Thanks to Tigersman for editing...
I'm going overseas for a month so this might be the last chapter in the Kate and Jake story for a little while. Thanks to all my readers for your pleasing and constructive comments... James Marin.
Madeleine had gone home, and Kate to work, leaving Jake and Cassie alone in the house.
"Would you like to go to my room, or stay out here?" asked Jake.
"I think the lounge room would be nice," replied Cassie, taking him by the hand, and gently leading him out of the kitchen.
When they reached the couch he stopped, and turned her towards him. Taking her in his arms he kissed her, while feeling her slender body through her robe. She responded dreamily and they stood there kissing, softly caressing each other's clothed bodies for a few minutes.
Eventually, he said, "You've had three quite different experiences today, little one... anything you'd particularly like to do now, other than just making love in the usual way?"
"Hmm," she mused. "Can I choose anything at all?"
"Absolutely," he replied.
"Okay," she said with a grin, "then I'd like to do two things. First, I'd like to take the lead for the first time in my life, like we started to do earlier on before those two lesbians jumped me."
He grinned at her joke and she smiled back at him. He then asked, "...and the second thing?"
"I'd love to find out what you and Maddy were doing with those ropes and things you had hanging from the ceiling in your room the other day."
"Would you now?" he asked rhetorically as he smiled and kissed her on the forehead. "All right. You sit down and I'll go fetch the 'ropes and things'. Better to get things organised now, rather than interrupt play later on."
She sat on the couch and he went off to his room, returning a few moments later with a cardboard box under one arm, and holding a large G-clamp in his other hand. As he deposited them on the table she asked, with wide eyes:
"What's that big clamp thing for?"
"You'll see" he replied. "I think I might set it up now, rather than have to stop in the middle of things. He grabbed a couple of ropes out of the box, a chair, and the clamp, and in a couple of minutes had the clamp firmly attached to a ceiling beam, with the ropes threaded through it, and dangling downwards. He then went back to the box, fetched a couple of fur-lined, leather, wrist cuffs, and attached each to a tail of a rope. "There!" he said. "That'll do for now. Look familiar?" he asked her.
"Pretty much like it was in your room that day. What do you do with it?"
"You'll find out soon enough," he replied. "Now, shall we start with what you want to do first, and after that, I'll show you what the ropes and clamp are for."
"Okay," she said with an ear-to-ear grin. "You sit on the couch like you did earlier on, and please don't do anything – let me do all the work... for a change."
He grinned and sat on the couch as requested. She knelt before him, parted his knees, and then shuffled forward so she was kneeling between them. She then undid the tie on his robe and parted the lapels. She looked at his cock in admiration as it lay in all its long, slack glory on the cushion between his upper thighs. She had come to love this part of him and, on this occasion, she was glad that it wasn't already hard, as it often was when he undressed. She wanted to be sure she was the one who aroused him, and also wanted the thrill of using her womanly wiles to take him from limp to erect. She picked it up with one hand and marvelled at the softness of it as she turned it this way and that to examine it from all angles. She then brought her other hand to bear, massaging it for a moment with both hands, and then using one hand to weigh his balls, while gently stretching and stroking his cock with the other. She felt a thrill and a little tingle run through her when she felt him stiffening in her gentle grip.
She then lowered her head as she raised his cock with her hand. He flopped his head back against the headrest of the couch, closed his eyes, and was transported to sensual heaven as his dainty little girl fellated him for the first time on her own initiative... and she was doing it s-o-o-o well that it prompted him to wonder if Maddy or Kate had given her any words of advice.
When he was rock hard she said, "I don't want to spoil what you have in store for me with the ropes, but I'd like to sit on your cock for a moment, if that's okay with you?"
"Of course it is," he replied with a grin. "In fact, it's the predominant wish of my heart at this very moment."
She smiled shyly as she stood, unfastened her belt, and let her robe slide to the floor. She then knelt on the couch, knees on either side of his hips, and, taking his cock in one hand, gently lowered herself onto it. Once the head was safely inside and there was no danger of it sliding off in this direction or that, she let go of it and placed her arms around his neck. She looked into his eyes as she slowly impaled herself on him.
He was fascinated watching her facial expressions and wide-eyed amazement as she (and he) felt him stretching her well lubricated, but very tight, love tunnel open... and then... he was all the way in and their pubic bones were in juxtaposition! She looked amazed all over again, and said:
"I can't believe I fitted you all in," and then with a cheeky smile added, "...but I did! Are you impressed?"
