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Lost virginity to the wrong woman

"My girfriends forty year old mother was telling me to fuck her"

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Two things had happened in 1998.  The first being I, Terry, had just turned seventeen.  The second was my parent had just retired their old caravan as it was no longer fit for the road and the cost of repairs meant a new one was financially a better solution.  They parked it up behind my dad’s old barn and workshop.  I decided that I would turn it into my own love nest.  Talk about dreamer I hadn’t even got beyond first base with my girlfriend.  Other than grope of Leslie’s tits and some snogging it was the farthest I had got.  I blame two thirds of the world’s problems, and my own, on religion.  Leslie kept telling me she was saving it for marriage.

 

It was a particularly wet horrible night and my mates had nowhere to go or keep dry, so we all split up and my best mate Den and his girlfriend Fiona came with me and Leslie to the caravan.  I had rigged up a power cable and filled the water container up and the gas was on, so we were pretty well set up.  Den had a bottle of whisky and he and Fiona started drinking.  Den had already told me that he had to go at nine because of some thing with his parents and I assumed Fiona would go with him.  Of course, God told Leslie that she had to have tea and not whisky.  I’m a sinner so as I gave Leslie her cup of tea as I took a big swig of whisky and nearly choked to death.  That caused the three off them to laugh at me and Den call me a light weight.

 

It came time for Den to split and Fiona decided that she was staying.  Now I had God and Fiona cramping my style.  After Fiona, I took another swig.  God told Leslie it was time to go with these two sinners swilling whisky and she got up to take off.  I had always liked Fiona and thought that Den had got a good catch with her.  She was by far the best-looking girl around and had what I would call the Model look.  She was sure to be snapped up for something in the fashion industry.  As I kissed and said goodbye to Leslie, Fiona was fiddling with all the lights and switches in the caravan.  Then Leslie was gone into the wet cold night.

 

Now on our own Fiona told me, “You’re not getting me in bed you know.”  That God gets everywhere.  I must admit that up until she said that I hadn’t even thought about her that way as she was my best friend’s girl.  Fiona asked if there was a TV, and I pulled the old TV from its cupboard and turned it on.  I had seen my dad set it up many times and tried to get it working.  Fiona had taken two more swigs of the whisky and was goading me on to get the TV working.  I eventually found the amplifier and switched it on.  We had a very snowy picture and I started to play with the ariel to get better reception.  I wasn’t aware that the TV would need retuning as it was last on a different transmitter, but also the barn was blocking most of the signal.  Eventually I gave up on it and sat back down with Fiona who teased me about not being able to sort it out.

 

I said we will just have to make our own entertainment.  I had meant that we had cards and scrabble amongst many other games in one of the cupboards.  It was clear that Fiona took it entirely a different way as she moved close to me and planted a kiss on my lips.  Within seconds we were snogging.  I had a pang of guilt as it was my best friend Den’s girl, but that soon melted away as the passion rose as did my cock.  I gently reached for one of Fiona’s tits.  Leslie would have pushed my hand away for at least half an hour before I could cop a feel.  No such rebuke from Fiona.  Instead, I wasn’t sure if it was an accident, but her hand landed in my lap as we locked tongues and I mauled a tit.  Still no rebuttal as I slid my hand inside her bra and felt her bare tit.  Not my first tit but certainly the best to date.  I was plump and hot and had a big stiff nipple.

 

Now I knew the hand thing was no accident as she had turned her hand up the other way and was massaging my cock through my trousers.  Fiona was the first female other than my mother to have ever touched my cock.  I was in fear of coming in my pants.  I tried to think of other things to try to prevent coming too soon.  Unfortunately, the images of Fiona touching Den flooded my head and I wondered how far they had taken things, but fortunately Fiona stopped her massaging just in time as she stood asking where the bedrooms were.  There was one fixed bedroom and the couch we were sat on was the other bed, the one I had usually slept on.

