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100 Sex Challenges for Jenny

'18 Today – Her Virginity Must Go!' in Literotica's 'First Time' story section provides the background to this story.

This is great-aunt Robyn's list of 'sex challenges' to Jenny and her seven sisters.

* * * * *

18 year-old Jenny has been set 100 sex challenges by her Great Aunt.

'Great sex is addictive.

Great sex is a stimulant...a stimulant every girl needs...a stimulant every girl needs regularly...very regularly!

In fact, if you ever think you need to take drugs, don't! If you think you need to take drugs, it's simply because you are not having enough sex...or your sex life needs to be a lot spicier.

My wish for you, now you have lost your virginity, is that you have an unusually active, an unusually rich sex life – because, as you will find, great sex involves much more than just taking a penis into your vagina. So I have set 100 challenges for you...many involving much more than just taking that penis into your vagina!

(And, at the end, I have explained why I have set these challenges for you, and why I believe you will benefit by accept these challenges.)

I hope you will accept every one of them...

And enjoy every one of them!

Just one final piece of advice – you'll soon discover some men are good in bed, and some are not...which of them are willing to be as sexually creative like you, which are not. Ditch the 'nots' as quickly as possible – life is too short to bother with there are lots of good, creative lovers just waiting to meet you.

1.The man who took your virginity is special – he'll probably be the 3rd most special man ever in your life (after your father and your husband). Cherish him. Keep in contact. And invite him inside you again on each anniversary of your defloration – at least until he marries, or you marry.

2.Set yourself some sexual goals, and then do your best to achieve them. You might aim to have sex every day...or aim to have sex with at least 50 different men...or aim to have completed every one of my suggested challenges within, for example, two years (after all, that's just one new discovery per week! – which would probably be a real challenge, even for a fit young perhaps within five years, which will also enable you to revisit those challenges that you have particularly enjoyed a number of times)...or all of these!!

3.Keep a diary. It will be something you'll love re-reading in the years to come...and you'll be able remember all of the men (even though some will probably deserve to be forgotten!) and be able to regularly re-live some of the most exciting days and evenings of your life. Then bring your diary with you to Heaven and read it to me – I won't be there plucking a harp; in my heaven I'll be meeting and 'entertaining' as many 'angels' - or devils - as I possibly can!

4.For starters, here are two very easy challenges. Let your man undress you, and then you should undress your man – but no touching, no fondling, no exploring each other until you are both completely naked. You should undress him as slowly as possible and be standing directly in front of him – and if he doesn't have a hard-on by the time you are finished, you will know it's time to ditch him!!

5.When you and your man are undressed, simply sit on his lap, legs wrapped around his back, foreheads touching, eyes closed, and savour the moment – for at least ten minutes, and preferably for much longer!

6.Buy a book on sexual techniques – something like '365 Sexual Positions'. Or, better still, buy a library of books. Study them, and then try all the things they suggest.

7.See how many of the suggested sexual positions you can achieve in one night. Then make it a challenge to progressively exceed your record – in exactly the same way as you try to better your time each time you go out for a serious run.

8.Have sex on the hour, every hour – until you can take no more! Urge him to cum each time (which, probably, he will soon find becomes difficult)...and have an alarm clock handy so you don't sleep through any of your scheduled sex sessions.

9.And use both of these challenges to compare your men. That way you'll discover who is the best (but, perhaps, not always the most satisfying) performer.

10.Have a 36-hour sex marathon – from 9pm Friday to 9am Sunday (at which time you'll feel totally fucked...but Sunday is the day of rest!). Keep a tally of the number of times he penetrates you, the number of orgasms you achieve, and the number of ejaculations he delivers. Tell him, though, the aim is basically to bring you to orgasm as many times as possible. Make sure you have your sex aids handy – for when he's just not up to it! And, then, use your tally as your benchmark to exceed on future 'long weekends'.

11.Visit a good sex shop and choose some 'marital aids'. I suggest at least a vibrator, an 'egg' vibrator, a dildo, and a nipple (and clitoral?) erector. A girl must always have these on hand because there will be times when the ideal man is not around, but you will be wishing he should have been...AND, after all, the female body has been cleverly designed so girls are able to easily (and effectively) pleasure themselves – so don't be afraid to use them as often as you feel they are needed.

12.But don't keep your sex toys just to yourself. It's fun having your man use them with you. He's guaranteed to especially love your dildo and your vibrator – especially when you point your rear-end in his direction!

13.And use your vibrator on him – up and down his penis, around his scrotum. And watch his reaction!

