The Women in My Life Ch. 09 Pt. 02

It had been an eventful 8 months to Christmas! A new job; introducing a first computer system; Lynn's husband's affair; his subsequent buggering off; Lynn's despair and our subsequent discussions of how to help her to be 'hot'. This is how...

The Mature Woman - learns to become a MILF (1988 ~ 27/28)

On the Saturday before re-opening that January morning, I went in to ready the system for the Monday 'back to work'. But at 11:30, just as I was about to close down, Lynn came in! She wished me a Happy New Year then said she wanted to ask me something. There was a look of uncertainty, excitement and nervousness about her. She stood with her back to the door and said,

"All last week, after the shutdown, I thought about what you said. And I mean all week!... I would still like you to kiss me."

As I rose from the console and stepped before her, "Are you really sure?"

"I'm sure."

"Remember," I said, "that it's you who is in control. You who makes the decisions... to start... to stop. Not me, YOU. Understand?"

"Yes, I do."

We closed onto one another's lips, feeling her hot breath against my cheek and her breasts against my chest. Our tongues twined and prodded, as my hands pulled her slightly away from the door to move my arms around her back. Her arms rested high on my shoulders. I stroked along her back, feeling the line of her bra. I pulled back to look into her eyes, seeing excitement in there. I closed back in for a second kiss, feeling her breathing rapid and hot. Slowly I brought my hand around under her arms to rest at her side just before they would touch her breast. Lynn's breathing was almost feverish as I gently touched the side of her right breast with the palm of my hand. I left my hand there as I pulled back again from the kiss.

As I spoke, I gently rubbed my thumb along the side of her breast, knowing she would feel it. "You kiss really good and you've certainly made me feel hot. Now go home and think again about what's just happened and what MAY happen. Because this is Step 1!"

Then came Monday, and at the end of the working day, before I was about to leave, I went into the Computer Room where Lynn was at the console. She looked up and asked "Are you going?"

"Just checking there's nothing else you need me for."

Standing up she said, "Well yes, there is one thing. I'd like you to kiss me again."

Lynn came round to me at the door, which I pushed shut. She raised her arms to my shoulders and entered the kiss. My hands roamed around her back and to the sides of her breasts, lightly touching without actually fondling them. Late Tuesday was a repeat. And Wednesday too!

On the Thursday, after the factory left and we were in the Computer Room, Lynn stood before me and asked, "What is Step 2?"

I replied, "Step 2 is where I cup and fondle your breast. Outside your blouse only."

Taking a breath in, she said, "Maybe we..." she started then stopped.

I turned and locked the door. We kissed and soon my hands began to move around her back. Then, with my left hand, I moved round to the side of her breast. Easing back from the kiss, I looked into her eyes. No words, just a look as I moved my hand round the front of her top to cup her breast. I kissed her again and she responded eagerly. My hand gently rubbed her breast through the top and her bra. I started a gentle kneading and fondling, rolling my finger over the enlarged nipple I could feel. Lynn's breathing was faster and seemingly hotter, with all my senses telling me to push on. But I didn't. I continued to gently fondle her right breast for several minutes, before easing out of the kiss to look at her, with my hand still cupping her breast.

"That's Step 2! I think it's time for me to go home. And take a cold shower!" I said, my hand falling away from her top.

Following a night of erotic thoughts, dreams and sexual release, it was Friday lunchtime, when Lynn said, as she was exiting the Computer Room,

"Thank you, by the way, for yesterday. I have to say I really did feel... hot!"

"Just as long as it wasn't hot and bothered." I replied.

"Not at all," and she was out the door.

Lynn was due to leave early that day, 3:30ish and as she came into the Computer Room. "I'm about to leave but I wondered if a kiss was out of the question. While the staff are still in, I mean?" she whispered.

"They can't see but they may hear. So no squealing!"

"Can't promise." she replied.

So the kiss progressed as before, with me fondling her breasts from the outside of her flimsier top this time! Finally I said, "Before the natives get restless I think you should go."

"OK." she answered, then asked from the doorway. "What's Step 3?"

"My hands are under your top but over your bra!"

