Crossword Puzzle Intimacy Pt. 02

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This is a direct follow-up to part 1 and picks up immediately where it left off. I would suggest it will make little sense – and not be as enjoyable – if you’ve not read the first part.

To recap, my Mother and I had begun an intimate relationship. But, at her insistence, we’d stopped short of having penetrative (or even oral) sex. But, to alleviate my sexual frustrations, she’d suggested that I may have some luck with an attractive, 40 something, neighbour. And she’d given me some pointers on how I might achieve this. This part begins as I try to achieve that.

So, the following day, immediately after finishing work, I found myself knocking on the back door of Janet and Peter’s home. My heart was beating at a ridiculous rate and my palms were sweaty. But I was also horny and excited. Though still unclear, despite my Mum’s suggestions, on how best to “seduce” Janet. My fear was that I would just be clumsy and gauche. Or even worse vulgar and threatening. And I’d be sent packing, with a (possibly well deserved) reputation in the neighborhood of being a sex pest.

My misgivings and nerves were eased somewhat by the warm welcome I received from Janet, as soon as she opened the door.

“Jack, how lovely to see you, come on in,” she beckoned, immediately pulling me to her for a big hug as she closed the door behind us. “Thanks so much for giving me some pointers on our new computer.”

I’m bound to say that my excitement increased, whilst my resolve (and my dick) stiffened as I saw Janet and felt her embrace.

Peter had a high powered job (something in finance) and they had the largest, plushest, house in the street. He worked long hours and was often away (hence my Mother’s suggestion) whilst Janet worked part time in a local luxury car dealership. I think it was a lowly position (just enough to keep her busy and provide her with some pocket money). But she had the taste and money to look like a high ranking executive. Today, having just returned from work, she had on a crisp, cream blouse and a tight, pencil type, skirt.

Still holding me, but at arms length, Janet appraised me and appeared to like what she saw.

“Oh my goodness Jack, you look so good since you went away to college. But how did the cute little boy I used to see playing on his scooter turn into the handsome young man I see in front of me. You’re making me feel old and frail.”

“Well, I guess I have grown up, which is what all kids do,” I laughed. Then remembering my Mother’s advice about flattery, I continued, “But you don’t look old or frail, quite the opposite in fact. You look fantastic.” As I said above, she really did, so it wasn’t at all difficult to be sincere. And I sensed, quite strongly, that Janet realised my sincerity.

“Ooh Jack, you are such a charmer,” she gushed, pulling me back in for another hug. “The ladies are going to have to be careful around you. Even the old ones like me.”

As she held me tight again I briefly considered dropping my hands and cupping her (apparently very pert) buttocks. Or chancing my arm even further by leaning in for a kiss. But, at that stage, my nerve failed me. And with hindsight, that was almost certainly a good thing. Making a clumsy pass, just minutes after saying hello, would have been a mistake.

So we fired up the computer and, standing over Janet’s shoulder I took her through some of the basics. I tired very hard to concentrate on my tutorial and not be distracted by the scent and proximity of the horny MILF in front of me. I think I managed it, but only just!

After about 30 minutes Janet was, quite swiftly, picking up the rudiments of creating and renaming files and spell checking and formatting documents. And she was pretty pleased with her progress.

“Wow Jack, this isn’t as forbidding and difficult as I thought,” she opined as she twisted to look back at me with a pleased smile on her face. “You’re very good at teaching an old dog new tricks.”

“You’re a good learner and have got the hang of this quickly,” I encouraged. “But as I said earlier, you’re not old and most certainly not a dog.” I grinned.

Actually, this self-denigration and/or fishing for compliments might have been a little tiresome. But, given how hot she was – and how much I wanted to fuck her – I made sure not to let any irritation become apparent.

That said, she continued in a similar vein.

“Don’t be fooled,” she advised, “good quality foundation conceals a host of blemishes. But look at my hands and neck. That’s apparently a good indicator of age.”

So saying, she held up a hand for me to inspect. Taking it softy in my own hands I tried to display a degree of subtlety and suavity that I probably wasn’t feeling. So I gently stroked it, under the pretense of inspection.

I’m pretty sure it really wasn’t the classiest of moves. But, by my hopelessly low standards of seduction I was rather pleased with myself.

“Mmm, these look and feel soft and well manicured, most certainly not the hands Etiler Escort of an old lady,” I reported.

