Chapter 1: The Question
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, First, Oral Sex, Petting, .
Desc: Erotica Sex Story: Chapter 1: The Question - Dawn's parents ask a family friend to ensure their daughter does not die with any regrets. Dawn wants to lose her virginity before she dies and the friend is asked to help with this delicate task.
Alex and Di are good friends who I meet up with once a month, usually for a pub meal or BBQ, and we catch up on each others news - work, life, recent trips and experiences, and families, etc.
We met in O'Brien's Irish Bar close to their home for a few beers and a meal after work. The first pint slid down easily after a long day at work and after getting another round of drinks in we started to talk more as our immediate thirsts were quenched for now. The conversation seemed a bit stilted and hard work as they seemed quite sullen and spent a lot of the time looking at the table, rather than making eye contact. After catching up on how each of us was doing at work, I suggested we order dinner as I was hungry and it also gave me a break to go to the bar and order. I was hoping that if they had had a disagreement previously then they would brighten up by the time I got back to the table.
As we sat making our beers last until the meals arrived the conversation did not pick up and something was definitely wrong. So rather than having a miserable evening I asked if everything was OK, and at which point Di started crying quietly.
'Oh shit, ' I thought 'they are splitting up."
"We have a problem," stated Alex, "Dawn has been diagnosed with stomach cancer."
"Oh shit," I blurted out.
"She has been given two months to live," Alex continued," and two weeks of that has now gone."
"I don't know what to say to you both, apart from I am very sorry for all of you and if there is anything I can do to help, in anyway, just say anytime day or night," I said in shock.
Dawn is Alex and Di's only child, a shy, quiet 19 year old who was going through university until this came up.
Alex finished his beer, so I signaled for 3 more as I didn't want to leave them while I fetched them. The telling of the news seemed to have drained Alex, and Di eventually took up the conversation after a long silence.
"We took Dawn to Hawaii last week for a holiday as it is a place she has always wanted to visit and so we did it while she was still well enough to travel," Di took a sip of beer before continuing, "We had a great week together and spent most of the time talking as we felt time was slipping away. We all wanted to ensure that we had said all the things we wanted to say and express our love for each other. One evening over dinner we were talking about none of us wanting to die with any regrets and that the month should give us time to ensure that didn't happened. Alex asked Dawn if she had any regrets and if so, could they be resolved. Dawn said she had one regret and hoped that it could be solved."
For the first time both Di and Alex looked up at me and looked straight into my eyes before turning and looking at each other. They gave each other a slight nod before Alex turned back to me.
"You asked if there was anything you could do, were you serious?"
"Shit, yes," I instantly responded, "I known you all over 15 years and you are special to me. I will do absolutely anything you want to help you and Dawn especially... money, treatment, transport, anything just say"
They looked at each other again and nodded to each other again. This time Di spoke, "This is a mummy type of question and it needs to be me to ask it."
I sat quietly and waited for the question, desperately wanting to have a swig of beer, but sitting still waiting for the question.
"I would... I would like to... How can I say this?... Dawn's only regret is that she doesn't want to die a virgin," Di finally blurted out.
I stared silently at them, my mind a whirlwind trying to ensure I had heard and understood them. If I said the wrong thing now I would possibly spoil a very special friendship and make a nightmare for them. I wasn't totally sure that I understood the question as it was more a blurted statement. I took a sip of beer to buy myself some more time.
At this point the meals arrived and this gave me a couple more minutes as the waitress set the meals down and made sure we had all we needed.
"I don't know what to say," I finally responded, "as I am not sure what you are asking."
"Dawn is very quiet and shy and very religious. She doesn't have a boyfriend even though several of the boys at church have asked her out. She feels that if she lost her virginity to one of the boys, it wouldn't mean much to them, and so they wouldn't make it special for her," Di explained, "Dawn wants it to be someone she trusts who will love her, treat her gently, and make her a woman as she puts it."
Yet again they looked at each other and nodded, but this time Alex spoke.
We would like it to be you who makes love to Dawn for the first time as we trust you to treat her right."
'Fuck, ' I thought, suddenly realizing the insensitivity of that particular thought.
"I am 40," I stated, "and Dawn is 19."
