch. I let him go and quickly got the black shirt on the floor.
His climax started, his strings of cum were violent and large, his whole body got into it and he thrust his hips with each squirt of cum. "Good girl Kim, cum as much as you can for me, show me how much you like this and like me being your man"
Kim, just kept launching long violent streams of "her" pearly white creamy cum" Eventually his ejaculations died off and she caught her breath, the level.
Kim returned today about noon, she immediately kissed me and stripped. I told her to go get "dressed" in her stockings I gave her. We both were naked and sitting on the couch. I surprised Kim with some opiate hashish, he never smoked it before only ordinary weed.
Kim lets relax, try this, I know it makes me very horney and I am convinced it will do the same for you. We passed the small pipe back and forth and lit the hashish for each other.
I smoked far less than Kim, sneaky me, I wanted full control of her and the advantage of her being fully under the influence of the d**g.
Kim's reaction to the d**g was ideal, she felt mellow and dreamy BUT was very lucid and spoke as if she were sober. Kim said it was more a "body high for her, she said she felt euphoric and yes horney but not stoned. We began talking. "Kim remember yesterday when you tasted your pre-cum? You told me then you were intrigued and liked it some" Today let's advance, lets take a very large step only if you feel your ready"
"Mike, don't go on any further, I know where you are going, I am willing and even turned on by the idea but I am scared it is a point of no return, in other words if I do it, I can never be the same again" I talked to Kim, very calmly and encouraged her, I told her nothing is permanent, she is wrong she can always "go back" and just think of this as an experiment, kind of like young teens experiment with d**gs.
Kim said nothing other than to tell me to please stand as she moved and sat at the edge of the couch. I gently approached her with my throbbing cock, she just stared, I knew she was struggling with the idea but down deep she wanted to try it. Finally she pulled me to her by my ass, and placed her mouth on the head of my engorged cock. She froze for a few seconds, than as if she was experienced, which I knew she was not, she reflexively stroked and teased my cock head with her tongue. Finally she slowly took the throbbing hot shaft completely in her mouth. She did this very slowly and several times I had to teach her to be cautious with her teeth..............
Kim really listened well, she really wanted to learn. I then taught her about various ways to use her tongue and that she should use her hands to gently caress a mans ball sack and also stroke his ass or thighs.
Now since I am teaching Kim, I am really not approaching any sort of climax as my mind is occupied with teaching her and I really cannot concentrate on the actual pleasure.
"Kim, I think you learned quite a few things and I think you learned them well"
"Mike remember, I do watch porn and I just imagined what I would like if a woman were sucking me, so it was just a matter of putting all together"
"Good Kim , very good. Lets talk some and lets smoke just a little more than I will let you show me what you can do without any coaching from me, OH and BTW don't be afraid or anxious, I will leave it up to you whether or not I cum in your mouth. I realize that is a very big step, so Kim let me be clear, I will give you ample warning when I am about to cum and then you decide where you want my seed to end up. Also realize I feel it will be a large load so bear that in mind OK?"
Okay Mike I understand, I promise you I will use everything you taught me, Can I wank myself while I do you?"
"Kim don't be silly of course you can wank, I want you to have pleasure also, just as much as any woman I have sex with. I always make sure my partner get's her desires filled and orgasms"
We smoked some of the opiated hash, and then I spoke very gently and lovingly to Kim while I stroked her lovely hair and groped her smooth soft body.
"Mike, you woke something up in me, I never felt this way before other than when I wore my mom's stockings and panties, but this is 100 times more intense"
"So Kim I guess you are enjoying becoming a woman, am I right??"
"Yes you are, Mike I want to suck you now, please do not coach me, please just concentrate on the pleasure I hope to give you, only interrupt me if I do something wrong OK Mike?
" Yes my love, just do not forget, you choose where I cum"
Kim said nothing more she sat on the edge of the couch and asked me to stand. I did and she began to suck me. My God she was so into it, her tongue actually vibrating as she hummed and pressed it along the bottom of my cock, she did this while stroking her head for and aft along my throbbing cock. I held her face in my hands gently and just was in heaven as I felt her full silky long hair brush my hands and sometimes my thighs.
Kim would wank herself on and off, She stopped wanking and all of a sudden pulled me by mass and forcefully had my cock impale her moist warm mouth so deep that her lips pressed against my balls. Now she wanked herself non-stop. I opened my legs wide to make sure she had room enough to pleasure herself. She tickled the bottom of my cock-head with her tongue as she wanked furiously, then she went back to taking me as deep as possible once more. I felt her lips vibrate against my ball sack.