 

Fiona was quickly in the other bedroom and started to take her own blouse and bra off.  The vision of her still hangs with me today.  She was telling me to get in there with her. The bedroom that is.   With just her skirt and panties on she lay back on the bed and I had removed my jumper and shirt and joined her on the bed.  We kissed and I could feel the warmth of her tits on my chest, and it felt fantastic.  As we broke the kiss, I just knew I had to have one of her hard stiff nipples in my mouth and Fiona groaned as I fastened onto one and I rolled the nipple around in my mouth.  The good news was that my cock no longer felt like it was ready to explode.  It was still pretty damn hard though.

 

I must have been doing thing right as Fiona was groaning regularly as I swapped from one tit to the other.  I reached down to see if I could touch her pussy.  But here comes God again as she told me no.  I decided that if I was just to play with her tits I might as well make the most of it and cupped and mauled the tit I wasn’t sucking or licking.  I could feel Fiona trembling and didn’t know why.  Then suddenly she is gasping that I can touch her pussy now.  My hand went straight up her skirt and into her panties.  This was the first adult pussy that I had seen let alone touched.  I was surprised it was wet and damp and just how sensitive it was, as Fiona jumped every time I touched the top of her pussy.  I later discovered that I had found her clitoris.  It was as proud as her nipples and stood clear of her pussy lips.

 

Fiona gasped for me to lick it.  I had heard about boys licking girl’s pussies, and some of the lads talked about it being dirty, but a few others talked as if it was the best thing in the world.  I decided to find out for myself.  I was quickly between her legs and easing her panties off her legs and feet along with her shoes, just leaving her little white ankle socks.  Then I went in for the first lick.  First impressions was it was hot wet and had a kind of fishy smell, not unpleasant, just different than what I expected.  Fiona was in no mood for me to sit philosophizing and pulled me back to her pussy with both hands on the back of my head.

 

It seemed the more I licked the more Fiona groaned and the tighter she held me to her pussy.  She was also getting wetter with each lick, and it was hard to keep up with the amount of sweet tasting honey from her pussy.  Then it happened her feet were drumming on my back, and she was waving her arms and head around.  She gave an almighty gasp and went stiff, and I thought she had pissed herself by the amount of fluid that smothered my face.  Then she collapsed back on the bed all limp and I thought that I had broken her.  Her breathing was rapid and short, and her eyes were glazed over.  I didn’t know what to do and was running things through my mind like call for an ambulance or ringing Fiona’s parents.  Then her breathing started to return to normal.  I was so pleased when she opened her eyes fully and gasped, “That was great.”

 

She took several more minutes to start moving again and then said it was my turn.  I wasn’t sure what she meant, but soon found out as she ripped my shoes, socks, trousers and Y fronts off.  My cock had gone soft while I licked and played in her pussy.  Fiona assured me I would be hard again shortly as she sucked my cock into her mouth.  She wasn’t wrong.  If this is what oral sex was all about, I loved it.  As I got more and more excited Fiona stopped just long enough to tell me that I wouldn’t get to fuck her.  At that moment with my cock in her mouth I didn’t care.  Then Fiona stopped again, and I was disappointed as I was getting close to coming, and not from my own wanking for once.

 

I needn’t have worried as Fiona moved into what I now know as the 69 position and told me to suck.  She had no need to tell me as I was already there and snaking my tongue through her pussy lips to her clitoris again.  Then it happened.  I came.  I remember gasping and then the sensation all men know as it is beyond your control as the cum just shoots out.  Spurt after spurt, five in total and then a dribble.  Fiona sucked it all into her mouth and then swallowed my load.

 

I now had this glow in me, but I also felt cold and sweaty.  Fiona was now the same way round on the bed as me and pulled the covers over us and we lay in each other’s arms.  Fiona was the first to move and break the spell telling me just how much she had enjoyed that.  It seemed the right thing to do and I kissed her.  It wasn’t like the wild kisses earlier, this was a loving caring kiss and I though that Fiona felt the same as I was feeling.  Much later we both dressed, and I walked Fiona home.  It was lucky that the rain had stopped, and I cuddled her to me as we walked along.  At the end of her road, we stopped and had a snog.  Fiona told me that this couldn’t happen again as she was with Den.  I was devastated as she walked away and went in doors.  My first sex, even if it was only oral and she had dumped me already.

