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Virgin Handjob & Introduction to Oral

Posted by: Age: 59 Posted on: 4 comments
7 likes 917 views Category: Masturbation Male-Female Tags: Handjob, Fingerfuck, Oral, Male-Female, Spy on sister
Introducing an inexperienced, but receptive, young woman to the excitement of sex. 

One summer, as a new hire at a government job, I met an attractive young secretary named Karen. After some office flirting it was clear that I liked her and she liked me. We began dating. Karen was about a year out of a Catholic girl’s high school and it soon became clear that she had not been with a lot of horny boys. Notwithstanding her limited experience, I discovered she was receptive to my roaming hands. Early in our dating relationship I had the great pleasure of reaching under the elastic waistband of her panties, moving past the erotic touch of her pussy hair, and finding her wet folds and clit. It was Karen who trained me in the art of bringing a girl to climax with my finger.

At this early point in our relationship I learned that Karen was not only a virgin in the traditional sense of the word, but she was also a hand job virgin. This was the 1970s and observant, obedient, nice Catholic girls did not do nasty things with boys. Karen had been so sufficiently indoctrinated/repressed that she was reluctant to take any initiative in sex. She was prepared to give in to the lure of accepting sexual pleasure but handling a boy’s thingy was a very difficult line to cross.  

But several dates in, there she was, in the afterglow of sexual release and in the immediate presence of this boy with a stinky finger and a bulge in his trousers. There on the couch I confronted her with the complaint that she never touched me. Karen recognized the inequity of the situation. With a gulp, she unbuckled the belt of my pants and pulled down the zipper. I trembled in anticipation. She carefully lowered my underpants revealing a fully erect dick. Her first view of a boner caused her to literally gasp, “It’s so big”. Actually, it’s average. After she spent a short time absorbing the dimensions of the problem, she placed her hand on this newly discovered monster. Surprisingly, it didn’t take very long for Karen to get the hang of it. She was soon stroking me with a nice rhythm.  

I was reclining with eyes closed enjoying the sensation when she broke the silence by asking me, “What is going to happen?” Instead of elaborating I simply said, “You’ll see.” A short time later I let out four or five spasms of projected sperm. Karen let out an emphatic, “WOW!” I don’t know why but it kind of pleased me that it made such an impression on her.  

Karen and I had a certain sexual protocol on the dates that followed. After a movie or a meal, we would return to my apartment and have a make out session on the couch that culminated in each of us masturbating the other in turn. When I suggested to Karen that we go into the bedroom, she would tell me that she preferred to stay where we were. Karen did not want to take any step that could possibly lead to intercourse. This young Catholic girl, living at home with her parents, was not going to get pregnant come hell or high water.  

Her fear of pregnancy led to another eccentric practice. Karen would not get nude from the waist down. If she was wearing pants, I would loosen the pants and reach down her panties. If she was wearing a dress, I would reach under it and then put my hand down her panties. Attempts to pull the panties off would be greeted with a, “No.” I masturbated Karen to orgasm 6 or 7 times without ever seeing her pussy. Her dark pussy hair would come into view as I maneuvered my hand to her wet spot but I never got a clear look during this period.  

I hear other guys describe themselves as a breast man or a leg man or an ass man. I like all those female parts but for me the most erotic part of the female body, by far, is that most female part. I really wanted Karen’s pussy to come into view so I put a new plan into effect.  

One Saturday night as we were reclining on my couch my hand was down her pants and inside her panties. I had captured wetness from her cunt and lubricated my finger. As I played with her clit I asked her the question, “Shall I kiss you here?” She did not answer. I think she was so surprised by the question that she wondered if she heard it right. I repeated the question, “Shall I kiss you here?” She then looked directly at me and asked, “You want to kiss me there?” Based on her tone I gathered that she thought I was asking to do something pretty nasty. Karen settled the question by saying, “I don’t think I’m ready for that.” I proceeded to finger fuck her to orgasm and she then beat me off.  