Then, further surprising/impressing mylsef, I pushed her head gently downward and away from me, leaning forward to examine her neck. Initially I was just inches away, from her nape. So close she could feel my breath.

“Your neck looks elegant and you smell delicious,” I murmured into an ear, “so all told I would say that your protestations about being old are completely unfounded.”

I then stopped speaking and buried my head fully onto her neck, gently nuzzling it, whilst reigning lights kisses on it.

At this stage I was acting like an experienced seducer, not the gauche, clumsy, teenage oaf, that I was. But I’m afraid that changed moments later as my excitement and arousal got the better of me.

“Oh God, you are gorgeous, please let me fuck you,” I blurted out, whist grabbing her tits (quite roughly) and almost biting her neck. And in the process completely ignoring my Mother’s excellent advice about not blundering in. And indeed her quite specific advice of not saying, “let me fuck you.”

“Whoa tiger! Hold it right there,” Janet recoiled, pushing my hands away, standing up and turning to face me.

For a few horrible moments I thought I’d completely blown it. Janet would most certainly not consent to do anything sexual with me. And much worse, she’d report me to family and neighbours (if not the police) for sexual assault.

“Oh my God, I’m so, so, sorry, I got carried away, please forgive me,” I pleaded, beside myself with shame and berating myself for my crass stupidity.

Janet, whilst breathing heavily was initially emotionless. But at least she wasn’t ranting and screaming. To my enormous relief, I also thought I could see a smile playing in the corners of her mouth. And I was right.

“Jack, what on earth has got into you?” she began. But her demeanour and tone were kindly and curious, not accusatory. “What were you thinking and hoping to achieve? Apart, of course, from “fucking me,” as you very crudely put it,” she concluded, with a shy smile.

Reasoning that honesty was the best policy I began to explain my actions. Though I was clearly planning to omit that this was, at least in part, my Mother’s suggestion. But I did heed her advice that flattery, providing it was sincere and not creepy, was almost invariably a good tactic.

“Oh Janet, I cannot begin to tell you how sorry I am. My behaviour is inexcusable. It’s just that I’ve always found you impossibly attractive. And really sexy. I’ll be honest too, my hormones are in overdrive and I misread some signals from you. Stupidly, I thought you might be attracted to me, as I am to you. Though I realise now how daft and implausible that sounds. Please, please, forgive me.”

“Oh my goodness Jack, that’s quite a lot to process,” she responded. “I do know what teenage boy’s hormones are like. Don’t forget I was once a teenage girl. And I’ve got several lusty nephews (which was an intriguing thought). So, yes, I can see how letting you kiss my neck was a sign that I might be interested. In fact,” she continued, after taking a deep breath, “I was aware that you seemed attracted to me. And, if I’m being honest, I’m flattered by that attraction. As I said a little earlier, you’ve developed into a very handsome young man.”

By now, my terror at potential repercussions was rapidly abating. Replaced by arousal and excitement at what may lay ahead. This anticipation increased significantly as Janet moved towards me, taking my head in her hands and looking deep into my eyes.

Dropping her voice she appeared about to confirm what I’d hoped I’d sensed.

“Tell me,” she asked, “have you been thinking about me often? And what have you imagined us doing. And be honest now,” she insisted, “I don’t want any secrets between us.”

I decided to take a calculated risk here and be explicit – if fact possibly even embellish – my thoughts and fantasies about Janet. My Mother seemed to have been quite correct in the value of flattery. And the importance of employing it appropriately. I reasoned that now was the right time to give full vent to my feelings for Janet.

That said, before explaining how much I thought she had a sexy arse and how desperately I wanted to fuck her, I also recalled further advice my Mother had given about complimenting her on how good she looked, but in less overtly sexual manner.

“Ok, here goes,” I began. “The first thing you should know is how stylish, chic and glamorous I’ve always thought you were. But also very, very, sexy with it.”

I could see, right away, that I was hitting the mark here. I’m certain Janet knew how she was perceived. Not just by me, but almost all the men she encountered. But it didn’t do her – or me – any harm at all to be reminded of that.

“Oh my goodness Jack,” she preened, “that’s really sweet of you to say that. I’ve always though the Fatih Escort same of your Mum (I didn’t let on that I agreed with Janet in that regard). So, with that benchmark in your own home that’s very flattering of you. But what makes you find an old lady like me sexy compared to all the young women you meet?”