I was groping Kim's shoulders and thighs when I felt her body start to spasm, she was cumming and I could tell she was ejaculating a very large load as I felt some of her juice strike my knee and lower thigh. Also the spicy scent of her cum was so intense and her spasms lasted so long I had to look.
God her thighs and pelvis were drenched with her pearly juice. the sight of which brought me to climax, I held back and loudly screamed my warning to her. "Kim I can't hold out I going to cum right now" I was certain Kim would remove my cock and wank it to orgasm BUT NO, she just went wild and sucked me and tongued me.
My whole body trembled as I unloaded into her mouth, violent ropes of cum they were. All the more violent as they were sucked strongly as I shot, Kim immediately but gently squeezed my balls as if to milk my seed. Funny, she accepted my every rope but did not swallow, but rather just let my cum flood and eventually start to spill and flow down her chin and neck. I felt my balls become wet with my own cum. Kim milked every drop of my massive load. Finally I had to force her to stop. She did but kept me in her mouth as I deflated a bit. I realized now why she did not swallow, she was savoring the taste of my cum. Eventually she emptied her moth and just let my cum flow all over her chest and chin while she closed her eyes and rubbed it in like some sort of lotion.
"God Michael, you taste so sweet, I did not want to swallow, I wanted the taste to last, then I wanted your sweet creamy cum, I wanted to feel it on my hands and skin"
Kim told me she was certain she would not have had me blast in her mouth, but she tasted a drop of precum and decided right then she loved it.
Kim went on, "Michael your cum was fucking hot, I mean really warm, I loved it!!
"Kim lets shower, then I want to talk to you." We showered together, I kept playing with Kim's ass during the shower, even grinding my cock into the crack of ass cheeks.
"Kim, I want you to go home like yesterday get a nice long sleep, i'll give you some of the hash to help get drowsy if you like.
Now I guess you know what I would like us to do tomorrow yes?
"Yep Mike, I do and I want to experience it, BTW I already read all about it yesterday before bed. Don't worry I know all about the enema and douche, I'll be nice and fresh for you"
"Kim, you learned about anal ?? wow "
"I told you Michael, you awoke something in me and I want to experience it all"
Next day Kim arrived as usual a little past noon. She went straight to my bedroom and asked me to give her a few minutes alone. Finally she called me, God was I astounded, she was naked except for stockings and woman's high boots but the astounding part was she had applied some makeup to her eyes and a deep red lipstick. Nervously she asked how she looked. I did not answer but instead tore my cloths off as my cock sprang like spring. I grabbed her all over and groped her.
"Kim lets go slow, unlike yesterday, this you have to get used to and most of all be as relaxed as possible" I then laid on my back on the bed and instructed Kim to mount me in the 69 position with her boi-pussy in my face. I told her not to make me cum if she decided to play or suck, but I am doing this for a reason. Kim obeyed and I am now tonguing her anus. She is cooing with delight and slowly strokes my cock and also sucks on it every now and then. "OK Kim now get ready to relax your "pussy" as much as you can" I waited for a few seconds then I lubed my finger with KY jelly that I had taken to the bedroom with me. I then very gently and slowly invaded her with my finger. Kim let a sound that was part pain but also part pleasure I stopped when I was in her deep and we just remained motionless. "Kim, I want you to fuck my finger, make believe it is a cock and you are going to use your pussy to fuck it.
Kim said nothing, but she immediately started gyrating on my finger. She instinctively squeezed it tight with her anus muscles and it felt as if she were sucking my finger into herself. I also felt her cock throbbing my lower chest. "OK Kim, now just relax, I want you to feel something new and I promise it will not hurt any more than you feel now.
I found Kim's prostate after a few seconds and oh so gently massaged it. Kim was ecstatic and asked what I was doing, Kim said she felt like she would cum "Don't worry I would not be upset at all if you came, I would understand, but please do your best to not cum and wait for later. "Mike, OK, please continue doing that and I promise I will tell you to stop when I am close to cuming "
I then explained what I was doing, I explained about her prostate and how she will feel even more pleasure when my cock-head and shaft press on it later. I then explained edging to her, but Kim told me she does that all the time masturbating but she did not know it was called edging. We both kept at the massage while I kissed and tongued her ass cheeks.
"Mike I am relaxed, I can not wait anymore, let's do the "real thing"
"Good Kim, here is what we will do, this is your first time so, I will remain here on my back, I want you to squat over me , facing me, and lower yourself as slow as you need onto my cock, I will help guide you. I want to do this because it will give you complete control of every aspect. In fact it will be you who fucks me , you will control the depth, the force and rhythm all to your liking"
"Oh God that sounds so great, give that jelly let me use it and get my self nice and slippery" After Kim applied a very large dollop of the KY to her pussy, she lubed my cock and I almost came.