14.Avoid becoming a slut (and, apart from imploring you not to experiment with drugs or try smoking, this is the only 'don't' thing included on my list of challenges). Only have sex with guys you know and are entirely comfortable with. An invitation to dinner can be reciprocated with an invitation to dinner; an invitation to dinner should not mean you feel you have to reciprocate with an invitation to bed. And, under absolutely no circumstances, should you allow a guy to film or photograph you in the nude or whilst having sex, or should you send him nude or otherwise explicit photographs of yourself – no matter how much you might love or trust him. Nor should you ever agree to straddle a photocopier.

15.All the curves and inlets in your body have been designed to have your good looks. Don't hide them...display them...totally! Take every opportunity to flaunt your femininity. So spend a whole day indoors with your man, absolutely naked...and insist he be similarly undressed...and make him perform with you on your bed every time your nakedness causes him to have get erection. That will reduce his swelling (at least for a short time)!

16.Explore and inspect his body. Let him explore and inspect yours – every nook, every cranny, every mound...point out exactly where you most like him to where he likes to be touched...and then, as a finale, get out some body paint and paint one another...erotically.

17.Have him lick (and suck) you from head to toe...and insist he give additional attention to several prominent hills and several valleys (and sink holes) around your body. You will, of course, reciprocate by licking him from head to toe!

18.And take that naked body of yours outdoors. Start with a midnight skinny-dip with your man...then, soon thereafter, try it at a public beach during the day.

19.And be a tease. Go shopping without wearing panties, and wearing a short(ish) skirt or dress. Be sure you have to walk up some stairs, or take an 'up' escalator. If a few guys get a glimpse of your privates (or think they have glimpsed what you have down there) – so what! You'll have given them something to smile about that day – which is a wonderful public service to have performed.

20.Sit on a park bench to eat your lunch wearing a short skirt and no panties...and stay there until you are pretty sure that at least one man has realised what you are displaying.

21.You may find it less of a challenge to first venture out wearing a pair of crotchless panties – so buy a pair when you visit the sex shop. And, later, you can let your man make love to you whilst you are wearing them. That will be probably be a new experience for him – and one he will particularly enjoy.

22.Masturbate together. That's something you're unlikely to have done before – and, in doing so, both of you might also learn something about what turns the other person on. Just keep going at it until you orgasm and he also ejaculates.

23.Play the dominatrix and instruct him to be submissive. Get him to lick your love tunnel dry whilst you stand and he is on the floor on all fours...even find a leash, lead him around, make him beg like a dog...then reward him when he performs!

24.Put on the music, take off your clothes – it's time to try nude dancing. He'll be able to watch your boobs bounce, and you'll be able to admire how his manhood moves, as you rock n roll then dance together cheek-to-cheek.

25.Have a 'topless dinner' with your man. [For details see 'Preparing Melissa, Pt. 3' in the 'First Time' section of literotica stories]

26.Or better still, invite your best friend and her man to join you and your man for a 'topless dinner'. [see 'Preparing Melissa, Pt. 5' in the 'Exhibitionist and Voyeur' section of literotica stories]

27.Your pubic hair provides an imaginative, enticing canvas. Trim and sculpt it regularly, to excite your man – a full bush today...a neatly-trimmed landing strip on his next visit to your bed...then reverting to being a baldie on his next visit...then a heart X-shape the next time. You'll drive him insane...and he'll really appreciate visiting you regularly, just to discover what you have done to your pubes!

28.Even better, invite him to do the trimming. That is every man's dream (other than having his manhood up any, or all, of your orifices!).

29.Join the Mile-High Club. Join it on a regular, commercial flight – not on a bed at the back of a wussy Mile-High charter.

30.Learn to squirt (have a female ejaculation). You'll discover it is one of most satisfying things that can happen to you – think orgasms squared!

31.Be lying on your bed, naked, legs well apart when he arrives – having pleasured yourself to be sufficiently wet for what is likely to immediately happen. And have just two words of greeting: 'I'm here!'

32.Order a home delivered meal, and 10 minutes before it's due to be delivered announce there's just enough time for a quickie.

33.Text him repeatedly when you know he is coming around. 'Just six hours 'til sex. Sensational'; 'Five hours 'til you're fucking me. Fabulous'; 'Four hours to foreplay. Fondling, fingering, flirting?'; 'Three hours 'til you're thrusting. Terrific'; 'Two hours 'til we're together – very close together'; 'One hour to orgasm'; '| | minutes until \ / - no until \!/ and I just can't wait a minute longer'; '5 minutes, and I'm wet and waiting...waiting for you to cum. Where are you?'