 

Going back to Leslie and barely copping a handful of tits was no match for what I had now experienced.  I think Leslie sensed that I was getting ready to dump her and one evening I was allowed to bare and kiss and lick her tits.  I think she thought that would keep me interested.  Little did she know just how far I had been with one of her friends.  She stopped me way short of touching her pussy.  I had heard that Den and Fiona were also struggling with each other over something.

 

It was another wet night a few weeks later and the four of us headed for the caravan.  Once inside, almost immediately Fiona and Den were arguing.  The truth came out that Den had made love, not to Fiona but to another girl we knew.  The row was pretty heated, and Fiona shouted at Den to get out and go, and she didn’t want to see him again.  Fiona and Leslie huddled together in the corner of the couch.  Fiona was obviously upset as Den stormed off.  Trying to be the gentleman I offered to walk Fiona home.  Fiona said yes and the three of us headed towards Fiona’s house. To get to Fiona’s house we pass Leslie’s house and she decided that the night was ruined, and she would go home as well.  At Leslie’s house I got a quick peck on the cheek, and she went in doors.

 

Fiona and I continued on towards her house.  Then she suddenly stopped and asked could we talk.  I told her of course we could, and she asked could we go back to the caravan.  Again, I told her yes and we turned around and started to walk back to the caravan.  We were hardly halfway back when the heavens opened, and although we ran the rest of the way we were soaked.  Fiona said we needed to strip off and dry our clothes.  I put our clothes in the shower with a fan heater.  Both of us were shivering and decided to get under the covers on the bed just to warm up.

 

I was laid on my back and Fiona snuggled up to me to get warm.  She was telling me that she was so mad with Den, especially as she had decided to allow him to go all the way with her the next opportunity that they had, and then he went and cheated on her.  I was telling her how sorry I was and had no idea that Den was seeing anyone else let alone making out with them.  Secretly inside I was pleased that Fiona was still technically a virgin.  There was still hope for me.   I still didn’t know how far Den had been with Fiona, but he hadn’t scored a home run.  As we lay together Fiona reached out and held my still soft cock through my underpants.  Some how it didn’t feel sexual just friendly that she was holding my cock and I gave her a kiss on her forehead.  Fiona snuggled up closer to me and we laid cuddling and talking.

 

It was some time later that I could smell something getting hot and ran to see if our clothes were on fire.  Luckily, I was in time they were just hot.  Fiona laughed at me stood there in my socks and underpants.  My clothes were almost dry, and Fiona’s were dry. We both dressed and I walked her home again.  At the end of her street, I was again snogging with her, and she told me that she had very much enjoyed being with me, and that I hadn’t tried it on with her.  I joked that it wasn’t the right time, but the next time might be and gave her a playful slap on her arse. Then Fiona walked the rest of the way to her front door, turned and blew me a kiss.  I went home feeling extremely happy.

 

Den tried to make things up with Fiona and my relationship was going the same way with Leslie, down the tubes.  It was about a fortnight later and both Fiona and I were almost free agents.  Neither had finalized things with their partner, but the writing was now firmly on the wall.  I was hardly seeing Leslie at all and knew that I had to officially end things if I wanted to be with Fiona.  I was sat in the caravan watching the TV that I had managed to sort out when the door flung open and in stepped Jean.  Jean is Leslie’s mother and before I could say a word, she was tearing into be over her daughter and how upset she was.  She had no reason to be upset with me as I had barely talked to Leslie in the last week let alone do something wrong.  As much as I tried to speak, I couldn’t get a word in.

 

Then she produced a packet of condoms and the stream of insults seemed to increase.  I knew the condoms weren’t mine, the only packet I had ever bought were still unopened in my pocket, so now I was wondering where she had found them and under what circumstances.  Had Leslie been cheating on me all along, and had she given it away and not to me.  Then Jean was rambling on about tits.  In thinking about other things, I had lost the thread of what Jean was on about and I repeated the word tits.   “So you want tits do you?” she snapped and with that she was unbuttoning her bouse and then it was off and her bra was following it to the floor. It seemed so bazar what was happening.   A large pair of tits were hanging and now swinging in the breeze.  They were far larger than any I had seen before.