"I am," he replied, with a wiggle of his hips which made her gasp.
She kept smiling as she raised and lowered her bottom a few times to fuck his cock. He grabbed her to him, clutched her tight, and started flexing his hips to rapidly drive vertically in and out of her.
"Oh, Jake, that's so wonderful!" she managed to say, and then as he slowed down she said, "It felt wonderful while I was riding you, feeling you move inside me, but when you hold me still and pound me from underneath it is so stimulating! - want to keep doing it? I think I'll come if you do."
"I'd love to keep doing it," he replied, "and I have no doubt I'd come too, if we do... or ... we could go over to the ropes and I'll show you what we do with them. I think we'll both come over there too, but I might not be able to come here on the couch, and then over there as well – so, what do you say?"
She grinned and said, "Let's do it! I'm dying to find out what the ropes are for." She rose and fell on him three more times, enjoying the feeling of him stretching her, before climbing off him, and his very erect penis.
He said, "You really need to be dressed to enjoy the whole performance." Her clothes were still in a pile on the floor from this morning's lesson, and he said, "Just put your shorts and blouse on – don't worry about undies."
"Curiouser and curiouser," she said, quoting Alice, as she pulled on her shorts, donned her blouse, and buttoned it up.
Jake, thinking she looked sexier now, scantily clad, than a moment ago, stark naked, took her by the hand and, with his erect cock leading the way, led her over to the ropes. He delved into the box for a moment and withdrew a blindfold.
"What's that for?" asked a wide eyed Cassie.
"Part of the play, but mostly so you can't eye-ball me while I'm perving on you, or doing things to you. I'm told it also makes it more exciting for the recipient, not knowing what's going to happen next. We'll put it on in a moment – for now, give me your wrists, please."
She extended her arms towards him and he fastened a fur-lined leather cuff to each wrist. The cuffs were already attached to the two ropes hanging from the clamp on the ceiling.
"Come and stand here, directly under the G-clamp," he said, and when she was in position, he pulled on the tail of each rope. Her arms jerked skywards, and he reeled in each rope until her heels started to lift off the floor. He then let out barely and inch of rope so her feet were flat on the floor, but not quite taking all of her weight. "Now the blindfold," he said and fitted it to her face and head.
"What happens now?" she asked.
"What happens now is that you don't speak unless spoken to and given permission to answer. You're my little sex slave and I'm your Master, so you will obey me immediately and without question when I give you a command, but otherwise keep still and quiet. If you really have to say something, or seek clarification of an order, you'll ask for permission to speak, and you'll call me 'Sir' for the duration of the play session – understand all of that?"
"Yes, Sir," she said with a hint of a smile.
Jake took a riding crop out of the box and gave her a short, sharp whack on her tiny bottom. It made more noise than it inflicted pain, although, despite the fact that she was wearing shorts, it did sting, and she reflexly pulled away from it, as far as her bonds would allow; and she exclaimed:
"Ouch! What was that for? I didn't speak, other than to answer your question... Sir."
"That was for smiling and not taking this seriously enough," he said, with an amused smile she could not see. This play session was developing nicely and he was pleased.
"Permission to speak, Sir," she asked, catching on quickly to the rules.
"Yes, as long as you are not going to argue with me."
"No, Sir. I was just going to ask: is this BDSM?"
"Yep!" he replied.
"Where did you learn about BDSM, Sir? From Maddy?"
He ignored the fact that she didn't ask for permission to speak, as this was an ongoing conversation. "Maddy knows a little about BDSM and has a little more experience than me, but not much. We've both learned most of what we know from mum who has been involved in what they call: The Lifestyle; for some time now. You know how she said she does get some sexual relief with men from time to time? ...well, that's mostly when she goes out for the evening to a lifestyle group, or club, she belongs to."
"Permission to say something else, Sir?"
"Yes," replied Jake, interested to hear what she had to say now, after this revelation.
"There seems to be no end to the things you mother knows about, Sir, and the experiences she has had. She is a remarkable woman and unlike any other mother I know."
"You have to remember, Cassie, that, unlike our friends' mums, she is still a young woman: only a tad over ten years older than Maddy; sixteen years older than me; and seventeen years older than you. Some guys and girls I know have sisters in that age range. Maddy and I are eternally grateful to have a coach like mum, and I hope you'll feel the same way too, in time."
"I do already," replied Cassie, "and I'm grateful too. She's rescued our relationship, her and Maddy, and I'm eternally thankful for that."
