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This is the story of how 19 year old Ryan finally lost his virginity (fm:older women/men, 4662 words)

Author: pluto
Added: Oct 06 2024Views / Reads: 3390 / 2810 [83%]Story vote: 9.82 (38 votes)
Ryan was in love and in lust with his girlfriend Charlotte but. despite all his efforts he was still a virgin. Then Ryan went on holiday with Charlotte and her mom.Would he finally lose his virginity to Charlotte or would something unexpected happen?
 


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December holidays, and she says I can ask you if want to come with" said Charlotte out the blue one day. It was a no-brainer "Yes" for me and I hoped the romantic beach setting would finally break her resistance. I packed a whole box of 12 condoms just in case.

When we got there it was amazing, but I was disappointed to see that Charlotte and Mrs. Laurent (which is what I called Arabelle at the time), were sharing a room and I had my own room albeit with a nice big double bed. We spent the days baking in the sun on the beach and swimming in the warm Indian Ocean. We went on boat trips, to the Dolphinarium, snorkeled, ate and drank a lot and just had a typical beach holiday for a few days. I plotted how I might get to make love to Charlotte, but her mom was always around. Mrs. Laurent was a typical French woman, and nudity was not something to be ashamed of. She wore a skimpy white bikini so see through that her pubic hairs and slit were obvious, and she would whip off her top at the drop of a hat, to reveal firm pert breasts. They were so perfect I wondered if she had had a breast implant operation which Charlotte later confirmed. She said she wanted an even tan.

Anyway, the result of that is that I had a semi-permanent erection and had to constantly wrap a towel around me. There was no way I could wear my skimpy water polo costume, not with the size erections I had. Charlotte brought up that I was ogling her mother when she took off her top (Charlotte was too shy to do that) but laughed it off and I think she was quite proud to have such a hot Mom.

"I am only going out with you because I can see how hot you will be at forty" I joked. "She is 38 nearly 39" replied Charlotte with a laugh.

That night I think Charlotte was ready, I thought. Her Mom went to bed and left us in the living room. Things were getting hot and heavy, and for the first time, Charlotte let me slip the tip of my finger inside of her. She was wet and ready as she took my cock in her hand and stroked it. ‘Fuck it's big" she said "I am not sure that monster can fit inside me" she whispered, her mother in the bedroom not less than 20 feet away.

I lay her down on the couch and started putting my leg across her tummy. "Ouch" she gasped in pain. "Where is it sore?" I asked. She prodded her tummy and pushing on the right side and low down hurt incredibly. The pain made her immediately lose interest in sex and over the next hour it grew worse by the minute. Then she started to vomit, and I became really concerned. I called her mom to come and look. By now it was the middle of the night but when her doctor Mom examined her, she immediately said "Acute appendicitis" "We need to take you to hospital" she said. It took awhile to get to the local casualty and another hour to call out a surgeon. He immediately said ‘We need to perform an emergency appendectomy"

By the time he organized theatre and called out an Anesthetist and finished the operation it was 6.00 am in the morning. "Everything went well" he said, "But the appendix had burst and there was pus in the abdomen, and we need to keep her in a few days for intra-venous antibiotics."

By the time Mrs. Laurent and I got back to beach cottage it was 10.00 am the next morning and we both collapsed into our beds exhausted. We were back at the hospital that afternoon and evening and it soon became clear that Charlotte was recovering well and out of any danger. I even got a chance to slip into bed with Charlotte and hold for a while. It dawned on me that I was unlikely to lose my virginity this holiday although it was great to kiss and cuddle Charlotte in her hospital bed (private ward luckily).

The next day Mrs. Laurent said" Ryan, this has been so stressful, lets go to the beach"

Again, she lay in the sun in her skimpy white bikini lying face down "Ryan, darling unhook my top and put this suntan oil please"

Oh fuck, I felt an enormous hardon coming on and wrapped the towel around my waist and sat on the beach next to her and started applying oil to her back, avoiding her breasts bulging out the side. "That's wonderful" she said, "Don't stop It's like a massage, so relaxing". I continued to massage her back "I need my sides done too" she said. I ventured down the side massaging her body and brushing my hands against the side of her breasts. She seemed to be loving it, and I sensed a deepening of her breathing, so I got more daring, and my hands started massaging her breasts on the side. "That feels so good" she purred "don't stop". I continued to massage her. "Was she becoming aroused" I thought. "No couldn't be, she is French she thinks this is normal" I thought. "Back of my legs please" she said parting her legs still lying face down. I obeyed and applied the oil to her sexy legs and feet. "Inside of my legs" she commanded. Now my hands were rubbing between the insides of her thighs and with each circular motion I got closer to her pussy brushing it lightly every now and then. She did not flinch and to me seemed to be drifting off to sleep. After a while she said, "Thank you darling that felt so good, I will do the front" and she flipped over and started rubbing suntan oil all over the front of her body including her breasts. "Oh my God, I am going to cum in my pants" I thought, and she is not even aware how much she is arousing me.