34.Have a session of noisy sex. Groan, scream, encourage one another as loudly as you can. Lots of oohs and aahs. Really loud! The more erotic you can make your lovemaking sound, the better you will feel!

35.Have a session of talking-dirty sex. Tell him he's there simply to fuck you, to violate tell him to fuck you deeper, to stop being an arsehole and drill you faster, to shoot that load of jism now, you lazy cunt ...and encourage him to call you his cute cum guzzling gutter slut, his fuckdoll, his bitch, his whore, his dog. You get the idea!

36.Have a session of rough sex – lots of pulling, nibbling, biting, scratching, thrusting. Expect to scream! Let him clip pegs on your nipples, tie your hands behind your back before he forces you to suck his cock.

37.And have a sex session in bondage. Have him tie your hands to the bedhead, and your legs splayed wide apart so you cannot impede his entry...perhaps with a gag (your panties) in your mouth and wearing a blindfold. You'll need to trust him, though, to appreciate when enough is enough.

38.Give an older man a thrill – especially if he is a married older man (and there is no reason why he should tell his wife) or perhaps an uncle. He'll know what to do, especially if he was not expecting the invitation...and if you have it off with an uncle, you'll instantly become his favourite niece! (You can always approach your uncle by saying you need to take him to bed because this is one of the 100 tasks that your great-aunt Robyn set for you. He'll understand.)

39.And help a virgin lad (or legal age) experience 'it'...and show him how 'it' should ideally happen.

40.Men have a thing about females peeing (because it's not something they normally encounter). Start by simply having a pee whilst squatting outdoors in front of your man.

41.Then go somewhere public (such as outside a public building or at a lookout) and have a pee from the top of a flight of stairs.

42.Progress to delivering golden showers – squatting right above his face and peeing as hard as you can.

43.Then get dirty. Get him to pee all over you and, in return, you pee all over him. Then showering together will provide you both with the chance to receive full body massages – and who knows where that will lead!

44.And have an even more refined version of getting dirty. Once you have learned how to squirt, ejaculate all over him and have him, in return, ejaculate all over you.

45.Take a drive to the country just to have sex. You might book a motel room in advance, telling the receptionist you will need to be in by 12 and out by 4 – and he'll then need to be in you by 12 and out by 4!

46.Have sex under a bush in a public park – preferably at a time when strangers might be walking past.

47.Get and give some love bites – where they can be seen by others. And, to show you are in love, make sure you display a series of them in different spots on your body over a number of weeks.

48.Spend a night watching porn together...and be prepared to hit the pause button to simulate what you have just seen whenever a particularly sexy scene is screened.

49.Become his sex slave for the night, agreeing to do whatever he demands.

50.And, naturally, have him become your sex slave for the night. It's likely you'll have a completely different set of demands to those that he has!

51.Visit a strip club (with him) – purely as an education.

52.Perform a striptease – slowly, sensuously, with twirling of bras and tossing your panties to him, with musical accompaniment (perhaps 'Hey Big Spender' imploring him to 'spend a little time with me'). But practice it first.

53.Have him perform a striptease – slowly, sensuously...

54.Playful discipline is a wonderful prelude to great sex, so incorporate some occasional 'discipline' into your life. Start by having him bend you over his knee...perhaps then pulling your panties down...but, whenever you can, don't organise your 'discipline' in advance – so let him playfully 'discipline' you for something you have done (or haven't done) when you're not expecting it!

55.Graduate to being instructed to go to your room and 'assume the position' – panties down, touching your toes. If you are wearing a skirt, he can then lift it up and over your head before administering your punishment. If he makes you wait a while before he enters the room, you'll benefit from the anticipation! And, don't forget, he'll need disciplining too!

56.The embarrassment of being disciplined in front of friends will add greatly to your pleasure – so organise with your man to make that happen on one evening when friends are visiting. You will have to agree in advance whether it's to be a panties-on or panties-off session.

57.And dressing up to be disciplined is a must! A school uniform, tunic hitched high, and being punished 'for wearing crotchless panties – which are not part of the uniform - to school'...or, in a French maid's uniform, perhaps.

58.Role play is always fun...and discipline role play is exceptional fun. For example, have your man summons you at lunchtime by text message to appear at the headmaster's office at 7pm for 'wearing inappropriate clothing on your school excursion', then an hour later follow this with another text 'wear the clothes you wore on the school excursion', then an hour later 'expect to receive a lot more than a detention', etc. And, when you arrive, he'll mete out an imaginative punishment to you. Then next time it will be your turn to summons him to the headmistress's office!

