Painful Beginnings

"My parent gave me my obligatory sex talk; it consisted of handing me a book entitled 'If Only They Had Waited' about a young couple who had sex, she got pregnant and that, of course, ruined their lives. Remember there was no contraception in those days, except condoms, which, of course, my parents would never condone for me and certainly never discussed with me, and pregnancy without marriage was totally frowned upon and usually resulted in the pregnant girl being sent away to relatives, giving birth to the baby then offering it up for adoption, before returning home after allegedly 'being away on a holiday', a euphemism which fooled no one.

"Anyway, I had no idea about the actual mechanics of sex. I had never seen a naked female. The closest I came was seeing my mother without a bra once, which was my fault, of course, and for which I was severely punished. I don't know how old I was when I found out that girls did not have penises, but I do remember this discovery vividly. We were at the beach visiting friends of my parents who were renting a cabin there and we'd been playing in the sand and returned to the cabin to change back into our clothes. The friends had a daughter, about 2 years old, and they stripped off her swimsuit and washed her down with a hose outside. She didn't have a penis!! This raised all sorts of questions in my mind. Was she deformed? Were all girls like that? These questions replaced the ones that were already in my mind about sex; questions such as how did the baby get inside the mother? I'd envisaged two penises rubbing together and something happening (at that stage I didn't know that the white stuff I ejaculated when I masturbated was responsible for making babies). How did the baby get out through a penis? That was one that had me totally stumped.

"So, I did some research in the library and there, in an encyclopedia (no Google then) were pictures of male and female bodies. The encyclopedia became my new best friend and I spent hours with my cock hard reading about males and females and sex, looking up such erotic words as pelvis, penis and uterus, and relieving myself by hand in the school toilets after each session. So now I had the basics of the mechanics of sex, about as useful as knowing fuel burns in rocket science.

"Further enlightenment came from a different source. As I cycled home one day I noticed a magazine rolled up in the gutter so, being curious, I stopped to pick it up. It was a girly mag, showing many pictures of scantily clad, well-endowed females. I perused that every night after lights out, using a flashlight under my blankets and masturbating to the photographs. There were no nipples or pussies, no nude pictures, because back in those days these were absolutely banned from publications. So that really didn't produce any more education, simply introduced me to the sexploitation of women to meet a demand by males for sexual titillation.

"By now I had my driver's licence and was attending a social group at church. There was a girl there who I quite liked but she wanted nothing to do with me. However, our parents knew each other and I was asked to take her home from the gathering each evening. On one occasion she was wearing black tights and I could clearly see the outline of her suspender on her thigh. Having viewed and masturbated to scantily clad females and seeing this in real life, I instantly became hard and after dropping her off to her home, I returned to mine and masturbated furiously at the thought of seeing her suspender, my imagination filling in the remaining details."

I laughed at the memory, Della's tinkling laugh joining with mine.

"So, when did you lose your virginity?" she asked.

"Patience, we won't get there tonight. I'll save that for tomorrow. Do you want a coffee or anything?"

"Yes please, black with one, thanks," she said.

I left the room and made two coffees, then returned with some cookies as well, placing them on the small table alongside her recorder.

"So, I've got a little ahead of myself in some respects," I resumed, "While I was in the final years of school my parents both worked and so I was home alone studying for exams for some of the time. I used these times to further my sexual experiences, although you'll probably find it disgusting and totally weird. I would go through my mom's underwear drawers and wear her elastic panty girdles, I think they were called, as well as tying my cock and balls really tightly. Psychologists would have had a field day had I been found out, which fortunately, I wasn't. I would masturbate and cum several times during these sessions, which usually took place on a private balcony where I would also sunbathe naked. Nudity was frowned upon at home; I can well remember when I was pre-school, probably about three or four, walking down the hallway from the bathroom after a bath and my father making the comment 'rudey nudey' as he passed. It's things like that, remembered for all those years, that really screw a person up.