“As I keep telling you,” I laughed, “you’re not an old lady. You’re slim, you’ve got great legs and an absolutely peachy bum. I love seeing you in your leggings and tight skirts. But you’ve also got a look about you that suggests an air of confidence and sexuality.”

“Oh my goodness, you really do have a high opinion of me,” she blushed, appealingly. “And I wonder what you’ve been doing, alongside these thoughts?” she pondered. Though I felt it was clear that she had a pretty good idea how I’d answer this.

“Well, in common with most young men I masturbate a lot,” I answered truthfully, though blushing now myself. “And sometimes, when I do that, I think of you and I imagine what we might do together.”

“Oh really,” she laughed, “and what is it exactly that you imagine us doing together?”

“I think you can probably guess,” I speculated, warming to my theme now. “I’d like to undress you; to see how good those legs and bum are; to kiss you all over, including your pussy. And, of course to fuck you,” I concluded with a dirty grin.

“Well Jack,” she began to respond, in a husky whisper. “you really have been a very naughty boy. But I must say I do find it strangely and inappropriately arousing to hear what you’ve been thinking of me. Masturbating next door whilst you imagine us fucking. Whoever would have imagined that?”

“I may be taking a big risk,” she went on. “But if I make a proposal, how much can I trust you to be discreet and respectful?”

“But before I do that,” she asked. “Can I confirm, are you a virgin?”

“God no,” I assured her. Then wishing to be honest and manage her expectations, I added, “actually, I’ve only slept with a few women. But I have been having regular sex these last few months with a new girlfriend in University.”

“Ok, good to know,” she responded. Though I sensed she may have been just a little disappointed.

“As I said,” she continued, “you are a very handsome young man and I must say I find myself inappropriately attracted to you.”

Closing the few inches between us she leaned in and began to kiss me. A kiss that was clearly not the affectionate kiss of an older neighbour to a younger family friend. But the type of kiss that lovers would share.

Our mouths parted and her tongue snaked out to meet mine. Following her lead I responded with enthusiasm and was soon enjoying a deep, passionate, kiss with a woman I’d lived next door to almost all my life.

Despite this wonderfully arousing kiss (and the apparent green light it signaled) I was still reluctant, given the clumsy pass I’d made moments earlier, to build on it by caressing anything other than Janet’s back. I wanted Janet to feel she was in control and could set the agenda. Not least as I felt it would signify the trust and respectfulness she had suggested was important just a few minutes ago.

That said, Janet was gyrating against me and our kiss was becoming ever more passionate. Both of which caused my dick to harden, which she took pleasure in then grinding against. Finally pausing, it appeared I’d met with her approval.

“Mmm,” she purred, literally licking her lips, “as inexperienced as you say you are, you are certainly a great kisser.” she proclaimed.

“Right, here goes,” she went on, “still holding me extremely tightly. “As I said, I’d be taking a huge risk – in fact I have already with that kiss – but would you like to make love to me? Or fuck me as you asked earlier?” she chuckled.

“Oh my God, yes please, I’d love to. Oh I really, really, want to. But only if you’re sure? And if you’re OK with that. I don’t want you to feel uncomfortable,” I gabbled on, in an almost incoherent rush.

“Whoa, slow down,” she smiled, “if you make love in that much of a hurry you’ll be no use to me,” she teased. “And on that note, to ensure I get what I want from this, here are the ground rules.”

“The first rule, and this is an irrefutable one,” she insisted, “is that you don’t breathe a word of this to anyone. If I can rely on your discretion – and you are a decent lover – then we may be able to do this more regularly. Is that clear?”

“Oh my God, yes,” I agreed immediately. “I’d never do anything to embarrass you, or my family. So I’ll keep my mouth very tightly shut.”

“Good to hear,” Janet confirmed, “but not too tightly shut. I’ll also you need to continue to be a good kisser and an enthusiastic pussy licker,” she grinned. “I hope I don’t shock you with my candour, but most of all, what I enjoy is a good hard cock. And one that can go on and on, but not be a “wham bam” type. I want you to attend to my needs as much I do to yours. Halkalı Escort Are you OK with that?”

“Yes, of course, 100%, I’ll do that. In fact I’ll do anything you want,” I jabbered in reply. Then remembering her previous comment about being in a rush, I very deliberately slowed the cadence of my speech down.