"That is why we chose you, because you care and you love her as a friend and our daughter," Di added.
"Wow", I responded," Do you mind if we eat while I try to take this in?, I am stunned."
Without out waiting for a reply, I started my meal as if that most amazing conversation had never taken place. Had two pints of beers given me an out of body experience? The look of Alex and Di's faces as they ate told me otherwise.
"Did Dawn ask that it be me?" I asked part way through my main course.
"Not exactly," Di answered, "but she went on to talk about you afterward at great length, to give the suggestion that she would like it to be you, but she was too shy and embarrassed to say or ask."
What do you say to two great friends in their hour of need when they honestly ask you to make love to their dying 19 year old daughter?
I thought long and hard as I finished my meal. I had never made love to someone that much younger than myself, would I be good enough? On reflection that was a silly question as she would have no one to compare me with. What a stupid selfish thought, I bollocked myself for the uncaring thought.
"When I offered to do anything I meant it, but this has stunned me, and I am amazed that you would ask me." I said quietly.
"Does that mean 'No'?," Di asked.
"No, it means I am amazed and truly honoured that you all should trust me so much to ask such a hard question," I stated still in shock, "How would this work?'
"We would leave it entirely to you to decide, does that mean you will help?" Alex asked.
Yes, I would be proud to, and I will take the greatest care of Dawn. But it must be on the understanding that if she changes her mind, it stops with no hard feelings," I answered.
"We wouldn't have it any other way, Thank you very much," Di sobbed, "You are a great friend. Di leaned across the table and gently kissed my cheek.
My mind wandered and thought that the next person to do that would be her daughter, as I was damn sure Alex wouldn't be giving me a thank you kiss!!
We ordered another round of drinks as we loosely discussed the best way to make this happen. After that I whistled up 'Dial-a-Driver' to get me home as I had drunk more than normally and I was still probably in shock.
In the morning I had the car valeted at work and had a courier pick up my overnight bag. About three o'clock I turned off my computer and made use of the company showers to freshen up and look the best that my 40 year old body could. Looking at myself in the washroom mirror I couldn't believe what I was going to do. Seriously, I thought I was helping out friends with a much needed favour. I did not consider I was going out to screw a 19 year old girl. I was going out to make a friends dying daughter a woman.
I parked my nice shiny (and unusually clean) wagon outside the university building where Dawn was meeting friends and waited for her to emerge to catch her bus home. When Dawn emerged and caught sight of me, she was pleased to see me and gave me a big beaming smile as I stepped forward to hug her gently. I thought of her as a fragile china doll, rather than a good looking 19 year old who looked good in a cheese cloth shirt, tight faded jeans and sandals.
"What a surprise, what are you doing here?" Dawn asked, "Are you selling your car, it isn't usually that clean?"
"No, I cleaned it specially," I replied with a smile, "as I am taking out a very special lady for dinner tonight."
Dawn punched me gently in the stomach and asked "Who?, come tell me, tell me now!" as she smiled brightly, her face a picture of radiance.
"You my lady, I am taking you out for a very special meal and evening," I smiled back.
Dawn looked stunned, "Me?" she asked.
"Yes you," I replied gently punching her arm in return, "Now get in the wagon and put your belt on."
Dawn jumped in the wagon and looked at me quizzically as I entered the driver's side. The stereo played her favourite band as we drove down to a harbour side pub and dumped the wagon in a car park.
The pub was empty for early Friday evening and we sat on high stools over looking the harbour as we drank fruit cocktails and laughed at the surprise on her face when I picked her up. We chatted easily for a couple of hours, and I became more relaxed. After the third drink I took her hand and said "Time for dinner young lady" and headed next door to one of the top seafood restaurants in town. This was Dawn's favourite restaurant for birthday treats, and it had a relaxed atmosphere and dress code.
We were shown to our table which had a lovely bunch of prearranged roses in the centre for Dawn. I ordered some drinks as she looked at the roses and then me as she read the card, which said simply 'To a great evening with a lovely woman.'
I smiled in return and said what I fancied to eat for dinner. The menu was superb and we were rewarded with an outstanding meal as the sun set over the harbour, and we shared a nice bottle of wine. We talked about all sorts and everything except her illness. Over desert we spoke about her special holiday in Hawaii. Her face glowed at the memory and the things she had enjoyed with her parents.