"At night I would lie in bed and fantasize. In my mind I invented a whole country with a hierarchical system of government based entirely upon ranking people on the basis of the amount of gross body modifications they could tolerate. The head of the country had all his or her sexual body parts removed and regularly underwent very painful episodes to show how pain tolerant he or she was. Everybody else sought to emulate the leader and, in my mind, I went through all sorts of totally impossible scenarios as the character I was in my imagination slowly climbed the ranks. I would have had these fantasies for several years, I would think, but at some stage I must have given them up because I now only have their memory to haunt me."

I paused and sipped my coffee, nibbling on a cookie, and watching Della as she turned the recorder off.

"So, what about your story?" I asked.

"Similar in many respects to yours, but not so devastating, I would think. Obviously, society has changed between our generations and the current perception of modern youth is that we're a free-living, free-loving community of socially adept people who have no problems with communications thanks to the wonders of modern technology. Nothing could be further from the truth. Kids these days can be extremely judgemental and will put people down far more readily than they will praise people. This leads to most of the youth suicides and cases of depression you see now. Sexually, we have gone past the healthy stage, which was probably ushered in by the 60s sexual revolution made possible by the invention of the contraceptive pill and fuelled by such research as that undertaken by Kinsey and, especially, Masters and Johnson. The internet and the prevalence of pornography has changed the whole aspect of sex as well, many young people believing that what they see on porn sites is real and normal behavior. This creates yet another problem in society. While your sexual problems are a result of an over-puritanical mindset, I believe mine are the result of an over-judgemental and over-permissive mindset. Pity we couldn't stop half way between. The other aspect is one of increasing isolation of youth in particular, caused, ironically, by the proliferation of instant communication. Thus in an age where people are able to communicate rapidly and immediately over vast distances, they are unable to establish communication with the person sitting next to them."

I reached out and placed my arm around her shoulder. "I'll help you lay your ghosts to rest if you'll help me do the same for mine," I told her gently.

She tilted her head towards me and we kissed, long and lovingly. I felt her hand move as she placed it on my bare lower thigh. I placed mine on hers, feeling her warm smooth flesh beneath my fingers. I felt her kiss intensify and I slowly moved my fingers, easing them under her skirt hem, feeling a slight tremble of erotic anticipation, or maybe of fear, I didn't know. All I did know was that my cock was responding predictably.

We spent a while making out on the sofa, finishing our coffee and snack. Gradually, very tentatively, I eased my hand under her skirt until my searching fingers met the damp fabric of her panties. She, meanwhile, had gathered up the courage to rest her hand on my hard cock, then undo the zipper and place her hand on my undershorts over my cock.

"Does that feel good for you?" she asked as she slowly caressed my cock through the fabric.

"Yes, honey. What would you like me to do?"

"Take my top off, darling, then uncover my breasts," she whispered conspiratorially into my ear.

I removed my hand from where it had been stroking her pussy and used both hands to pull her tight top over her head. I then gently traced the edge of her flimsy bra over the tops of her breasts, kissing her as I did as she slipped her hand beneath the elastic of my undershorts and wrapped her fingers gently around my cock. If I'd been half my age I would have cum on the spot; as it was, it felt wonderful, as did her breasts under my hands as I explored them further. I reached behind her back and unfastened her bra, pulling the straps gently off her shoulders while leaving the cups in place. She kissed me intently again as I stroked her newly exposed back, her breasts, still covered by the cups, pressing against my chest. I felt her hand leave my cock and both hands unfasten the belt around my waist, undo the button on my shorts and then pull them open. She then moved her hands to the waistband of my undershorts, pulling that away from my body, out and over my cock, pulling it down and releasing it gently below my balls. She broke the kiss and looked down.

"So, this is the poor wee man who you abused for so long," she said wistfully, wiping a drop of precum from the end with her finger, which she then placed in her mouth. "Mmm, you taste nice," she commented.

"Yes, that's him, and I still do even now sometimes, but nowhere near as much as I did then."

"Well, maybe you can show me some time," she replied with a grin.

"Yes, or maybe you can do it for yourself," I grinned back.

I moved my body away from her and removed her bra, gently cupping her firm, soft, silky smooth globes and nipples. As I watched, her nipples hardened, possibly from cold, possibly from arousal or maybe both.

"Has any man played with these treasures before?"

"No, never," she admitted, looking down again shamefully.