"My little slave is becoming a wee bit too talkative, methinks," said Jake. "A couple more whacks might remind her of her responsibilities. Brace yourself, grit your teeth, and take your punishment like a true slave should, with no sound, or minimal sound, coming from you – okay?"
"Yes, Sir," she replied, and promptly clamped her mouth tightly shut.
He lined up her left buttock, drew the crop back, and laid a resounding whack on it. She flinched and grunted but otherwise took it stoically. He then repeated the exercise on her right buttock, and while she jerked a little more this time, she took that well too."
"Good girl," he said as he discarded the crop. "Now let me see what we have here – let me examine my little slave... my property; my possession, whom I can do what I like with."
Cassie went to say something, but stayed herself, remembering the rules. While the whacks were not unbearable, they did sting a lot, and she didn't want any more, if they could be avoided.
"I can tell you want to say something," he said, "Tell me what's on your mind, slave."
"Nothing important, Sir," she replied, at which he stepped in and, with his hand this time, gave her four strong smacks: one on each upper thigh, just below the hemline of her shorts: and one on each buttock.
"Never say 'nothing, Sir', or 'don't worry about it', to your Master, little slave. When I ask you a question you will always answer, and answer as truthfully and frankly as you can. You are not allowed to keep anything from your Master – understand?"
"Sorry, Sir. I wanted to say that I liked what you said a moment ago."
"And, what was that, my little slave?"
"When you said I was, 'your property; your possession, whom you can do what you like with.' That was music to my heart, Sir, and I hope you always feel that way."
Jake smiled and tousled her hair. He moved closer and kissed her softly on her lips, before his own lips wandered over her face and neck. When he noticed her squirm in pleasure, he said, "Like that do you, little one?"
"Oh, yes, Sir!" she replied, and then tested her luck by asking a question of her own: "So, BDSM is not all about men spanking and flogging women then, is it Sir?"
"No, Cassie. Masters reward or punish as required. Masters enjoy dominating, and subs enjoy submitting, and usually, everyone is happy – unless you don't like to submit, that is?"
"Oh, I do, Sir," she replied. "I love submitting to you; not having to second guess what I should be doing; just serve, obey, and be happy. I never knew BDSM was anything like this, and so far, I like it."
"I'll let mum tell you all about it – she's the expert. Right now, I'm going to get back to what I started to do, and that is to examine my slave."
She was standing tall, her arms stretched skywards, wrists cuffed, and attached to the ceiling by ropes. Jake stood back a pace, and looked her up and down. She had dainty, bare feet, long thin legs which, while a tad on the skinny side, were perfectly sculptured, and her shorts were an absolute turn on for him. They were quite brief, but because she had no bottom to speak of, there were no 'cheeky' bits hanging out, as there often are with girls in short shorts; her thighs simply disappeared into the leg holes. The shorts were not tight, but not loose either – figure hugging would describe them well – and they showed of the flatness of her belly, the curvature of her hips, her tiny waist, and the suggestion of a very small bubble butt. He walked around her, taking all this in; feeling her; sometimes caressing parts of her; sometimes prodding; and talking as he did (after counselling her not to join in the conversation).
He then went down on one knee. He was glad of the blindfold because it was not a good look in the BDSM community for a Master to kneel before his sub or slave. He circled her dainty ankles with the thumb and forefinger of each hand and then gently ran his hands up the length of her legs until the sides of his thumbs gently bounced against her denim covered crotch. He practised variations of this over the next couple of minutes, varying his techniques from simply feeling her legs, to palpating, and squeezing muscle groups, always making sure he finished at the top of each leg with the heel of his thumbs gently rubbing her pelvic floor.
"Oh, Master! Permission to speak, Sir?"
"Yes, but make it brief," he replied.
"I don't think my legs will support me much longer if you keep doing that, Sir."
"Well, if you buckle at the knees, you'll just have to hang from your wrists, won't you. I want you to exercise some self-control and remain standing."
"Yes, Sir," she replied and tried to distract herself so she had some chance of obeying him.
He stood and, walking around behind her, tried to encircle her tiny waist with the thumbs and forefingers of both hands. He didn't quite manage to do so, but was amazed at the smallness of her waist, and how much of it he could hold in his hands. He then ran the palms of his hands over her denim covered buttocks, and marvelled at not only how small they were, but also how firm they were.
"Let's see what's inside," he said as he undid the top button of her shorts, and slid the zipper down a little.