When she finished I asked, "No regrets then?"
Dawn looked at me in surprise," What do you mean?"
"Dawn, when we have finished dinner I would like to take you for a walk along the harbour, holding hands, and at the end of the harbour wall kiss your sweet lips." I smiled sincerely at her as she thought about our conversation and slowly started to understand.
After coffee Dawn stood and reached out for my hand, I was relieved. I paid the bill and led Dawn out into the warm evening air.
As we walked I held her hand for a short time before letting her go and placing my hand on her shoulder and pulled her into my side. Before we got to the end of the harbour wall I stopped and turned to her. I leaned down to gently lift her chin to mine and kiss her lips. I gently slid my arms around her waist and eased her gently to me. I kissed her softly and eased my tongue against her lips. Fortunately Dawn responded and hesitantly let me slip my tongue into her mouth. Her body relaxed as we kissed for several minutes ignoring the rest of the world entirely.
Eventually we broke for air and Dawn looked into my eyes, displaying a need to be loved in a physical sense.
"Do you see that room on the top of the Marriot across the road?" I asked.
"Well I have booked that penthouse for the evening and I would like to invite you up there to enjoy the evening with me," I quietly stated.
"Oh," she replied, clearly surprised and taken aback.
"Would you care to join me?"
"Yes... Yes I would," she responded and my heart danced. I don't know what I would have done if she had said no. Plan B was to take her home if she had declined. Fortunately there wasn't need for plan B at the moment.
We held hands as we crossed the road and walked into the foyer. I had already sent ahead instructions and a photo so the desk staff would pass over the key and forgo the bellboy showing us to the penthouse.
In the lift I held Dawn's hand and she felt nervous as the lift rose to the top floor. The lift opened directly into the room using our key card. There was subdued lighting in the room allowing the lights of the harbour and waterfront to flood in through the windows.
We walked through the room and out onto the balcony overlooking the water. I stood behind Dawn and gently kissed her neck as we looked out in the warm evening air. My hands slid down onto her hips as I kissed my way around the back of her neck, brushing her shoulder length brown hair to one side as I traversed the soft warm skin from ear to ear. Dawn sighed as I reached her right ear and gently chewed her lobe as I started to turn her around and continue my journey towards her warm lips.
As my tongue slid into her welcoming mouth my left hand slid up her back to rest between her shoulder blades and pull her so her lithe body rested against mine. My right hand slid down onto her hip and the fingers rested against the seam of her jeans between her cheeks, softly feeling the curve of her bum.
As we explored each others mouths and my hands softly caressed the warm body beneath them, I could feel Dawn respond with warmth and passion. My left hand stroked through her hair and onto her cheek as I tenderly kissed this young innocent girl. I didn't want to rush in any way so I let my right hand slowly descend over her denim encased cheeks to caress her bum as I kissed her for several minutes.
Finally we eased our lips apart, but held onto each other, Dawn's hands around my waist. Looking deep into her eyes I whispered, "I would love to make warm, tender passionate love to you tonight," and kissed her briefly again.
As our lips parted again, she breathed "Yes,... I would like that very much."
I leaned down to kiss her again, relieved with her answer, and growing horny to this lovely 19 year old that had just melted in my arms, giving me the answer I needed to take her in to womanhood. I was now in a very fortunate and trusted position of teaching this young girl the beauty of sensual lovemaking and maybe follow it with several lessons in the art of exciting sex.
There was a deep passion and longing in Dawn's lips and body as we kissed harder and more urgently than before. I didn't want her to change her mind by me rushing her as this was all new to her. As we kissed I let both hands roam over her bum, feeling its tight, firm shape under the denim as I squeezed and molded her cheeks. Dawn started to caress my back as your tongues explored each others mouths and lips as we occasionally took the odd breathe as our passion grew. Slowly I brought my hands up over her shoulders and reached down to undo the top three buttons of her blouse, pleased that Dawn sighed gently into my mouth as I did so. Feeling her acceptance I continued to undo the rest of the buttons before finally pulling the blouse out of her jeans.