"Well, I feel very privileged. They are absolutely perfect, absolutely beautiful."

She kissed me again, then replied. "You say the nicest things, darling. Do you think we could go to bed? It would be more comfortable."

Who was I to argue with a willing woman? I stood, held out my hand, which she took, and we walked into my bedroom. I quickly stripped the covers off, picked her up and laid her on the sheet. She remained still, grinning as she looked up at me, her top half naked, bottom half with skirt awry and damp panties covering, but doing very little to hide, her mound. I looked at her for a few seconds.

"God, your gorgeous," I told her.

"Thank you, darling, you're pretty good yourself," she replied, reaching for my cock, projecting towards her, held in place by the elastic beneath my balls. She stroked it gently, then rolled towards me and used her other hand to cup and caress my balls.

"We'd better take these off, I guess," she said, then laughed, "Your shorts, not your balls."

I joined her in laughing as she slid my shorts to the floor. I assisted by stepping out of them, then unbuttoning and removing my shirt, leaving me standing before her naked.

"I can see why you like being naked," she said, "You look gorgeous naked."

"I'm sure you will too," I replied, reaching down and rolling her onto her side, then unfastening her skirt and sliding it downwards as she raised her hips. Her panties were brief and hid very little, especially where they were wet from her arousal. I gripped the elastic and slowly lowered them down her legs as she raised herself off the sheet. Naked, she looked beautiful, a peach ripe for the plucking, or fucking in this case, I thought. It was hard to believe that a young woman who looked this good could have escaped the attention of all the sex hungry males out there and be waiting here for me.

"Now you're sure you want this, Della?"

"Oh, yes, honey, fuck me, take my troublesome virginity, make me a woman, please darling, do it now."

I took a towel from the drawer and placed it under her ass. "You know that you may bleed a little when I penetrate you, and that it may hurt a bit, don't you?" I asked.

"Yes, honey, I know the theory, it's just the practical that's missing."

I climbed onto the bed and she parted her thighs, giving me full access to her beautiful, sparsely covered pussy. I stroked it gently before easing my finger into her tight opening.

"Have you used tampons or masturbated or used a dildo?" I asked.

"No, never. I wanted the first time to be perfect so I am intact, my hymen is still in place. And don't worry, I've been on the pill for years to regulate my periods, so I won't become pregnant and have to be sent to an aunt's place in the country," we both grinned at the memory of my words earlier.

I knelt between her soft thighs, lifting her knees to bend her legs, then pressing them gently sideways to open her up as far as possible. I then slid my finger into her gushing entrance and was stopped just inside by her obviously intact maidenhead. I felt my cock give a lurch, preparing itself for the task ahead. I bent my head forward and kissed her nipples, opening my lips to suck each one in turn. From the corner of my eyes I noticed she rolled her head and I heard her gasping for breath as she felt the unaccustomed stimulation. Then, while still nibbling her nipples, I pressed my hips forwards so the end of my cock slipped easily between her well-lubricated labia and entered the entrance to her vagina.

As soon as I was in position, I pushed forwards on my voyage of discovery and before my head was even properly inside I felt the resistance of her intact hymen. I looked into her eyes.

"This is it," I told her, "You're sure?"

"Yes, honey, break it. Push your gorgeous cock deep into my virgin tunnel where no man has ever been before."

I grinned at her description of her potential deflowering, then pushed, hard. Her face screwed up and she bit her lip in pain, but made no sound; neither did my cock make an entrance. I relaxed; so did she.

"You're pretty tough," I said.

"Yeah, but I know you're tougher. Come on, honey, do it, please."

"But I don't want to hurt you," I replied.

"Sometimes you have to be cruel to be kind. Look at the pain that you've caused to be inflicted on your story characters. Hell, a small thing like taking a person's virginity is nothing compared with your bdsm sagas. Push him in, take no pity. Come on, darling, do it."

She was right, I knew; however, the painful sessions in my stories were fiction dreamed up in the blackness of a damaged mind; this was reality and I really did not want to hurt this beautiful young woman. However, needs must, as they say. The hymen wasn't going to break on its own and there was nobody else here to do it for me.