He moved closer to her, his chest close to hers, and slid his hands inside the waistband at the back. In obedience to his command, she had only dressed in shorts and shirt – no undies – so she felt the palm of his hands, and fingers, on her tiny buttocks. He rubbed and palpated them for a moment, and then slid his finger down her divide until he located her tiny anus. He momentarily withdrew one hand, licked his finger, and then placed it back on her anus. He rubbed it round and round a few times, and then pressed the ball of his finger against her puckered up anal sphincter until it yielded and his finger slipped inside. She stiffened and gasped.
"You okay, little one?" he asked.
"Yes, Sir. It's just that no one has ever done that to me before, so it feels strange... but I like what you're doing now. Are we going to have anal intercourse, Sir?" she asked.
"That's not what I had in mind. I just wanted to play with you cute little ass, is all – they call it ass play, although there is a lot more to ass play than just fingering. Did you ever do anal with Pete?"
"No, Sir. He wanted to, but I said no, so this is my first experience."
"Despite the Master/slave scenario, you can say no to me too, you know. In BDSM we have what we call limits – I'll explain later. Suffice it to say, that if you really don't want to do something, no one is ever going to make you."
"I want to do whatever you want to do, my Master," she replied, and he smiled as he hugged her to him and continued with his exploration and stimulation of her back passage.
After a little while, he went around behind her and slipped his hand, not the one that had been fingering her ass, into the front of her shorts, and played with her vulva, labia, and clitoris. When she felt a finger search out and penetrate her vagina, she sighed deeply. He massaged her womanhood and then frigged her, gently at first, but more energetically as time went by, enjoying the visible and audible evidence of her arousal.
"If you get close to orgasm, you tell me," he said. "I don't want you going off prematurely."
"Yes, Sir. I'm very close, but under control – I'll tell you."
Now, standing to one side of her, he had one hand down the back of her shorts and the other down the front, and was playing her like a two-handed musical instrument: forté and crescendo one moment, to excite her; lentement and dolcé the next, to arrest her upward spiral of arousal.
"I'll come any minute now, Sir, if you keep doing that," she said, and he slowed his ministrations, and finally withdrew his hands, to an, 'Aww!' from her.
Jake then ran his hands over her body, front and back, pausing over her boobs and manually examining them through the material of her blouse. She was not entirely flat chested, just a little under-endowed for age, with pubescent twelve-to-fourteen year old boobs, but since her body also resembled that of an early teenager in many ways, they seemed in proportion to her overall figure. They certainly turned Jake on, and that had worried him for a short time... being turned on by immature figures.
As he unbuttoned her blouse he said, "I absolutely adore you boobs."
Forgetting her slave manners, she came back with, "Do you really?"
"I do," replied Jake, deciding to let her faux pas go through to the wicket-keeper this time. He'd save it up for a day when he just felt like putting her over his knee and spanking her bare bottom, but had no reason to do so (not that a Dominant really needs a reason).
"Can I ask why, Sir?" Permission to speak was sort of implied, so he let that one go too, and she continued her question: "Most guys I know prefer big ones like Maddy's, or perfect ones like your mother's."
"Who knows why something turns one person on, and not another?" he replied. "I know your boobs and body turn me on – look!" he said, indicating his stiffy, forgetting she was blindfolded.
She didn't answer... that would have been too rude for a slave, to draw attention to her master's mistake... but she couldn't suppress a giggle. She couldn't touch it either because her arms were in bondage, tied to a skyhook. Jake immediately realised his mistake and said:
"You might not be able to look, or touch, but you can feel." He slid her shorts down and instructed her to kick them off her ankles. He adjusted his height by flexing his knees, and placed his erect penis, not in her, but between her upper thighs so its topside was rubbing on her slit and clit. He then commenced 'dry fucking' her, as we used to call it in my school days of yesteryear when 'nice girls' didn't go all the way before marriage, or at least a serious commitment, but if they really loved you, they might permit dry fucking, and even enjoy it, including getting hot and bothered themselves. The dry fucking of yesteryear was usually done with the girl's pants on, but in Jake and Cassie's case it was flesh to flesh – just no penetration... yet!
After getting her all worked up again, he peeled her unbuttoned shirt off, stood on the chair, slid it up the ropes, and stored it aloft, tucked into the G-clamp. He then came back to stand in front of her. She moaned as she felt his mouth lock on to her left boob, and writhed slightly as he used his tongue, lips, and teeth to advantage in giving her sensual, physical pleasure. He experienced erotic pleasure as he felt her nipple harden and grow under his tongue.