Breaking away from her lips but holding on to her hips I started to kiss her chin and down on to her neck. Slowly I eased her collar apart so my lips could trail down onto her shoulder as I eased her blouse apart further to expose more of her smooth virgin skin. I wondered if she had let anyone do this amount of kissing before, but I doubted it as I gently nibbled the smooth warm skin of her shoulder.
My hand slid under her blouse to rest on her smooth back as I slowly knelt in front of her, bringing my mouth to just under her bra as I started to kiss her stomach and rub her back and Dawn slid her hands onto my shoulders. Looking up I could see her young breasts swell and heave in her bra as her breathing became deeper. I tilted Dawn forward with my hands and stretched my neck to kiss the underside of one of her bra encased breasts. She sighed and closed her eyes as I ran my tongue over the material and gently used my teeth to press into the firm flesh underneath causing her nipple to harden and show itself through the material. As it hardened I transferred my mouth to her other encased breast and my hands smoothly pulled her loose blouse down her arms and off her back, letting the material fall to the floor in the warm evening air.
Dawn transferred her hands to run through my short cropped hair giving me the signal to reach behind her and release the clasp of her bra and begin to tug the cups of her bra away from her breast with my teeth as my hand reached up onto her shoulders to slide the straps slowly down her arms.
Her bra fell away over the back of my head to reveal a beautiful pair of young firm breasts that stood proud and erect on her chest in the reflected light of the evening. My neck stretched up to begin kissing the under slope of one breast and slowly take her nipple into my mouth to Dawn's sighed approval. I was pleased to find her breast was more than a mouthful in size and guessed them to be about 34C in size as my teeth grazed across her nipple. I sucked firmly on her breast as Dawn pulled my head in closer and I ran my fingernails gently up and down her spine.
As her nipple swelled fully erect my lips ran onto the top slope of her breast before moving off into the soft shallow valley between her breasts. My tongue wetly lapped the smooth skin of her breast bone as it slowly started the ascent of her other breast towards the cherry red nipple astride the summit.
I sucked, teased and nibbled her nipple for several minutes, sometimes sucking her whole breast deep into my mouth, whilst running my hands down onto her bum to feel it's wonderful firm cheeks. As I again transferred back to her other nipple I eased my hands around to the front of her jeans and undid the button before easing the zip down. Sliding my hands into the waist band onto her hips I slowly started to ease her jeans down while still teasing her nipple with my tongue. My hands ran over the warm materials of her panties on her hips as her jeans descended and I felt the skin of her upper legs. As her jeans passed her knees Dawn stepped out of her jandals and out of her fallen jeans, all the time supported by her hands on my head and my mouth clamped securely to her breast.
As she finally stood before me in just her panties I raised myself up and hugged her to me as I kissed her deeply. Finally I broke the kiss to take her in my arms and carry her lovingly inside our penthouse and take her to bed.
I gently laid her down on the king-sized bed with her legs hanging over the end of the bed and resting her feet on the floor. I leaned over her to kiss her passionately on the lips for several minutes before slowly starting to kiss my way down her body, traveling down across her soft warm neck and slowly back onto one of her breasts. I resisted the urge to squeeze her other hungry horny breast with my hands as I only wanted to pleasure her with my tongue and focus her pleasure in one place at a time.
Dawn's hands rubbed passionately my head as it trailed kisses over her flat stomach and stopped above the top of her panties. Tenderly I licked along the top edge of her panties and stomach before standing and walking around to the bottom of the bed and kneeling at her feet.
Leaning forward I softly kissed each of her knees before starting to trail kisses alternatively up her legs. As I did so Dawn slowly eased her legs apart so I could lower my kisses down on to the warm firm skin of her thighs. As my head got between her thighs I could smell the warm sweet scent of her pussy six inches in front of my nose.
Dawn eased her legs further apart before finally placing her legs on my shoulders to give my head room to reach into her crotch. Finally I had to place my hands on the back of her calves to steady myself as I nibbled the sweet flesh of her inner thighs. I could hear Dawn starting to pant and felt soft trembles through her thighs as her hips rocked on the bed. Her hands reached down to grasp my head and try to pull me closer to her panty encased crotch.