I spread her legs wider apart then lifted her hips with the towel and placed a pillow underneath. At least I could allow gravity to assist me, I thought as I repositioned myself and fitted the head of my rigid cock back into position.

"You ready for this again?" I asked.

"Yes, honey, do it. Fuck me."

She placed her hands under my ass cheeks and as I tensed my muscles to thrust I felt her pull upwards hard. As the pressure increased she once again bit her lower lip and screwed her face up in pain, then she pulled hard with her arms. I redoubled my effort, pushing as hard as I was able until with a rush my cock penetrated her and forced its way deep inside her no-longer-virgin cunt.

Della screamed, a long, pain-ridden, high-pitched scream. I held still, fully inside her, far further than I had intended for my initial thrust. She looked up at me and smiled, a full, happy, relieved, though painful smile.

"Thank you, sweetheart, oh thank you so much," she said, pulling my head down and slathering my face with kisses.

I remained still for a while, letting her become accustomed to an intruder inside her, then I began tentatively withdrawing.

"No, don't take him out, he feels so good inside me."

"I'll put him back, honey, promise. Movement feels better than just remaining still, you'll see."

I began slowly thrusting in and out in the ageless rhythm. Despite this being her first experience of intercourse, Della picked up the rhythm quickly and met me thrust for thrust. Gradually she became more aroused, made more sound, groaning in pleasure, her breathing increased, she began writhing and moving her hips to gain more stimulation, then she stopped.

"I need to pee, honey," she said desperately.

"No, you don't, you need to cum. It feels much the same, I've been told. Just let it happen and enjoy."

She relaxed and we resumed our rhythm, Della quickly reaching then surpassing her previous point of arousal. She began rolling her head from side to side, her hips pressing into mine, forcing her clit against my hairy pubic bone, then she seemed to explode. He legs rose, arms extended, she let out a shriek and began shuddering beneath me as her first orgasm through intercourse hit. I pressed into her and held there as she came to pieces around and beneath me.

Slowly she relaxed and gazed into my eyes.

"Is that what I've been missing?" she asked.

"It would seem so. Tell me, have you masturbated or had any previous orgasms?"

She looked away. "No, never. That's my first, ever. God, it was great. Can we do it again, right now?"

"Of course. I haven't cum so I'm still rock hard and ready to go."

"Ooohhh, goody," she giggled like a little girl being offered another fun fair ride.

I quickly resumed our rhythm and she settled to the very pleasant task, thrusting at me in time with my thrusts into her, the feel of her silky vaginal walls against my cock was amazing, especially combined with the knowledge that I was the first to feel them. I felt her arousal increasing again as she approached a second cumming. I was having trouble myself holding my orgasm at bay and knew I could only do so for a few more strokes. I was about ready when she tensed, gave another, quieter shriek, and began shuddering and writhing beneath me. That was all it took; I felt my cum being forced through my cock and filling her hungry love tunnel as I pumped jet after hot jet of cum against her cervix. That pill had sure better be working, I told myself as her writhing took on a new dimension, probably from the feeling of me lubricating her inner passage for the first time.

We lay together recovering, my cock softening and shrinking as we held each other, kissing sweetly and lovingly. Eventually we parted, I carefully wiped the small amount of blood off our crotches, then we sat up.

"I need to pee, for real this time," she said, walking to the en suite bathroom. She took a while, then returned, grinning.

"I used to only be able to push my finger in a little way but now it goes all the way in," she said, showing me her wet, slightly bloodstained finger, which she wiped on the towel.

"Yes, you're now open for business, whenever you choose to be. Now you can choose a great boyfriend without the embarrassment of being a virgin."

"Yes, but, um, I am here for the weekend, right? We can do this again? You're not just kicking me out now, are you?"

"No, of course not, sweetheart, we've got lots of playtime left this weekend. Besides, you've only got the very beginning of my story."

She relaxed and climbed into bed with me, cuddling into me and drifting quickly off to sleep. I looked at her in the dim light coming through the blind as she lay in my arms, imagining my daughters lying in their lovers' arms, watching the sheet over her rise and fall gently with her easy breathing, and finally drifting off to sleep myself.