He reached down and played with her pussy, and this, in conjunction with what he was doing to her breasts, sent her spiralling upwards, and out of control.
"Sir, I'm going to come!" she cried out.
"Quick! Stand on the chair," he said as he pulled her blindfold off and helped her up onto it. He quickly removed the cuffs and instructed her to, "Put your legs around my waist and your arms around my neck," and she obeyed with his help. This activity and momentary distraction helped prevent her premature orgasm, but she was still sky high.
He reached under her bottom, found his now very rampant member, and guided it into her – into her vagina, this time... he would leave anal experimentation to another time when things were not so urgent. With her arms around his neck, and her legs locked around his waist, he arranged his arms around her hips, hands under her almost non-existent bottom, and commenced bouncing her up and down. Sometimes he would stop bouncing her, hold her still, and use his hips to thrust upwards into her with his rampant erection.
She cried out, "Sir! I'm coming!" and as she gripped his neck hard with her arms, with her legs holding his body in a scissor grip, he could feel her convulsing in his arms. He let the most violent part of her orgasm pass and then, while she was still twitching, her walked over to the lounge room dining table, still deep inside her, and gently deposited her on it, on her back. She watched in awe as he started thrusting again, and her eyes were like saucers when he stiffened, arched his back, rolled his eyes, and came in her with a guttural roar. This triggered either an aftershock in her, or a continuation of her original orgasm, and they came together, enjoying each other's grunts, groans, muscle twitches, and throbbings, while hugging each other tightly... until they were finally spent.
"Oh, Jake, or is it still, Sir?" she asked.
"No, the play session is over and we are sweethearts again, my love."
"That was unbelievable," she said.
"For me too," he agreed, and then scooped her up in his arms, and carried her to his room.
When they were cuddled up in bed, she asked shyly, "Why does my girlish body turn you on so much, Jake? Most guys want to play with girls with a more womanly figure."
"I don't know," he replied honestly. "Every guy has his own erotic triggers. Some guys love big boobs, even the fake look – I don't. Don't get me wrong – I love Maddy's big boobs, but they are entirely natural, and fun to play with, something different, but your little titties really get me going. It's been bit of a worry for me at times."
"In what way?" she asked, very interested to see what he had to say.
"Well, before mum banned porn in this house, I used to search out videos with the tabs: skinny; slim hipped; small ass; long legs; flat belly; small tits; petite; and teen. You are all of those things, and the perfect fantasy for me."
She laughed and said, "...and you ended up with Maddy as a fuck buddy – gorgeous, yes, but the opposite of all of those things."
He chuckled and said, "Yep, but as I said before, a bit of variety is nice. I enjoy you both at differing times, for differing reasons."
"And Kate is perfect – even I lust after her to a degree," giggled Cassie.
"Yes, she is perfect, but she is my mother, so I can't think too deeply about her attributes, other than to be proud of having a mother like her, and that leaves me free to pursue the girl of my dreams – my skinny little teenager."
"Aww, Jake," she said as she snuggled into him. "Why did you say it's been a bit of a worry for you at times?"
"It's complicated," he said. "You look pretty much like you did when you were fifteen, or even younger, other than you face perhaps, which has matured a little. There are two sides to our lovemaking, Cass: one is making love to you, the person, enjoying all the love between us, and all your qualities; the other is the physical side of it, the look of you, and, at the risk of being crude, I love fucking you."
"I'm glad," she said, "but why is that a worry?"
"One day I found myself wondering if I had paedophilic tendencies. You are eighteen, but you look younger, and I wondered if all your pubescence charms and little-girl features appealed to me because I go for under-age girls."
"You've never courted an under-age girl though," she said. "It's my good fortune that I have a guy who loves me just the way I am. You're being silly."
"I know I'm not into kids... now... but it did worry me for a moment."
"What convinced you otherwise?" she asked.
"Well, one day I was having a sandwich on the lawns of the university with a girl in my class – a woman, really, mum's age, and another young woman came up and gave her a kiss and a hug. I must admit, I was a bit taken with the newcomer. She was tall – I estimated close to six feet – and was wearing tight jeans and fitting shirt. She had a great figure to my way of thinking – very much like yours, with the pubescent figure I like: small boobs; narrow hips; small bottom; long legs; and so on. I got quite a shock when my friend introduced her as her daughter. 'You must have started young', I said, to which she replied, 'Not at all. Unlike your mum, I was twenty three when I had Sarah. Contrary to her appearance, she is only twelve, you know, although nearly thirteen now'."