 

“This what you want?” she snapped.  I couldn’t talk and just nodded to say yes.  I think Jean took a swing at me and I ducked, she fell forward and as I sat back up from ducking her tits landed fair and square in my face.  I suddenly had my arms around her back as if in an embrace, but I was trying to contain the situation.  I suddenly realized that I was between the biggest tits I had ever seen, and it would be a shame not to enjoy them.  Jean went to pull back and I wasn’t sure if it was a survivalist reaction or what, but I tightened my grip on her holding her to me.  I could hear her calling me a little pervert.  My cock didn’t feel that little at that point in time as it enjoyed her tits and stood up proudly to salute them.  It didn’t help that I turned my face just a little and sucked one of her nipples into my mouth.  I think it was shock that I did that caused Jean to groan.

 

She was now trying to force me away from her tits with her hands.  The harder she pushed the tighter my grip and the harder I sucked on her nipple.  The torrent of abuse had stopped and her struggling to get free had also lessened.  In fact, it had lessened enough for me to change nipples.  Jean moaned again, and I was hoping it was because she was now enjoying it.  I was.  What seventeen-year-old hormonal lad wouldn’t like to suck on a big pair of tits belonging to a woman just turned forty and looking good on it. 

 

I lessened my grip and she started to struggle again so I immediately grasped her tighter again and sucked harder.  Jean let out a long Aaaah and stopped struggling again.  Her hands were no longer pushing me away from her tits, in fact they were holding me to them.  This time when I slackened my grip she just remained there.  One of her hands was stroking my hair as she started making mewing sounds.  I now had no grip on her, and she still remained with her tits being sucked and her hands in my hair.

 

I slid a hand down and up her thigh.  Her hand stopped me just as it went under her skirt hem.  Jean’s hand held my hand still for about five seconds and then suddenly let go.  She had allowed me to go further, and I slid my hand up higher to the hot damp area between her thighs.  A sort of soft growl escaped her lips.  I took that as approval and started to work my fingers under the material to her pussy.  I could smell the scent of her sex as I fingered her pussy, and she was making no attempt to stop me.  Even when I started to slide her sideways on the couch, she just went with it.  Eventually when she had gone over so far, I had to pull my face from between her tits.  I noticed that I had left several marks on her tits.  I wondered what her husband might make of them, although I didn’t really care at that moment.

 

Jean still didn’t resist when I got off the couch and swung her legs up onto it and parted them.  I now got a good waft of scent from her pussy.  I pulled her panties to one side and went in with my tongue.  Jean squealed and put her hands back on my head.  Then as my tongue swirled around in the heat and damp Jean started to moan.  It was now that I noticed that my cock had woken up again and was enjoying my pleasuring this older woman, and she was definitely being pleasured as she was telling me not to stop.  Not that having got this far I had any intentions of stopping.

 

Then I heard something I had never heard before.  “Fuck me.  Fuck me now.” Jean was insisting.  I continued to lick at her pussy as I struggled to remove my shoes, trousers and Y fronts.  The as I stopped licking and climbed into place Jean took hold of my cock and steered it into place and into her pussy.  In just a few minutes Jean was shaking, and her eyes were rolling.  I remembered this from my first-time licking Fiona and knew the actions which I was doing with my hips was the right thing to do.  Jean slapping my arse had me setting the right pace and then she went stiff and groaned loudly.  Something snapped in me, and I felt my cock and balls spasming as they shot load after load of cum in Jean’s pussy.

 

It was several minutes before anyone spoke or moved.  I was the first to move and untangled myself from Jean.  She was the first to speak, “I hope you didn’t do that in my daughter.  You had better not have come in my daughter.  If you made her pregnant, I’ll.”   I stopped Jean short telling her that I had never had the pleasure of her daughter as much as I had wanted to, and as for the condoms they were not mine.  Jean looked shocked as I told her that we were on the verge of breaking up and other than have a grope of her precious daughter’s tits, which by the way were not a patch on her mothers, I had never gotten any further.