"I am going for a swim" I croaked and headed for refuge into the sea.

When I got back erection thankfully gone, Mrs. Laurent had her top back on and arrived back with two delicious looking chocolate ice creams. We sat in the deck chair, and she seemed to want to talk. "You know my divorce has been very hard for Charlotte" she said and proceeded to confide in me how hard it had been for her, how it had dented her self-esteem, but she had recently made a decision to start living and enjoying life again. She went on about how much of a fright Charlottes operation had given her and how she appreciated my support for Charlotte and her. "She loves you" she said, ‘try not to hurt her". I know you guys have not slept together yet, she tells me everything. It will happen soon; I think she needs to go on the pill". That shocked me a bit, but I said nothing.

It was so nice to be confided in, to be trusted and I began to open up to her about my life and by the end of that day on the beach we had developed a real connection. When we reached the beach cottage I went to shower and change to go and see Charlotte and I saw Mrs. Laurent pick up a small leather-bound book start to write in it.

I quickly showered and changed and waited for her in the living room I noticed the leather-bound book and absent mindedly opened it. I soon realized it was Mrs. Laurent's diary. Every day was dated and timed and written in her extremely neat handwriting. I flicked through it and there was a lot of mundane day to day stuff about her activities.

The date of the matric dance caught my eye. "I am so glad I made Charlotte phone Ryan and ask him to her Matric dance; she never would have if I had not pushed her. She has admired him for a long time and used to drag me to watch Water Polo because he was there. When I think of it those young water polo boys have magnificent bodies and I know a lot of the mothers would go just to perv. Ryan is tall athletic muscular, lithe and all those things, but I so lost interest in sex after my divorce. I just used to observe dispassionately. The last few months I have really come a long way, and my sex drive has returned with a vengeance. I fantasize and masturbate again and when they left for the dance I imagined Ryan, the hot young stud making love to me. I actually had an orgasm fingering myself. My first orgasm in 2 years."

Wow shock and horror! I flicked forward and read about all her angst when her daughter got appendicitis.

Then this entry: "I am so relieved that Charlotte is going to be OK" It's nice to have Ryan around, he is such a boost to my ego. I know he thinks I am sexy and would like to fuck me. He gets erections all the time and thinks I don't notice, and I catch him staring at my tits and body with lust. It's so nice to know that a 19-year-old stud finds 38-year-old me sexy. He probably has testosterone driven erections all the time and finds any half attractive female sexy buts still it's flattering and boosts my confidence."

Oh my God she knows I lust after her I thought in horror.

Next entry dated today." Oh fuck, I got so randy and hot today I am like a bitch on heat. I sensed Ryan perving on my body and getting his usual erections and trying to hide them under his towel. I thought I would have some fun and ask him to rub oil on me. When he started, it felt so good and when his hands started to skirt over my tits, I felt my nipples harden and my pussy get wet. It went on for ages and I pretended to be asleep, but it was arousing me so much. When his hand was massaging my inner thighs, I got so hot I wanted him to slip his finger into my pussy right there on the beach, in front of everyone. On the one hand this is so taboo and best avoided on the other hand I am glad I am feeling things again and my interest in men has returned. Anyway, when I turned over on to my back, I was tempted to ask him to rub my tits with suntan oil. I saw him staring lustfully at me and then he rushed into the sea I think with embarrassment"

Wow, wow, wow I was rock hard again. I heard her door opening and when she saw me my eyes were glued to the sport on TV. "Let's go and see Charlotte" she said. That night at the hospital Charlotte seemed so much better and was nagging the doctor to be discharged but he said for peritonitis she needed 5 days of ivi antibiotics. I looked at my beautiful girlfriend, held her hand, kissed her and talked to her, when Mrs Laurent left us alone for a while, and I had a huge sense of guilt at the lust I felt for her sexy mother.