"So, how did that convince you that you didn't have a fetish for young girls?" she asked cheekily.
"Because, as soon as he mum told me how old she was, I saw her in a completely different light and lost all interest in her as a sexual being. As her mum said, despite appearances, she was just a kid."
"As I remember it, you started groping me when I wasn't much older than thirteen," she teased.
"Yes, but I was only fourteen, so it has always been normal and legal between us, and you were over seventeen when we went all the way. It seems I have a bit of a fetish for pubescent females, as long as they are of legal age and mature intellect."
"I'm glad," she said as she snuggled her bottom into his lap. "You make me feel really good about myself."
"Well you should," he said. "I not only love fucking you, but I also love your mind, so there!"
"Oh, Jake, that was a lovely thing to say, and I want you to know I feel exactly the same way. I love you to bits, and the sex is just the icing on the cake... talking of which, I can feel something hard pressing on my back. What would you like to do about that, huh?"
He chuckled and said, "We could make love, or just have sex... or... try something new."
She rolled over to face him, grinned, and said, "Something new sounds interesting. What did you have in mind?"
"Since you asked about it earlier on, I was wondering if you would like to try anal intercourse? We are both anal virgins, so if you aren't too grossed out by the suggestion, I could be your first, and you can be mine... but let me be quick to say you don't have to do it – no pressure – and I won't be disappointed if you say no. I've never been attracted to the idea in the past, so I don't have a hankering to do it – it's not a fetish of mine – but on the other hand, it is something neither of us have done, and it might be interesting to explore it together."
"I'd explore anything and everything with you, Jake, I love you so much. I'm also curious, so let's try it, huh? I don't know anything about it. I hope you do."
"Only what I have read. Mum's never done it, so she couldn't tell me about it, and Maddy is an anal virgin too."
"So, if we do this then we'll know more about something than Kate or Maddy! – that'll have to be a first. They are usually our teachers and coaches. Let's do it!" she said with a cheeky grin. "Where do we start?"
"From what I've read, you need lots of lube. Mum's got some very expensive stuff in a jar which is meant to be the best – much better than baby oil. It seems from what I've read and seen in videos, that it's a good idea to start off having sex, or making love, the normal way, to get me fully erect, and you very much in the mood."
"I like the sound of that," she said. "You go and fetch the lube while I go to the toilet and have a shower. I want to be squeaky clean for you."
"Okay, but you have a shower in the bathroom, while I have one in mum's ensuite, and I'll meet you in her room in a few minutes. I think it would be nice to do it in there on the big bed, and that's where the lube is, anyway."
Less than ten minutes later they were both naked on Kate's bed, and cuddling up to one another.
"I do love you, Cassie," he said, as he kissed her sweetly on her lips, while gently fingering her down below.
"And I you," she replied.
He kissed her all over her face, nibbled her ear, traced his tongue down her neck, and then settled down to work on her boobs with his mouth. She closed her eyes and moaned, and then asked:
"Do you think my boobs are getting any bigger. Kate said they would, if they were stimulated enough. Apart from what you do to me, I have been giving them a bit of massage every day, but I'm not convinced it's having much effect."
"It's not just touching your breasts that does it, Cass. You have to do this too," he said as he gave her vulva an extra rub and inserted one finger into her vagina. The breasts have to be stimulated as part of sexual arousal and orgasm, and then, from what mum says, they do respond and grow – you need some hormones to be involved, not just a massage."
"You know, I never used to masturbate, but now you've told me that, I just might," she giggled.
"So, you don't masturbate?' he asked.
"Never used to, is what I said. Since that first mind-blowing session with you – the first one here, I mean, on our second time around, not our first disaster a year ago – I have been a bit wicked and fiddled with myself as I replayed our love making sessions in my mind."
"I'm glad you've turned into a very sensual woman," he said. "So, now you have another reason to masturbate – to grow your boobs, but don't grow them too much. I like them small."
They kissed and cuddled, caressed and petted each other, until she finally said, "Jake, if you don't take me soon, I'm going to burst."
He smiled, positioned himself between her legs, and entered her. As always, she gasped as she felt his long, thickish, love rod stretching her vagina open as it slid all the way in. They looked into each other's eyes as he slowly fucked her.
"I'm getting very high," she said, "and I know if I go off it will probably bring you with me, so how do we change to this other thing we're going to try?"