59.Buy some Ben Wa balls and insert them into your vagina before you get your spanking – their pleasurable vibration will balance whatever pain you experience!

60.You were given three major orifices in which to be pleasured and from which to give pleasure. Discover how to use them all to their maximum - to receive and to give.

61.Let's start with oral sex. A blow job should not be a 'job' – it should be something exciting and stimulating. And something that both of you can have – so get into a 69 position and start simultaneously licking, sucking, swallowing one another.

62.Then turn this into a challenging game – the winner being the person who is able to get their partner to cum or orgasm first.

63.Then try oral in the dark. In a completely black room, or wearing good blindfolds. You will tease him, he will tease you!

64.He'll like trying to lick and suck strawberries and cream from your vagina; you'll love having chocolate sauce drizzling from his manhood into your mouth. I guarantee you will not be able to resist sucking the last of that chocolate off...but you may end up getting a bonus mouthful of 'cream'!

65.When he arrives one day, immediately unzipper his pants, pull them down and give him an enthusiastic blow job. Don't say anything...just give him the surprise of his life...and expect the same treatment from him at some future date.

66.Discover numerous other 'blow job' techniques from the internet: gently 'bite' his shaft as he withdraws it from your mouth and follow this with a good tonguing; suck an iceblock immediately before sucking his manhood and discover how that affects him; just tap your tongue on the hole at the tip of his penis head; learn to give a Plumber's Blow Job;...

67.And, learn to deliver ultimate oral satisfaction to your man, Deep Throat.

68.There are so many positions in which to have vaginal sex and so many different times to have it, so explore them all. Set yourself some goals in advance – for example, to have sex as soon after midnight as possible on New Year's Day, on Easter Day, on Christmas Day, the Summer Solstice, the Winter Solstice + the first of each month.

69.Then try having it in different locations – in every room of your house is the obvious first.

70.In the rain (the warm shower together afterwards will be fun).

71.In the snow.

72.At a beach.

73.In front of a mirror.

74.While others are watching (or could be watching).

75.In a lift (be aware of security cameras, though – they will be recording the action!).

76.In a forest.

77.At his office.

78.In a pool (or, at the very least, beside a pool).

79.And then there is anal. If you haven't tried this yet, you'll find the hardest thing about accepting it is psychological...and, once you've tried it, you'll probably find you'll just crave for more. So read up on how to do it first time (doggie style is probably best known, but not the best way for first-timers) and buy in lots of lubricating gel.

80.Then explore the wonderful range of anal positions – with creative names such as afternoon delight, curled angel, double decker, the amazon, the hinge, the magic mountain, the rocking horse, flat-out fun, bend-over bliss...and do have fun!!

81.See how many holes in one night your man can score – of course, providing you with cum whilst inside each one.
82.And now it's time to, for once, 'be a slut'. Invite three guys around to make you airtight. You can fanaticise that they'll all be able to cum simultaneously! If you are extra adventurous, suggest that two of them bring their girlfriends to never know what will happen then!

83.Install an ABC sexboard in your bedroom (see 'Preparing Melissa Pt. 5' in the 'Exhibitionist and Voyeur' section of literotica)

84.Act out one of his sex fantasies...and have him act out one of your sex fantasies.

85.Dress for sex – which means being as sexually suggestive and imaginative as possible! Think about dressing as a sexy schoolgirl, a naughty night nurse, a French maid, Santa's little ho ho hottie, a fantasy football fanatic, a dominatrix (complete with whip), Wonder Woman, a little devil, a ride-me cowgirl, a sexy secretary, a (female) flight attendant, a Playboy bunny...your choices are almost limitless.

86.Go back to school...or seek a professional's help. Find a sex educator who will be able to broaden your sex ed. You'll benefit from whatever you learn.

87.Enjoy no-penetration sex. A good lover should be able to bring you to orgasm by just caressing your boobs and then sucking and tongue-flicking your nipples...and you (and he) have lots of other erogenous zones that can be visited.

88.Organise a ménage-a-quatre with your best girlfriend. You both bring your man, and you take her man inside you and your girlfriend takes your man inside her. Both men will love it, both girls will be excited by it – so it's a win, win, win, win occurrence. Preferably, both couples should indulge in their sex simultaneously on matresses in the same room.

89.Write a piece of erotica and submit it to You'll discover it's fun (and you can write it to fall in love with your main character).