Driving home Mrs. Laurent said, "Let's go home and change and walk down to that little restaurant on the beach nearby." She disappeared into the shower again and when she emerged half an hour later my jaw dropped. "How do I look" she asked twirling around in the flimsy see-through dress she was in. She had no bra on, and the nipples of her perfect breasts were cheekily visible through the thin dress. She had put subtle French make-up on, and her long hair was glistening in the evening light.

"You look stunning Mrs. Laurent" I gasped. She brushed up against me and I smelled her perfume. She grabbed me by the hand and the two of us went strolling down the beach hand in hand to the restaurant. When we were seated, I got an eyeful of her cleavage. She leaned over and took my hand and said "There are two old ladies over there gossiping about us. They are wondering if we are mother and son or whether I have a toy boy. Let's get them hot under the collar" she said leaning over and kissing me passionately on the mouth. The wine flowed we laughed and talked and had such fun and when we left, we had downed 2 bottles of wine and were both slightly worse than just tipsy. Again, we walked back to the beach cottage hand in hand and when we went inside it just seemed natural that we both went into her bedroom, and she started dis-robing.

"I am a virgin" I stammered "I have never been with a woman before" I blurted out. Now totally naked she said "Oh dear we need to fix that" as she helped me out of my tee shirt and jeans, and we lay naked on the bed together. She stroked my cock and said "I am going to teach you how to pleasure a woman"

"Woman love long slow foreplay" she said "so kiss me slowly and gently "she said as her warm tongue entered my mouth. "Then" she said, "Move down and kiss my neck lightly" and I as I did that, she then guided me "Stroke my breasts gently with your hands and then when you feel my nipples harden and you know I am getting aroused move down and suck my nipple gently" Oh my God I was in heaven. I wanted to lay her on her back and ram my cock into her.

"When you feel my breathing deepen and you can sense I am getting turned on stroke my pussy, first gently on the outside and then gently slip your finger into my slit"

"Don't go near my clitoris yet, just massage inside my pussy and enjoy feeling me get wet with desire for you. Leave my clitoris alone and make me want you to touch it. Make me push it towards you finger then stroke it gently move away then come back making me want more."

"You will feel my clitoris getting hard and engorged stroke it very gently, it's very sensitive thing"

"Oh yes that's right" she said as I felt her pussy getting wetter and wetter and her clitoris start to swell. "Now" she said, "do the same thing with your tongue". I slipped my tongue between her vaginal lips and licked and tasted her but stayed away from her clitoris.

I heard her panting and gasping with desire "Oh fuck that" she said "lick my clitoris now" I obeyed and ran my tongue slowly up and down her throbbing engorged clitoris. She started panting like a steam train and gasping. "Oui oui oui" she muttered in French ‘Baise-moi" I was not sure what that meant so I just continued stroking her clit with my tongue, her legs wide apart wrapped around my head.

"Je jouis, I am cumming, yes yes yes Oui oui" I heard her croak. Her breathing subsided "Ok I have had my first orgasm" she said, "let's get that beautiful cock of yours ready to do its job." She took me in her mouth and skillfully stroked and sucked on the head of my cock and licked. Within a minute I could contain myself no longer and I ejaculated white semen spurting out of my cock and 3 or 4 convulsive spasms all over her. "I am sorry" I blurted out. "No worries the fun has just begun" she said lying in my arms stroking my testicles and kissing me. "It takes a bit of training" she said, "Next time just squeeze hard and stop stimulating yourself or tell me to stop".

Next time turned out to be 10 minutes later when I was rock hard as I lay in this beautiful older woman's arms. She stroked my rigid dick very gently probably scared she would make me ejaculate again. "Now" she said, "I am wet and turned on and I have already had one orgasm". She lay on her back and parted her legs. "Kneel in front of my pussy, hold your cock in your hand and rub my cunt with the head of your cock' "Yes like that, it feels so good" she said as I rubbed the head of my cock up and down her slit stimulating her clit again. I could feel her breathing/ "I want your cock inside me" she said "but do it slowly and gradually" The head of my rigid dick slipped inside her between her pussy lips. I started to push it in "Slowly" she said, "Your cock is huge probably the biggest one I have had, dilate me slowly let me accommodate to the size." "The key is my clitoris make sure the shaft rubs against it"