"From what I've read, and seen on videos, you can do it in a number of positions: face-to-face, like we are now; or, with the girl on all fours in the doggy position; or, lying on our sides, your cute little bum in my lap; – just to mention a few."
"Can we do it face-to-face, please, so we can both see what's going on, and also so we can look at each other and talk our way through it?"
"Absolutely," he replied. "Let's put a pillow under your bottom to raise it up a little."
He pulled out of her while getting her into position, and then, picking up the jar of lube from the bedside table, he smeared it liberally on her anus, and then started working it inside with his index finger.
"That feels so good," she said, "... strange, but good – I like it."
When he felt she was well lubricated in her back passage, he reinserted his cock into her vagina and started slowly thrusting.
"That feels so good," she said, dreamily.
"I think it might be harder to push him in the other hole, so I am just bringing him back to maximum erection, and enjoying every minute of it," he said as he looked down on her teen-like body, moving in sympathy with his, and her pretty, smiling face. Eventually, he withdrew his steel-rod-like cock and smothered it with lube from the jar. "If this hurts, tell me," he said.
"I'm sure it will," she said as she looked at his erection and wondered how it was going to fit into her tightly closed little anus, "but, Jake, unless I tell you otherwise, please don't stop or hold back. I want to do this, and I'm sure, once it is all the way in, it'll be okay. I might just grizzle a bit along the way, is all."
"Good girl," he said, as he poked her puckered up little anus with the engorged tip of his cock.
He quickly realised that no amount of pushing was going to force his blunt cock-head into her tightly closed anal sphincter. "Bear down a little," he said, "as if you were going to the toilet. I've read that relaxes the muscles."
She did, and he felt her tightly closed anus give a little, but there was no way a direct thrust was going to push his cock into her. He tried a new tack, and lay his cock in her anal divide, the underside of his cock-head resting on her anus – lying across it, rather than the full frontal attack he had been trying. As he pressed down on the top of his cock-head with his thumb, he asked her to bear down again, and they were both taken by surprise when it 'popped' inside.
She gasped; he looked concerned; but she said, "Don't take it out again! Let's just rest for a moment until I get my breath back, and then take it from there."
"All right then," he said, "If you're sure you're okay?"
"I am," she said. "The discomfort's rapidly disappearing as I get used to having him in there." she avoided the use of the word 'pain'. It actually did hurt when he pressed it in and the girth of his rampant cock stretched her anal sphincter like it had never been stretched before. "Okay – it's comfortable now. Would you like to slide it in a little further? – very slowly, please."
He did, very slowly, and she reassured him it was okay even though she was flinching from time to time as he stretched her. When he was finally all the way in, up to the hilt, so to speak, he asked:
"How does it feel?"
"Strange, but not unpleasant," she replied. "I feel very full, if you know what I mean – like when you want to go to the toilet."
He reached over and picked up a vibrator that was sitting on the covers near the jar of lube, and handed it to her.
"I don't know how true it is, but I read on a forum where some women said they hate anal; some love it; some live for it; and some never want to go back to vaginal intercourse again; that if you can bring yourself to orgasm while your partner is fucking you anally, the orgasms are very intense – but most women don't have an orgasm from anal intercourse alone. So, how about masturbating with either your fingers or the vibrator while I gently move inside you?"
She smiled cheekily and said, "I'm up for that. Intense orgasms, huh?" and she proceeded to masturbate, alternating between her hand and the plastic fantastic, while Jake very carefully withdrew part of the way, and then went all the way back in again.
It was a new and wonderful experience for him. He could literally get all the way in as there was no cervix to block his progress, and it also felt good because she was very tight indeed. Truth? He soon decided he preferred the feel of vaginal intercourse, but this was new, exciting, and something he would like to revisit occasionally. It wasn't lovemaking, nor was it just sex, but the sharing of a new experience, and that, in itself, made it special. She had placed a few pillows behind her upper back so she was propped up enough to have a good view of what was happening down below, and she found it to be a very erotic sight indeed; one that complimented her fingers and the vibrator in rapidly arousing her. While Jake was slowly thrusting he was also using his fingers in her vagina, when they were not in the way of what she was doing herself, and he was getting very turned on as he watched her facial expressions, her flexing six-pack, and other signs of arousal.
"The full feeling has gone and turned into absolute pleasure," she managed to say in ragged speech. "You can thrust a little faster if you like," she said as she moved the vibrating plastic around her clitoris, while fingering herself with her other hand.