Kim now did everything as instructed. she held my cock with one hand and squated. She had perfect aim and I felt my cock head bear the pressure of her anus. "Ok Kim just go slow , we have all day and all night" Kim lowered herself just enough for my cock head to pierce her, she stopped and made a sound indicating that she was startled and eyes opened wide as saucers. "Kim believe it or not, but it will get easier from this point foreword just take your time. Kim listened and very very slowly lowered herself onto my large hard throbbing cock. She stopped many times and just stayed motionless, adjusting to how it felt. "Kim you are doing exactly what you should be doing, just take your time."
"Mike I don't know if you will understand what I am going to tell you, but I never knew I could feel pain and extreme pleasure at the same time, I love this, I never felt anything like this, honest Michael" Eventually Kim lowered herself completely onto my waiting cock. she stood motionless for a few moments , her eyes closed and she had such a dreamy and ecstasy filled face on her. Then I said nothing, she began to move slightly on my cock. She was amazing she combined sliding up and down with a rotation side to side of her thin hips. Of course she did this very slowly. "Kim open your eyes, I want to look into your eyes I want to see them as you feel more and more pleasure." Kim opened her eyes and her face expressed such ecstasy mixed with surprise. Kim was now feeling hardly any pain, it was all pleasure now. I know because I saw the ecstasy in her eyes and she started fucking me at a nice pace, gradually increasing the cadence. Eventually she would slam hard on her down stroke, moaning and sighing sounds of pleasure. She would slam my pelvis so hard that my balls would vibrate God that felt so good. I held her thighs and pulled her down now as I thrust myself into her. Kim is screaming with pleasure now, then a look of shock comes over her face, she is cumming, no hands cumming, her sperm shooting so fast and way past my head, I swear I heard two or three very violent ejaculations as they hit the bed's head board with tremendous force. Kim is crazy now.
The sight and feel of her cumming was too much. As she ejaculated every one of her violent strings, I felt her anus contract and actually suck my cock. "Kim , fuck me hard now I am going to cum, I am going to fill you!!" Just as I got the last word out I climaxed, I felt my cum shooting deep inside Kim, Kim never slowed down, in fact she sped up and her fucking became wildly forceful. "Mike I feel it, I feel it, I feel your cum shooting very high up into me" I don't know to this day how long I kept shooting large ropes of cum, but after a few seconds, my cum started to squirt out of Kim's pussy on each of her down strokes. Her ass cheeks and my thighs are drowned in a flood of my cum, Kim loved it I looked deep into her soft eyes as my strings started to diminish and finally stop. "Michael I l...) she caught herself I knew what she was about to say but she caught herself and did not finish the statement but her eyes did.
Kim was all woman now, though she swung both ways. I was the only man she would fuck but she did fuck several girlfriends. Kim remained my secret fem-boy for the remainder of her college years. At 23, Kim told me she had met a very kinky girl, when he went on a job interview in another state. "Michael, I know I will get that job, they just about said so, My girl Lois is very kinky, she pegs me sometimes with a really large dildo and also likes to be a dominatrix and I her slave. Michael we are going to marry" Kim just cried her eyes out that she had to move to get that job. We kissed and both understood all good things must eventually end
Now I must confess, I am a bit of a pervert and yes I have fantasized about screwing him, though as I said he is thin, he does have a round prominent ass and from the rear, his ass combined with the raven black long hair make him look so much like a girl. In fact on several occasions, clients who never met him, mistakenly addressed him as Miss when his back was facing them. Of course they apologized when he turned around, but you get the idea.
Last Tuesday Karl asked to speak with me. Karl told me he was in dire straits, He needed to earn some real money as his mom had to stop working due to illness. A position for receptionist was open, but I told him I only hire young attractive girls for receptionists, no offense it's just my business practice and in my experience young attractive ladies make for the best receptionist. Karl begged me to reconsider and after a few minutes of his begging, a filthy idea popped into my mind.
I told Karl, that if he would stop by my flat early Friday evening, we can talk it over and if he could convince me, I would give him a try. I warned him that he would have to carry himself in a way he is not used to if he were to be a receptionist for me. Karl inquired as to what I meant and I assured him all would become clear Friday. I decided I was finally going to have sex with him and that I could easily seduce him or even be a little forceful if need be, but I will get to have him. I felt a little dirty and slimy that I would take advantage of this k** in dire straits, but lust got the best of me.