"Yes yes like that" she gasped as I slowly penetrated her pussy deeper and deeper until my cock was embedded inside her. I felt her panting and squealing with pleasure as I pounded her with engorged throbbing dick. "Oh, fuck yes" she screamed as she lay on her back impaled on my 19-year-old cock. I grabbed her arms and pinned them above her head and pounded into her. She submitted to me completely now thrusting her pelvis in time to my thrusts, my cock splitting her in half. I felt her pelvic muscles go into repeated spasms of orgasm, clamping down on my thick long swollen cock and I continued to ram myself into her. Her legs were now wrapped around my back, and she was pulling me into her enthusiastically with her legs all the while screaming "Yes, yes, yes fuck me stud"

"Oh my God" "Oui oui oui!! "Don't cum until I tell you to" she commanded. I squeezed and rammed I squeezed and rammed. It was like poking a fire, with each thrust she panted harder and screamed louder pulling me into her willing me to fill her cunt with my young fertile seed. I leaned down and as I continued to plunder her pussy I sucked on her rigid nipple. I heard her grunt I felt her spasm, I felt her pelvic muscles involuntarily clamping and squeezing my dick. I realized she was having a massive orgasm and that drove me over the edge. I could not stop it; it was like a powerful unstoppable thing as I felt my semen spurt into her. "Oh my God" she said "I can feel your hot cum filling my pussy" "Oh, fuck Ryan, you have made me feel like a woman again, a desirable sexy woman "

"Mrs. Laurent, you are the hottest woman on the planet" I groaned. "Fuck the Mrs. Laurent thing Ryan, it makes me feel old and over the hill. Call me Arabelle. Maybe one day you will call me Mom, but until then it's Arabelle."

We lay there for a few minutes my cock embedded inside her. I could feel my tick semen leaking out her a bit. There would be a telltale wet spot the next day on the sheets. She flipped over on to her left side, and I spooned her, and we both fell into a post orgasmic sleep.

At 1.00am I awoke, my cock rigid again and I eased it into her sleeping pussy from behind. It slid in easily lubricated by my copious cum already inside. She groaned half asleep and I started thrusting into her gently from behind. She lay there submissively as I fucked her from behind. ‘Is this OK" I asked. "Yes, I love it carry on, but I am exhausted so I am just going to lie here" I slowly thrust into her. I am no longer a virgin I thought jubilantly as I embedded all 9 inches of my engorged cock into her. She in turn lay there enjoying being fucked by a young stud 20 years younger than her, with way more stamina than her. Again, I pumped the contents of my testicles deep inside her, again filling her with my hot cum. I think she enjoyed it, but she did not orgasm and soon after drifted off into a deep satiated sleep.

When I awoke the next morning with my usual morning glory, she was gone. I heard her in the shower. I joined her in the shower, and she immediately saw my rigid erection. "Fuck can't you ever get enough" she said but I fondled her breasts sucked the water off her nipples and fingered her pussy and soon she was wet and hot again.

"Thanx for the lesson last night but now its my chance to give a lesson" I said as I lifted her petite frame up against the wall of the shower and inserted my penis into her accommodating vagina. No messing about I pinned her against the wall and embedded myself deep inside her. I heard her gasp and wrap her legs around me submissively as I impaled her against the wall at the same time sucking the shower water off of her now rigid nipple. Soon I had her panting and squealing with pleasure again as I pounded her hungry pussy with my demanding engorged cock. I could not get enough of this woman; she had awakened something in me. The hedonistic pleasure she gave was something I had never experienced. She too seemed to be unable to control herself as she enjoyed the sudden orgasmic sex that we had both discovered.

"Oh fuck, this is so erotic" she said as her back was trapped against the wall of the shower and this young virile stud had her impaled on his huge cock sucking her nipple and no doubt was about to fill her with his seed again. No sex for two years and she had been fucked and inseminated 3 times in a few hours by this young insatiable stud.

"Of fuck yes oui oui oui" as she orgasmed, her pussy clamped around his cock and yet again she felt his hot cum filling her. Later, Arabelle went shopping in anticipation of Charlotte returning home. I stayed behind and searched for the diary which was now well hidden at the bottom of Arabelle's suitcase. I opened it to the latest entry: I was not disappointed, there in her neat handwriting was an intimate description of her thoughts. It began ........... to be continued if enough interest

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