Jake did speed up, and as he saw her grimacing and jerking on the brink of orgasm, his arousal matched hers, stroke by stroke.
Finally she cried out and bucked violently as a very strong orgasm convulsed her body. He intuitively felt he didn't have to be gentle any more, and thrust faster until he came too.
Still inside her, he leant forward and they kissed and hugged in the afterglow. Finally, he slowly withdrew from her, and now the anaesthetising effects of extreme sexual arousal had ebbed away, she gasped when he finally slipped out of her and her stretched anus started to come back to its normal size.
"I don't know if you can see this," he said, pointing to her crotch.
She struggled up to a sitting position and they both looked on in awe as a little stream of white cum trickled out of her anus and onto the towel he had laid down before they started.
"Amazing!" she said. "I often get the post-coital drip after we've made love, but nothing as immediate as this."
"Bear down a bit and see if you can push a little more out," he suggested. She did, and a constant stream of his love juices came out, sometimes in a thin stream and sometimes bubbling as it went.
They lay in each other's arms talking about what they had just done.
"What you read in that forum was spot on," she said. "That would have to be one of the most intense orgasms I have ever had."
"So, you want to do it that way again, huh?" he teased.
"Yes please," she replied, "but not all the time – only occasionally. When I say best orgasm, I mean that in a technical sense, like when the object of the exercise is just to have sex and give each other an orgasm. That was more intense than any vibrator orgasm, or even a manual or oral sex orgasms, but there is no substitute for making love, which is what I want to do most of the time," she concluded with a shy grin. "But it is important to keep the spark in one's sex life, so any time you feel like a bit of BDSM or anal intercourse, just do it, and I'll love it."
"I can't believe you're the same girl I lost my virginity too," he said with a loving smile.
"...and I can't believe you're the same guy I lost my virginity too," she said, also with a loving smile.
"Hey!" she said, suddenly animated. "I can't wait to tell Maddy and Kate that we are no longer anal virgins!"
He smiled at her exuberance and said, "What if they want to find out what it is all about?"
"I'm sure they will, and if so, I expect you to do your duty and induct them into the world of anal. You have to do it, because we can't let them be hurt by some bloke who is just getting his rocks off. Also, I want to watch you do it, so you'll have to wait until we are all together, okay?"
He chuckled, kissed her, and said, "You are one in a million, Cassie, and I love you very much indeed. Okay, if Maddy wants to find out what it is all about, I can show her, and you can watch, but I think you're forgetting that Kate is my mum."
"Oh, yes," mused Cassie. "Hmm. Is anal the same as incest? I mean, the main reason for the incest laws is to prevent closely related people having children, but you can't get pregnant through anal intercourse, can you?"
"You wouldn't mind if I had sex with my own mother?" he asked, pretending to be gobsmacked.
"Not at all," she replied, "and I think you would enjoy it too, as would she."
"What makes you think and say that?" he asked.
"Well, Jake, you'd have to look a long time to find a young lady as gorgeous as Kate – any man would give his eye teeth to go to bed with her, so why wouldn't you enjoy it?"
"I might," he admitted. "She is very sexy, indeed, but she's still my mum, and she might not feel the same way."
"Rubbish!" replied Cassie. "I've seen the way she looks at you, and even when you have a hello or goodbye kiss, she puts much more into it than any other mother I know... and so do you, so there!" she said triumphantly, with a cheeky grin. "You two are made for each other, and look so good together. I'm just glad she's quite a bit older than you, and your mother – otherwise I'd have no chance."
"Tell you what," he said, "if she does say she wants to try anal, and I'm the only guy she trusts to try it with, I might reconsider, but I'm not going to put the hard word on my mother, okay?" He was warming to the idea of a full-on foursome, but also mindful of his conversation with his mum and Maddy, wherein they counselled him to keep the incest a secret from Cassie, just in case he and Cassie went their own ways one day. After all, he was only nineteen (almost) and Cassie was only just eighteen, so a lot could happen over the next few years, and a secret shared is no longer a secret. He would play it by ear, and see what the other ladies in his life decided was the best thing to do.
"Jake?" she said, "Do you think, if we cuddle for a while, you might be up to making love to me to finish the day off in the most perfect way?"
"And, you're the girl who didn't like sex, not that long ago. It seems you are insatiable now!"
"Only with you," she said.
"Okay, well let's cuddle for a while and see what comes up," he replied with a grin.
Apr 11, 2018 in anal