Thursday night I visited the lingerie shop and picked up a few "surprises" for Karl, you will hear about these later. Friday 6pm there is a gentle knock at my door "Mike, it's me, Karl" I had to contain myself and not rush to greet him, though I felt blood beginning to rush to my cock. I answered the door and welcomed Karl in. I asked if he had eaten yet and he said yes, "Great Karl, would you like some wine?" Karl said yes and we both drank, but I made sure Karl got most of it. When I was sure Karl was relaxed, I told him that I smoke weed from time to time and had just gotten hold of some really powerful stuff would he like to try it with me?
Karl looked a little shocked, that someone my age smoked, but he eagerly said yes. "Okay Karl, let's have a small bit of weed then we will discuss that receptionist spot, BTW I think it can work out for us both. Karl and I smoked the weed, but I only faked taking deep drags and made sure he got a good amount.
Now it's August, Karl is dressed in short denim shorts , sandals and a sleeveless t-shirt. I notice he has very light body hair, more like fuzz than actual hair. I sat closer to him on the couch then spoke "Karl you know for a young man you really keep your hair so well groomed. I know it's hard because I had similar hair when I was your age, wow yours looks great, so healthy" Karl blushed a bit but I knew I was making progress.
"Karl just for conversation, how bad do you really want that job? You know how I feel about giving it to only a woman." Karl responded simply with "I will do anything to get that job" I laughed and replied "Karl, what am I always telling you as an Engineer, Never say you would do anything right?" Karl nodded and repeated anything. I got closer to him and said "are you serious Karl?" He said nothing, now I felt I would risk it, I would make my move. "Karl, remember when that client thought you were a girl from behind, God I laughed so hard, you know Karl you do have hair and a figure that can be mistaken for a girl, certainly from behind". Now I sensed Karl was getting very uncomfortable, so I went "for broke". I stoked Karl's smooth thigh and said "So you really mean anything" Karl got up immediately and yelled "You pig, are you serious, keep your filthy hands off me, I am leaving now!"
"Ok Karl you can leave, but forget your internship, forget your letters of recommendation and certainly forget earning any money with me ever again." I then got up and grabbed Karl by his arms, "Listen you brat you said anything right? so now you made my cock hard and you think your walking out? think again faggot" Karl struggled to break free but I got rougher, and wrestled hard with him, as I did I told him it is futile to resist, I told him I would stop if he promised not to leave. "Come on Karl, let me try to explain a few things honestly, remember, walk out that door and your career is finished"
Karl, still angry did sit down. "Karl, have you not ever had certain thoughts about different parts of your body, related to sex?" "Let me be blunt, tell the truth, have you ever experimented and played with your anus when masturbating?" "Mike you are sick" "That may well be Karl, but be honest answer my question" "OK yes, once or twice but that was many years ago, I was only 14" "That is OK Karl, what is important is, did it feel good, did you like it?" Karl relaxed some the weed and wine peaking now. "Yes I admit I came very hard, yes I enjoyed it" "Did you continue to do it Karl?" "Maybe 2 or 3 more times but then I stopped, I felt dirty and I felt like a fag" "Karl, that is so silly, why did you deny yourself such intense orgasms because of what others may think, I mean how stupid, how would anyone know you even did it?"
"Now Karl I appreciate your honesty, one other question, have you ever wore a girls underwear like panties or stockings?" "FUCK YOU MIKE, you are so sick" "Karl please just say yes or no, I am trying to make a point here" "Fuck you, yes I tried my mom's silk panties and stockings once and ONLY ONCE" "Karl did you masturbate when you wore them, don't lie, I know you had to" "Yes , I felt so turned on by the feel of the silk and the nylon, truth be told, I never came like that before, I completely made a mess I came so much, BUT I never did it again, after I came I felt so disgusting, I mean I felt like I was becoming a queer so I got scared and stopped"
Now I moved closer again. "So Karl, you denied yourself such extreme pleasure, because of an irrational fear, don't you see no harm was done, don't you understand no one would have to know, what is a man anyway, does a man let the majority decide for him how he should have harmless pleasure??"
"Okay Karl, you have been very honest with me, so I will be honest with you, you can have the job and I'll even pay you 15% more than what is posted, if you will oblige me and tonight rediscover and wake up those feelings of extreme pleasure you once had at 14"
Karl surrendered, "Mike what do you want" "Karl, I will not force you to do anything the choice is yours, but I would like to see you wear something I brought for tonight". I went to the closet and got a pair of very silky and shiny nylons and a black tiny thong. "Here Karl get into these, see if you feel good in them, see if it brings back good memories"
Karl froze, I knew he was wrestling in his mind, I knew from his eyes he wanted to feel those intense feelings again but he was struggling with the guilt of becoming a fem boy.