 

As I told her that she was trying to straighten her rather wet panties back into place.  Then she suddenly burst out crying.  I had no idea why or what if anything I could do about it and sat next to her and put an arm around her.  Needless to say, I cupped one of her large tits as I told her it would be alright.  I could almost sense the God thing was about to happen.  Fire and brimstones or the like.  Her crying turned to sobs and I had started to massage her tit again.  Then she suddenly sat bolt upright and said that in the twenty-two years that she had been married she had never been unfaithful to her husband. 

 

I thought I should apologize, but before any words left my lips, she said that in that time her husband had never once licked her pussy.  I wasn’t sure what to say about that.  I didn’t have to say anything as she said that she wanted more.  I was all for that and dropped my other hand to her wet panties.  Jean asked was there a bed and I showed her through to the next room and she continued the strip she had started shortly after arriving.  I was quickly doing the same.  Then we were on the bed.  I tried to kiss her, but she didn’t want that.  Later I wondered was it because I had licked her pussy out earlier or did she just not want to. 

 

“Lick it,” she ordered.  As if I needed to be ordered to taste some more pussy.  I was quickly between her legs lapping at her pussy.  I was a little surprised just how much hair she had on her pubic bulge, but that didn’t stop me enjoying her pussy.  I moved around so we were in the sixty-nine position, but Jean made no moves to touch let alone suck my cock.  I didn’t care as she was climbing her way to another orgasm from the moans and groans that escaped her lips.  Then she was pushing me off and saying,” doggy, do it doggy.” I had absolutely no idea what she meant. But when I see her glistening pussy beckoning to me from behind her as she knelt on the bed, I didn’t know what doggy was, but I knew where my cock was going.

 

Jean squealed as I slammed it home followed by a groan.  Then I was away ploughing her pussy with fast frantic stabs at her pussy.  Jean was gasping for me to slow down.  When I did, I found it to be even more pleasurable and from her moans Jean agreed.  Then I could feel her legs trembling just before she went stiff and then seconds later, she collapsed onto the bed leaving me with a stiff hard cock waving around.  I needed relief and followed her down and was stabbing at her trying to get it back in.  I felt it slip in and almost immediately I was coming again.  Jean was again groaning.  I lay on top of her several minutes before I pulled out and went to move away.  It was now that I saw her bum hole was gaping open and there was some of my cum in it.

 

I had just had my first taste of anal intercourse and hadn’t known it.  Jean just lay there for a while.  I was expecting God’s thunder and lightning to land on me any minute for sodomy.  It never came.  Jean rolled over and I told her I was sorry for fucking her arse, but I hadn’t meant to.  Jean said not to worry and that it felt strange and a little uncomfortable at first, but also somehow nice.  She cuddled me to her, and my face was back where it started between her tits.

 

As we lay there Jean asked me was I sure I knew nothing about the condoms.  I again assured her that other than tits I hadn’t touched her daughter.  Eventually we both got up and dressed.  Jean told me that I could never tell anyone about what had happened between us.  I asked could I see her again.  She replied what did I think she was, and that she was a happily married woman.  I guessed not quite so happily after receiving oral sex and having her arse penetrated.  I did promise and she left looking much happier than when she arrived.  I discovered that cum had seeped from Jean’s arse and there was now a brown mark on the bed where she had laid.  I had to sneak the bedding in doors and wash and dry them in case I was lucky enough to need them again.

 

I did get to use them again until a few weeks later when I took Fiona’s virginity.  Reflecting back over those exciting and often frustrating days I had thought that when I lost my virginity it would be with Fiona and not Leslie’s mother Jean.  I don’t regret it, it was just what it was.  Fiona knows that it wasn’t with her that I lost my virginity and probably thinks it was with Leslie.  I never saw Jean again, well not biblically.  As for Leslie I have no idea whose condoms they were or if she had used any of them, but six months later she was heavy with child and went on to have a further three.  None of them mine I might add.

 

I married Fiona and we had two lovely children and now have seven beautiful grandchildren.  We still laugh about our time in that old caravan.  We loved it so much we recently bough a brand new to make new memories in. 

Published 
Written by Terry

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