One week later, after a dinner at a nice restaurant, we were back on my couch in a familiar pose. I had my hand up Karen’s dress and inside her panties. Several minutes in to my massage of her clit I said to her, “I still want to kiss you here.” In the intervening week, Karen must have been considering the pleasure that might come from having a tongue in her pussy. Instead of saying no, she said, “You really want to do that?” I said, “I really do.” She then said, “If you really want to.”  

Even at this point we did not retire to the bedroom. Even so, I did not want some stoppage of the action to cause her to change her mind. I raised her dress above her waist. I then gripped her panties on each side. She raised her hips to allow me to pull down her panties. After I removed her panties, I was presented with a wonderfully sexy, but incongruous, sight. From her waist up, Karen was her stylish self. Covering her upper body was a high neck, long-sleeved, going to dinner dress. Below the waist there was not a stitch of clothes. When I spread her legs, I beheld my first view of a gorgeous large lipped pussy framed by dark brown hair. The dark triangle offered a dramatic contrast to the smooth, pale skin of her legs and abdomen. I would have liked to spread her lips and stare but I assumed she would be too self-conscious to allow me to do that. (I have called up the memory of this scene in numerous masturbation sessions over the years.)  

There was a lamp above her head. She put her arm towards the lamp but she was not close enough to reach it in her reclined position. I selfishly ignored her desire for the dark. I wanted a clear view of this lovely female gift. Karen was already wet from our earlier activity. I placed her legs over my shoulders and put my mouth to her cunt. I took in that unique smell of a clean, wet pussy. After tonguing the inside of her pussy and lapping at her lips, I moved to her clit. Karen was a girl who enjoyed the sensual pleasure of a guy playing with her pussy. But, to my considerable gratification, she LOVED having a tongue in her pussy and on her clit. She was rewarding me with audible intakes of her breath, almost whimpers. A few minutes in to this pussy smorgasbord, I remembered the advice to vary the stroke of the tongue when giving cunnilingus. As I treated her clit with swirls and circles, I received more inarticulate but clear expressions of pleasure.  

Alas, all good things must come to an end. Though I enjoy eating pussy, there is a fatigue factor associated with it. When I raised my mouth from Karen’s pussy, intending to finish her with my finger, she spoke the first English words that I had heard since I began this oral exercise. She said, “Don’t Stop.” Titillated by this erotic command, I went back to work. Fortunately, it only took a couple more minutes for Karen to let out an extended groan accompanied by some slight shuddering. It was the most wonderful orgasm that I had ever been responsible for.  

After a minute or so, Karen got up from the couch, picked up her panties, and then went to the bathroom. When she returned she sat down next to me on my right which was her usual masturbation position. With practice, she had lost all shyness associated with the extraction of my dick. She unbuckled and unzipped my pants and lowered my underpants and pulled out my dick. At this point, I put my face to hers and initiated a French kiss. I think I wanted to see if she still found me an acceptable kissing partner after my mouth had been on her pussy. Without any apparent reluctance she accepted my kiss and our tongues played together. When we broke our kiss she said, “You have pussy on your breath.” I asked her, “Do you mind?” She said, “Not if it’s my pussy.”

Karen began to stroke my dick which had become semi-hard from the break in the activity. When she got it fully erect, she looked at me and said, “I don’t want it to cum in my mouth.” Mind you, there had not been one spoken word about her giving me oral. I said, “I won’t come in your mouth.” She sort of gathered herself, lowered her head, and placed my dick in her mouth. This was clearly Karen’s first blowjob. After a couple of minutes, I spared us both and brought her up to a sitting position. She asked, “Didn’t you like that?” I said I did but that I would not cum that way. She then beat me off until the sperm erupted.  

After this session, Karen was okay with trips to the bedroom but intercourse was a long way off. In the interim, I pleased her with my hand and tongue. On rare occasions, she would take me into her mouth but a hand job was my usual release. I suppose most guys would have been unhappy with this result. But, for me, being masturbated at the hands of a pretty girl was a quite acceptable outlet.

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