"Her Karl let me help you, I very gently placed my hands on Karl's pelvis and helped him undo his denims, then I removed his shirt, finally Karl stepped out of his briefs. My God he has only peach fuzz, he looks so smooth. I helped him hold his balance while he stepped into the thong, his cock shrunken with shame and fear. Then I had him sit down and watched as he put on the nylons. When done I sat next to him I spoke very softly and soothingly to him. "Karl, relax open your senses, concentrate on how those nylons feel"
I took his hand and gently used his hand to slowly stroke his nylon clad thigh. Karl resisted at first but I persisted, then it happened, his tiny shrunken cock grew into a throbbing monster, he picked his ass of the couch and ripped off the thong that was strangling his engorged cock and now tight ball sack. "See Karl, don't fight it, look at your cock, your as big as a horse, you know it feels good Karl, judging by your cock I would say you love it"
"Karl, lets smoke some more weed, shall we?" We did, and Karl was completely relaxed now. I pulled his soft naked body into my lap and stroked his thighs and played with his hair. "Karl, I have good news, the job is yours, what happens next I leave up to you, but you earned the job" I took a big gamble, but I just knew Karl wanted to go further, he just needed encouragement. I slowly groped his young smooth body, his ass as round and soft as any woman's. Then I said nothing, but got up and got undressed. Karl did not mind, I had him stand and continued to feel and grope him and he just surrendered to his passions.
9 days ago
"Karl I am so happy you stayed, now what about the other thing you did at 14 you know fiddling with your bum" Karl just nodded that he understood. "Karl your cock is throbbing, would you like me to gently play with your bum, let's see if you still like it?"
Karl said nothing, I went behind him still standing and slowly pulled him to me by holding and rubbing his breast, then I slowly but forcefully rubbed my throbbing cock along his ass crack. I whispered to him and told him how nice it felt. "Karl, can I rub my cock head near your bum, I promise nothing more, than just rub and gently press your anus" Karl spoke "Yes I think I would like it" I told Karl to wait, I hurried back with some lube and lubed his ass crack and both cheeks, then I went back to placing my cock in his ass crack this time pressing my cockhead against his anus, not trying to penetrate but just holding my cock parallel to his crack with my head against his bum.
Karl let go, he let himself free, I had to see what he felt, I reached and felt his cock, he was already leaking a tiny pre-cum drop. "WHOOA Karl, slow down, lets both enjoy the moment, go sit down now and take a breather" Karl sat at the edge of the couch, I approached and ran my fingers through his hair, "Karl let me be honest, I thought about this a long time, you turned me on a long time ago, The job was yours the moment you told me about your mom, I just apologize for making you think you needed to do this, you did not, but now you see you do enjoy it, so lets relax and enjoy each others body OK?"
Karl smiled and nodded yes. I held my cock and started moaning and humming while I stroked Karl's thighs. "Karl you have been so honest about your younger years, so tell me have you ever played with or even tasted your own cum?" Karl responded "No honestly Mike I have not but I did think about it and I did wonder what it would be like"
I gently stroked his body while stroking my cock, I knew he liked the feel of me touching him, I continued until he leaked a small pearl of pre-cum. Laughingly I said "Well Karl, here is your chance, you just leaked a nice little pearl, why not go for it?" Karl very slowly was struggling with the thought, he wiped his pre-cum onto his finger and finally brought it to his lips....
Next I told Karl to use the leather couch and take his favorite position he uses when he masturbates. Karl lied on the couch on all fours. I got my black t-shirt and laid it down on the couch. Karl knew what I wanted and started finger his ass. I touched him all over and he just moaned with pleasure as I touched him. I rubbed and kissed his sweet ass. I felt his smooth chest and spent a while stroking his thighs.
Karl, you seem to like being touched by a man, "Yes Mike, I never had a man touch me like you are, but I have thought about it when I wore my mom's stockings." "Karl let yourself go, imagine you are a girl, in fact I WILL FROM NOW ON CALL by a girls name when we are alone is that OK with you?" "Yea Mike I'm up for that Hmmm OK CALL ME KIMBERLY OR KIM I like that name"
"I like it also Kim, now we will go further, please cum for me, I will help you, but be a girl, make believe your cock is a girls clit, call it your clit, if you do I just may touch it, because after all you will be a girl and I would be touching a clit not a cock"
Kim now sat on the edge of the couch, and open his legs wide, he started wanking and he closed his eyes as his pleasure grew. All the while, I touched and felt him all over, he especially loved when I stroked and felt his smooth girl like thighs.