“Actually Janet, what I meant to say is yes, I’m entirely comfortable with your suggestion. And I would absolutely love to do all I can to provide you with the pleasure that I hope and expect you will provide to me.” These utterances met with a broad smile as Janet realised my intentions.

“I can certainly guarantee you a very hard cock,” I assured her, “I think you felt that moments ago as we kissed. I also promise to do my very best to ensure it’s put to the best possible use to meet your needs.” Then remembering the importance of flattery, I expanded on my thoughts. “But, given how gorgeous and sexy you are I can’t be certain that I won’t get a little “over-excited” at first. But, with someone as beautiful and sexy as you I’m also positive that I’ll be able to perform multiple times.”

“That’s exactly what I need to hear,” she confirmed. ” And yes, I did feel your cock grinding against me. And it certainly felt very hard to me. Come on, let’s go up before I change my mind.”

Pulling me by the hand we hurried upstairs as she dragged me into her chintzy, but expensively decorated, bedroom.

“Strip,” she demanded, “let’s see your physique and that cock of yours up close.”

Confident that I was in good shape and desperate to please I tore off my clothes and stood there for her to appraise. It seemed Janet liked what she saw.

“Oh yes,” she pronounced immediately, “now that’s exactly what I was hoping for.”

At that time of my life I was fit, active and trained hard. As my Mother had commented, the time in the gym was paying off. But it was my cock, not my pecs or abs, that Janet seemed most interested in. I was already half hard. Looking Janet in the eyes I gave it a few perfunctory strokes which brought it almost to full attention.

“Oh my God yes,” she hissed, “I like the look of that. A lot. Let me see you wank it. I love watching a man playing with himself. But don’t you dare come. I want you inside me when you do that.”

I was discovering that, apparently like my Mother, I had some exhibitionist tendencies. Certainly I felt comfortable in standing, stark naked, playing with myself as Janet looked on with a huge, sleazy, grin.

That said, after a few minutes, I was keen that the clothing imbalance was rectified.

“Come on,” I pleaded, “let me see you and your wonderful body in all your glory. I want to know if your bum looks as good as I’ve imagined.”

Needing no further prompting and with her eyes still focused on my cock Janet stood off the bed and seductively unbuttoned and threw off her blouse. Before reaching behind and unzipping her skirt, which she then shrugged to the floor as she stepped out of it.

Standing before me, in a clearly expensive and extremely sexy bra and panty set, she put her hands on her hips in a mock model like pose.

“How do I look?” she asked. “As good as you’d imagined?”

“Much, much, better,” I confirmed. Once more, I really didn’t have to lie. She looked sensational. “I cannot believe what a wonderful figure you’ve got.”

“Why thanks, that really is kind of you. I try and take care of myself,” she answered, clearly pleased at the recognition and compliment.

“I love that lingerie,” I commented, “but let me see you in all your glory,” I begged.

Acquiescing immediately she completed her seductive striptease and stood before me, completely nude. Slighter than my Mother, she was almost flat chested, with small, but very prominent, nipples. In those days bushes were verdant and very seldom shaved. Though Janet appeared to be years ahead of her time. Whilst not completely shaved it was very closely trimmed. I thought it was extremely erotic and my cock twitched at the sight.

Laying back on the bed, with her legs splayed, she began to emulate what I’d done and play with herself, fingering her pussy whilst gently flicking her clit.

“Christ, that’s a horny sight,” I informed her. You look as wet as I am hard.”

“I am,” she said, “I must confess I’m really turned on. Now get down there and taste my arousal.”

Having been clumsy and impatient in my attempts at seduction I wanted to demonstrate that I was able to take my time and concentrate on her pleasure. So, moving between her legs I began to slowly tease her, gently kissing the inside of her thighs before doing the same to her vulva.

“Oh my god, that’s gorgeous,” she purred, “How about you give my clit some attention too. And insert a finger or two at the same time.”

Always eager to please I did just that, doing my best to combine gentle licking of her pussy lips and clit with some more forceful fingering. As inexperienced as I was I seemed to be doing at least something right as Janet was writhing against the bed and groaning with pleasure.

I was quite prepared to have continued this and tried to bring Janet to orgasm. But she clearly had other ideas.

“That’s wonderful, but I really need to feel your cock inside me,” she let me know, as she dragged me up on top of her.

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