After several minutes of kissing and admiring her thighs I eased her legs apart a bit further, opened my mouth wide and clamped it down over her panty covered mound. Dawn arched and moaned as this increased teasing guided her towards orgasm. I guessed that being so religious she would have seen it as a sin to touch herself, so I figured I was taking her towards her first orgasm, and I wanted to do it in style.
My mouth squeezed through the material to increase her pleasure and frustration as her hands instinctively pulled my head down hard onto her mound. Finally and suddenly I shot my tongue forward pushing the material into the fold of her lips. This action broke the dam as her panty crotch became sodden with her juices and Dawn arched up off the bed as her first orgasm ripped through her. She screamed and wailed aloud as this unknown sensation attacked her body. As she orgasmed I gripped her hips so I could keep my lips in place as my tongue started to lash up and down the material now deeply pressed into the folds of her pussy. I wanted to keep her orgasm going so I slid my hands under her bum to cup and squeeze her cheeks as I sucked on a virgin pussy hidden below her sodden panties.
As Dawn finally subsided I started to ease her panties down and she arched her back to help their descent as the sodden gusset eased out from between her pussy lips.
After removing her panties I stared and admired the wet virgin pussy glistening in front of me. To be honest I wanted to plough my tongue back into it and just feed on her juices all night, but this evening was solely dedicated to Dawn's pleasure not mine.
I stood up and moved round to kiss her on the lips so she could widen her experience by tasting her own virgin juices. As I pulled my lips away after a long satisfying kiss I reached down to cup her mound in my hand, and softly asked "Are you ready to be taken into womanhood my love?"
Dawn nodded slightly and a soft "Yeesss" escaped her lips.
I stood and walked to the end of the bed, removing my clothes in as dignified manner as possible, not wanting to look that I was desperate to sample her pussy and take her cherry. My cock was rock hard as it was finally released from my boxers and pointed towards the young virgin in front of me with the hot pussy that seemed to say 'Come fuck me.'
I eased my arms under Dawn's knees and lifted her legs off the floor so her thighs and pussy were spread wide as I eased myself between her soft thighs. I ran my index finger down the length of her pussy several times before carefully easing it inside as I asked "Does that feel okay?"
"Oh, Yeesss," whimpered Dawn.
Her pussy was moist so I extracted my finger and reached up for both of her hands. I gently placed her hands on my hard prick and wrapped some of her fingers around my engorged length so she could feel my balls hanging underneath, full of spunk and ready for action.
I heard a sharp intake of breath escape Dawn's lips as she felt and handled her first prick. I think she was shocked and surprised. It is only any average sized prick but shy Dawn just wasn't aware of the aroused male body.
I eased forward and cupped my hands over Dawn's as I nudged my prick against her sodden pussy lips. Gently I rubbed my prick up and down her lips to ensure the head of my prick was lubricated with her juices before I pealed her hands off my prick in preparation of taking her cherry.
"This will stretch you open as I enter you and you get used to me being there. Are you comfortable and ready?" I asked.
Dawn nodded, so I increased my grip on her bum cheeks as I eased my hips forward and spread her lips as the head penetrated this wonderful young girl who was about to become a beautiful young woman.
Dawn winced slightly and moaned as her lips spread to accommodate my girth and I rocked forward and back slightly so she could get used to this new feeling and experience. Slowly I increased my penetration until I brushed up against her hymen. I felt a very fortunate man being allowed the honour of easing Dawn into womanhood as her cherry was ready for popping.
"Are you ready for a bit of pain and discomfort briefly before we share the most amazing sensations in the world?" I enquired.
Again Dawn nodded and I pulled my hips back a little before easing forward in one steady but firm stroke to take away her virginity and take her into womanhood.
Dawn screamed and bit into her hand as her hymen gave way and my hard solid prick filled her pussy. I leant forward to kiss the tears from her eyes before kissing her softly on the lips. As she adjusted to my prick inside her I held still as the passion of our kiss increased. Over the next minutes Dawn started to draw hungrily on my mouth and dug her nails into my shoulders. I could feel her pussy lubricating itself around my prick so I slowly eased back to withdrawal, for my next thrust. Dawn's eyes stared at me in panic as she pulled her lips off mine and pleaded "Please don't take it out so soon."
The poor naïve beauty did not know the first thing about sex.