"Kim, don't be scared, but I am going to up this a bit" Kim just kept wanking and managed to moan out with "please do". I sad nothing, I got between Kim's legs leaned forward and forced my tongue into his mouth. He reflexively pulled back. I then grabbed him by the sides of his head, his hair brushing on the back of my hands and pushed him back preventing him from being able to move. I once more kissed him, after a few seconds, he surrendered , in fact he enjoyed being kissed and his tongue caressed mine. He went back to wanking and I back to groping. "Go ahead Kim, let your self just go "
With that I started getting very aggressive with my groping and stroking, He was starting show all the signs of nearing his climax, I kissed him once more and placed my hand on his and used it to wank him. He stopped the kiss and loudly said "Oh God Oh shit I'm goanna cum, I kept my hand on his but moved back as I of course wanted to watch. I let him go and quickly got the black shirt on the floor.
His climax started, his strings of cum were violent and large, his whole body got into it and he thrust his hips with each squirt of cum. "Good girl Kim, cum as much as you can for me, show me how much you like this and like me being your man"
Kim, just kept launching long violent streams of "her" pearly white creamy cum" Eventually his ejaculations died off and she caught her breath, the level.
Kim returned today about noon, she immediately kissed me and stripped. I told her to go get "dressed" in her stockings I gave her. We both were naked and sitting on the couch. I surprised Kim with some opiate hashish, he never smoked it before only ordinary weed.
Kim lets relax, try this, I know it makes me very horney and I am convinced it will do the same for you. We passed the small pipe back and forth and lit the hashish for each other.
I smoked far less than Kim, sneaky me, I wanted full control of her and the advantage of her being fully under the influence of the d**g.
Kim's reaction to the d**g was ideal, she felt mellow and dreamy BUT was very lucid and spoke as if she were sober. Kim said it was more a "body high for her, she said she felt euphoric and yes horney but not stoned. We began talking. "Kim remember yesterday when you tasted your pre-cum? You told me then you were intrigued and liked it some" Today let's advance, lets take a very large step only if you feel your ready"
"Mike, don't go on any further, I know where you are going, I am willing and even turned on by the idea but I am scared it is a point of no return, in other words if I do it, I can never be the same again" I talked to Kim, very calmly and encouraged her, I told her nothing is permanent, she is wrong she can always "go back" and just think of this as an experiment, kind of like young teens experiment with d**gs.
Kim said nothing other than to tell me to please stand as she moved and sat at the edge of the couch. I gently approached her with my throbbing cock, she just stared, I knew she was struggling with the idea but down deep she wanted to try it. Finally she pulled me to her by my ass, and placed her mouth on the head of my engorged cock. She froze for a few seconds, than as if she was experienced, which I knew she was not, she reflexively stroked and teased my cock head with her tongue. Finally she slowly took the throbbing hot shaft completely in her mouth. She did this very slowly and several times I had to teach her to be cautious with her teeth..............
Kim really listened well, she really wanted to learn. I then taught her about various ways to use her tongue and that she should use her hands to gently caress a mans ball sack and also stroke his ass or thighs.
Now since I am teaching Kim, I am really not approaching any sort of climax as my mind is occupied with teaching her and I really cannot concentrate on the actual pleasure.
"Kim, I think you learned quite a few things and I think you learned them well"
"Mike remember, I do watch porn and I just imagined what I would like if a woman were sucking me, so it was just a matter of putting all together"
"Good Kim , very good. Lets talk some and lets smoke just a little more than I will let you show me what you can do without any coaching from me, OH and BTW don't be afraid or anxious, I will leave it up to you whether or not I cum in your mouth. I realize that is a very big step, so Kim let me be clear, I will give you ample warning when I am about to cum and then you decide where you want my seed to end up. Also realize I feel it will be a large load so bear that in mind OK?"
Okay Mike I understand, I promise you I will use everything you taught me, Can I wank myself while I do you?"
"Kim don't be silly of course you can wank, I want you to have pleasure also, just as much as any woman I have sex with. I always make sure my partner get's her desires filled and orgasms"
We smoked some of the opiated hash, and then I spoke very gently and lovingly to Kim while I stroked her lovely hair and groped her smooth soft body.