90.Indulge in some light-hearted sexual blackmail: think Sally faking the orgasm in Katz's Delicatessen in 'When Harry Met Sally' when she wanted to prove a point. Perhaps you too could similarly fake an orgasm (maybe even in front of his mother!) if your man doesn't agree to your demand that 'if you don't..., I'll...'... or could threaten to streak...but, beware, he might call your bluff! (And, btw, you can now sit at the same table as Harry and Sally if you visit Katz's Delicatessen in Manhattan...but make sure you perfect your fake orgasm beforehand, if you decide to have one, because the staff will be thoroughly sick of very B-class imitations.)

91.Sooner or later you'll need a holiday – not a holiday from sex, but a holiday for sex – something like an Around the World in 80 Lays. So make a list of all the romantic, spectacular places you will want to visit – and plan that the sex in each will be as memorable, or more memorable, than the scenery. Then start ticking the places off your list!

92.At least once a year, say 'thank you' to yourself for being feminine, for being sexy. It's unlikely you get enough regular compliments from men 'for just looking great and giving me the pleasure of looking at a beautiful girl'...or even, to think about it, 'for giving me a fabulous experience last night' treat yourself (or, if you can, get your man to treat you to) a day 'just for you'. Perhaps buy yourself a fabulously feminine skirt, or that pair of silk pyjamas you've always wanted, perhaps a small piece of jewellery...and go out for a special lunch or a dinner at your favourite restaurant and order your favourite cocktail, your favourite dish and a decadently delicious dessert (and forget that diet for the day)...and get your hair done, have a manicure or a pedicure...have a spa or a massage...whatever will please you, whatever will thank you for the excitement and pleasure you have given others over the past year, and whatever will 'recharge your feminine batteries' for the year ahead.

93.Commit to becoming a sex-educator. If you have a son, when he is old enough, teach him how to have good sex (sadly, it's not something that young men are taught often enough)...or ask your sisters to school him. And, I similarly suggest, you should insist your husband or your brother-in-law schools your daughters. And, of course, give the kids this list of challenges as one of their 18th Birthday presents!

94.Share this list of challenges with your girlfriends – it could be the most important gift they will ever receive. And, perhaps, challenge some of them to work through the list at the same time as you do – with you and them regularly comparing how many of the challenges each of you have ticked off the list.

95.Be sexually creative, be sexually imaginative. So I've left the final few blanks for you to complete: (literotica readers are invited to add their sex-challenges suggestions in the 'post a public comment' box below, so they can be incorporated into this submission at some future time.)





100.Congratulations! But there's no stopping now – life is far too short to let any opportunity for enjoying sex pass you by! Re-read your diary and re-live the fabulous times you've had...then start these challenges again from challenge Number 1.

* * * * *

Why the challenge? Why am I hoping you will accept these challenges?

Women's lives changed irrevocably in the early 1960s when The Pill became widely available...and I decided then that I would embrace the opportunities that it presented.

And I have no regrets, having engaged in an active and very enjoyable sex life.

I'd like you to experience the same freedom, the same excitement...simply being able to do what is 'naturally female'.

So, to encourage you, I have set the 100 challenges which I hope you will accept.

You'll appreciate that not all are strictly 'sex' challenges. This is because 'sex' includes a whole range of things including having fun, being a 'tease', having the freedom to romp naked, having a complete appreciation of your body, 'misbehaving', sharing, experimenting, learning, fanaticising...and a lot, lot more.

When The Pill became available, it was greeted as 'liberation' for women. In many ways it was.

But, regrettably, I feel that women today are less 'liberated' than they were 50+ years ago. They are not 'experimenting' sexually as much as they could are now more restricted in how and what they can offer women (for example, many of the innocent, natural things that were considered [and enjoyed as] 'flirting' by both sexes 50 years ago are now being condemned as 'inappropriate behaviour' by an increasing array of self-appointed, spoilsport busybodies)...and, perhaps worst of all, women and girls (and men, too!) are allowing many of the 'women's sexual liberation' gains of 50 years ago to be eroded – when, in practice, today's women, girls (and men!) should be working actively to extend those gains even further.

So – having experienced for myself the joys that result from being sexually active, sexually 'free', sexually inquisitive – I guess I am hoping (or suggesting, or even asking) that you will become a sort of modern 'women's sexual liberationist' by firstly enjoying an unusually active sex life (and, along the way, perhaps earning a reputation for yourself of being sexually creative!) and then will join me in encouraging other women and girls to similarly become more 'sexually liberated'...and, also along the way, will offer some resistance to those who are – consciously or unconsciously – suppressing females sexually.'

challenges   jenny   100   sex   for  

Dec 4, 2018 in anal