"It is okay, I'm not going to pull out of you all of the way, I am just going to leave the thick end just inside of you briefly before I push it all the way in again."
She looked relieved at my reply and the way I slowly slid forward to fill her again.
For the next couple of minutes I carefully slid my prick in and out of her incredibly tight pussy. Dawn started to glow underneath me as the face of a shy naïve religious girl slowly changed into the face of a sensual young woman. I held the tops of her thighs against me as I steadied my rhythm and stroked in and out.
Dawn's juices flowed as her tight pussy slowly loosened, and I started to push a little deeper into her so my balls started to slap against her bum. I could feel an orgasm starting to build in Dawn as she returned my thrusts, letting natural inborn instinct take over. I started to pick up the pace as her orgasm grew and reached forward to place my hands on her heaving breasts for the first time. This extra stimulation sent her over the edge into her first orgasm as a woman and second orgasm of the evening.
As Dawn bucked and screamed in her excitement I kept up a steady pace and firmly squeezed her firm breasts between my fingers. It was an outstanding sight watching Dawn enjoy her first experience of sex as her eyes fluttered during the intense pleasure of her orgasm. Her tight pussy clamped hard down on my prick and throbbed around its entire length. God, it was hard not to shoot my load into her hot snatch there and then. It may sound vain but I wanted to give Dawn the ultimate experience of her life by fulfilling my role as the experienced older man, rather than it being some young pup giving it the 'wham, bam, thank you ma'am' on a Friday night. I wanted to pleasure her and fuck with style and grace as too many people remember their first time as being hurried or disappointing. I wanted this to be neither of those things for either of us.
I roughly squeezed her extended nipples between my thumbs and forefingers to extend her heightened awareness and pleasure. I was tempted to reach down and finger her clit, but I would save that pleasure for later.
Tears rolled down her face and I became very concerned, but she quickly smiled with love in her eyes to reassure me as I started to ease towards my own orgasm.
Now that the 'deed was done' so to speak I wanted to teach Dawn everything about lovemaking and sex all together, but I reminded myself to go slowly and carefully.
I kept one hand slowly massaging her breasts and nipples as I slid the other under her exquisite bum to grip one of her cheeks and slide my fingers into the damp cleavage of her bum. My middle finger stretched to reach her tight puckered anus and started to rub some of her juices dripping from her pussy around her tight ring.
Dawn started to squirm as my finger lightly probed her hole and introduced yet another sensation to her. I checked to see if she was comfortable with what I was doing, only to see her loving smile still in place. I wiggled my finger gently to stimulate her arse without entering her.
The stimulation to her arse, breasts and the steady pounding of my prick and balls was quickly bringing her to another orgasm. My prick slid easily in her saturated pussy as the come in my balls started to boil.
"Yes... Yes... Yes... Yes," I slowly chanted as I got ready to fill this wonderful young woman's throbbing pussy with my boiling hot seed.
Dawn matched my thrusts with her body, and my quiet chants with quiet "Yes" chants of her own.
I took hold of one of her nipples in my fingers, and increased the pressure on her ring with my other hand so my finger started to stretch it a little, causing Dawn to launch into her orgasm at the same time my come started to explode out of my hot balls. I buried myself up to the hilt in her pulsating pussy as I shot wad after wad into the neck of her womb. Her legs and feet beat on my hips and arse as she shook, throbbed, heaved and sweated through her orgasm. Dawn's pussy muscles seemed to want to choke the life out of my burning prick as we both yelled "Yes, Yes, Yes" in our pleasure and satisfaction. I looked in wonder, love, lust, and amazement as we shared a mind blowing orgasm that drained all of our energy down into our sopping wet loins.
My prick stayed hot and solid in her pussy as we both finally came down from our pleasure high, and back into our bodies to share the afterglow of orgasm together. I finally eased my prick out of her as it softened and became very sensitive to her still throbbing pussy. I gently lifted Dawn up onto the bed and stretched out beside her to take her into my arms and kiss her hungry mouth tenderly. We lay with our arms around each other for ages as we regained our breath and allowed our pulses to return to somewhere near normal. I kissed her hot face as we slowly cooled down, and finally I pulled the quilt over us as we drifted into a very deep and satisfied sleep.