"Mike, you woke something up in me, I never felt this way before other than when I wore my mom's stockings and panties, but this is 100 times more intense"
"So Kim I guess you are enjoying becoming a woman, am I right??"
"Yes you are, Mike I want to suck you now, please do not coach me, please just concentrate on the pleasure I hope to give you, only interrupt me if I do something wrong OK Mike?
" Yes my love, just do not forget, you choose where I cum"
Kim said nothing more she sat on the edge of the couch and asked me to stand. I did and she began to suck me. My God she was so into it, her tongue actually vibrating as she hummed and pressed it along the bottom of my cock, she did this while stroking her head for and aft along my throbbing cock. I held her face in my hands gently and just was in heaven as I felt her full silky long hair brush my hands and sometimes my thighs.
Kim would wank herself on and off, She stopped wanking and all of a sudden pulled me by mass and forcefully had my cock impale her moist warm mouth so deep that her lips pressed against my balls. Now she wanked herself non-stop. I opened my legs wide to make sure she had room enough to pleasure herself. She tickled the bottom of my cock-head with her tongue as she wanked furiously, then she went back to taking me as deep as possible once more. I felt her lips vibrate against my ball sack.
I was groping Kim's shoulders and thighs when I felt her body start to spasm, she was cumming and I could tell she was ejaculating a very large load as I felt some of her juice strike my knee and lower thigh. Also the spicy scent of her cum was so intense and her spasms lasted so long I had to look.
God her thighs and pelvis were drenched with her pearly juice. the sight of which brought me to climax, I held back and loudly screamed my warning to her. "Kim I can't hold out I going to cum right now" I was certain Kim would remove my cock and wank it to orgasm BUT NO, she just went wild and sucked me and tongued me.
My whole body trembled as I unloaded into her mouth, violent ropes of cum they were. All the more violent as they were sucked strongly as I shot, Kim immediately but gently squeezed my balls as if to milk my seed. Funny, she accepted my every rope but did not swallow, but rather just let my cum flood and eventually start to spill and flow down her chin and neck. I felt my balls become wet with my own cum. Kim milked every drop of my massive load. Finally I had to force her to stop. She did but kept me in her mouth as I deflated a bit. I realized now why she did not swallow, she was savoring the taste of my cum. Eventually she emptied her moth and just let my cum flow all over her chest and chin while she closed her eyes and rubbed it in like some sort of lotion.
"God Michael, you taste so sweet, I did not want to swallow, I wanted the taste to last, then I wanted your sweet creamy cum, I wanted to feel it on my hands and skin"
Kim told me she was certain she would not have had me blast in her mouth, but she tasted a drop of precum and decided right then she loved it.
Kim went on, "Michael your cum was fucking hot, I mean really warm, I loved it!!
"Kim lets shower, then I want to talk to you." We showered together, I kept playing with Kim's ass during the shower, even grinding my cock into the crack of ass cheeks.
"Kim, I want you to go home like yesterday get a nice long sleep, i'll give you some of the hash to help get drowsy if you like.
Now I guess you know what I would like us to do tomorrow yes?
"Yep Mike, I do and I want to experience it, BTW I already read all about it yesterday before bed. Don't worry I know all about the enema and douche, I'll be nice and fresh for you"
"Kim, you learned about anal ?? wow "
"I told you Michael, you awoke something in me and I want to experience it all"
Next day Kim arrived as usual a little past noon. She went straight to my bedroom and asked me to give her a few minutes alone. Finally she called me, God was I astounded, she was naked except for stockings and woman's high boots but the astounding part was she had applied some makeup to her eyes and a deep red lipstick. Nervously she asked how she looked. I did not answer but instead tore my cloths off as my cock sprang like spring. I grabbed her all over and groped her.
"Kim lets go slow, unlike yesterday, this you have to get used to and most of all be as relaxed as possible" I then laid on my back on the bed and instructed Kim to mount me in the 69 position with her boi-pussy in my face. I told her not to make me cum if she decided to play or suck, but I am doing this for a reason. Kim obeyed and I am now tonguing her anus. She is cooing with delight and slowly strokes my cock and also sucks on it every now and then. "OK Kim now get ready to relax your "pussy" as much as you can" I waited for a few seconds then I lubed my finger with KY jelly that I had taken to the bedroom with me. I then very gently and slowly invaded her with my finger. Kim let a sound that was part pain but also part pleasure I stopped when I was in her deep and we just remained motionless. "Kim, I want you to fuck my finger, make believe it is a cock and you are going to use your pussy to fuck it.
Kim said nothing, but she immediately started gyrating on my finger. She instinctively squeezed it tight with her anus muscles and it felt as if she were sucking my finger into herself. I also felt her cock throbbing my lower chest. "OK Kim, now just relax, I want you to feel something new and I promise it will not hurt any more than you feel now.
I found Kim's prostate after a few seconds and oh so gently massaged it. Kim was ecstatic and asked what I was doing, Kim said she felt like she would cum "Don't worry I would not be upset at all if you came, I would understand, but please do your best to not cum and wait for later. "Mike, OK, please continue doing that and I promise I will tell you to stop when I am close to cuming "
I then explained what I was doing, I explained about her prostate and how she will feel even more pleasure when my cock-head and shaft press on it later. I then explained edging to her, but Kim told me she does that all the time masturbating but she did not know it was called edging. We both kept at the massage while I kissed and tongued her ass cheeks.
"Mike I am relaxed, I can not wait anymore, let's do the "real thing"
"Good Kim, here is what we will do, this is your first time so, I will remain here on my back, I want you to squat over me , facing me, and lower yourself as slow as you need onto my cock, I will help guide you. I want to do this because it will give you complete control of every aspect. In fact it will be you who fucks me , you will control the depth, the force and rhythm all to your liking"
"Oh God that sounds so great, give that jelly let me use it and get my self nice and slippery" After Kim applied a very large dollop of the KY to her pussy, she lubed my cock and I almost came.
Kim now did everything as instructed. she held my cock with one hand and squated. She had perfect aim and I felt my cock head bear the pressure of her anus. "Ok Kim just go slow , we have all day and all night" Kim lowered herself just enough for my cock head to pierce her, she stopped and made a sound indicating that she was startled and eyes opened wide as saucers. "Kim believe it or not, but it will get easier from this point foreword just take your time. Kim listened and very very slowly lowered herself onto my large hard throbbing cock. She stopped many times and just stayed motionless, adjusting to how it felt. "Kim you are doing exactly what you should be doing, just take your time."
"Mike I don't know if you will understand what I am going to tell you, but I never knew I could feel pain and extreme pleasure at the same time, I love this, I never felt anything like this, honest Michael" Eventually Kim lowered herself completely onto my waiting cock. she stood motionless for a few moments , her eyes closed and she had such a dreamy and ecstasy filled face on her. Then I said nothing, she began to move slightly on my cock. She was amazing she combined sliding up and down with a rotation side to side of her thin hips. Of course she did this very slowly. "Kim open your eyes, I want to look into your eyes I want to see them as you feel more and more pleasure." Kim opened her eyes and her face expressed such ecstasy mixed with surprise. Kim was now feeling hardly any pain, it was all pleasure now. I know because I saw the ecstasy in her eyes and she started fucking me at a nice pace, gradually increasing the cadence. Eventually she would slam hard on her down stroke, moaning and sighing sounds of pleasure. She would slam my pelvis so hard that my balls would vibrate God that felt so good. I held her thighs and pulled her down now as I thrust myself into her. Kim is screaming with pleasure now, then a look of shock comes over her face, she is cumming, no hands cumming, her sperm shooting so fast and way past my head, I swear I heard two or three very violent ejaculations as they hit the bed's head board with tremendous force. Kim is crazy now.
The sight and feel of her cumming was too much. As she ejaculated every one of her violent strings, I felt her anus contract and actually suck my cock. "Kim , fuck me hard now I am going to cum, I am going to fill you!!" Just as I got the last word out I climaxed, I felt my cum shooting deep inside Kim, Kim never slowed down, in fact she sped up and her fucking became wildly forceful. "Mike I feel it, I feel it, I feel your cum shooting very high up into me" I don't know to this day how long I kept shooting large ropes of cum, but after a few seconds, my cum started to squirt out of Kim's pussy on each of her down strokes. Her ass cheeks and my thighs are drowned in a flood of my cum, Kim loved it I looked deep into her soft eyes as my strings started to diminish and finally stop. "Michael I l...) she caught herself I knew what she was about to say but she caught herself and did not finish the statement but her eyes did.
Kim was all woman now, though she swung both ways. I was the only man she would fuck but she did fuck several girlfriends. Kim remained my secret fem-boy for the remainder of her college years. At 23, Kim told me she had met a very kinky girl, when he went on a job interview in another state. "Michael, I know I will get that job, they just about said so, My girl Lois is very kinky, she pegs me sometimes with a really large dildo and also likes to be a dominatrix and I her slave. Michael we are going to marry" Kim just cried her eyes out that she had to move to get that job. We kissed and both understood all good things must eventually end
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