"OK" she said and left. I guessed I knew what would be next.

It was Monday before I was in work again, having gone back home that weekend. So once 5 o'clock arrived the kissing progressed as before. But now, after massaging her breast over her top, I moved my hand down her side and under her top to feel the flesh of her midriff. Lynn's breath was hot, almost panting in anticipation. From the flesh of her side I moved my hand up to cup her bra, underneath the top. Moving slightly I then moved my other hand under her top to massage both breasts, teasing each nipple through her bra. After several moments, I withdrew my hands and pulled out of the kiss.

"Step 3." I said, "Your breasts feel really nice, even through your bra. Just so you know, Step 4 will see my hand underneath your bra and maybe even with it undone. Or off."

The kissing and fondling resumed, her breath almost fiery against my cheek. Tuesday and Wednesday repeated the fondling under her top.

Thursday morning, I woke early and horny as hell, having to release the pent-up anticipation of sometime poking Lynn! So I went in a bit earlier than usual. The office was empty as I went into the Computer Room and was surprised to see Lynn. After a few minutes of conversation, she said "Looking forward to later!" The day seemed to drag its way to 5 o'clock.

As we were about to kiss, Lynn simply said, "Four."

Lynn had chosen a loose, more flouncy blouse than I'd seen her wear before. Fondling her over the blouse, I then slid my hand from her breast down her side to where the blouse lay over her skirt. My hand moved inside to touch the flesh of her waist and stomach, Lynn's hot and heavy breathing continuing to encourage me. Moving slowly upwards, I came to her bra and fondled her breast through it. Rolling my hand around I moved up to the top of the bra and the flesh of her breast. I rolled my finger inside from the strap, over the fullness of her breast until my finger touched her nipple. She lightly gasped.

I pulled back from the kiss but left my finger on her nipple. I asked "Sure you want me to continue?"

"Hmm hmm," she gently nodded, so I continued to kiss her. My hand moved to firmly fondle her briefly, then moved around her back to the bra strap. It was a simple two hook and eye job, which flicked open easily. Pushing my hand under the rear of her now open bra, I traced it around to the side and then put my full palm on the warm flesh of her breast. Softly rolling my hand around her breast, her bra lifted up and I fingered her already engorged nipple. My right hand now came up the other side of her blouse, to cup her left breast. Both thumbs were now similarly rolling her nipples.

Still cupping the flesh of both breasts, I pulled back from the kiss to look her again the eyes, saying "Step 4. For me, a deliciously wonderful step. Your breasts are soft, full and so enraging my passions, my face feels on fire."

"Mine too!" replied Lynn.

I resumed fondling and caressing them. We repeated it again late Friday and early Saturday. Whilst cupping her breasts and fingering her nipples, I looked into her eyes and said,

"I must warn you that Step 5 means crossing a line!" I moved my hands from her breasts to run them around her waistline, "this line! And I remind you again that from here, you must tell me to move forward to the next step or not. YOU. And ONLY if you want to."

I withdrew my hands but kissed her briefly.

"OK, yes" she answered as she redressed herself. Then she turned and said, "I'm expecting to be on my period soon, so Step 5 may have to wait anyway."

"If you want to continue at Step 4 that's fine. Remember, Step 5 is your call."

She nodded. We left. I thought about what was likely to happen next and Lynn's awareness or appreciation of what may be expected. I decided to give her some light reading!

As it turned out Monday was busy, taken up by meetings and my having to visit off site. Before I left I gave Lynn a copy of a mild erotic/porno magazine for her to read. Tuesday and Wednesday were still busy but Lynn couldn't contain herself over what she read and the pictures she saw. She said she couldn't believe some of the stories, they seemed exaggerated. I agreed that many may be, but the essence of a truth was there. She also wondered why so many women shaved their vaginas. I lied when I said so that they got better pictures! She asked if I had any other mags. I got some more and gave her them.

So it was Thursday before some normality returned. I noticed Lynn was wearing a flouncy blouse but with a camel coloured skirt that was all buttons up the front. Early afternoon, Lynn come into the Computer Room and sat next to me.

Taking a breath in she said, "I thought about what you said last time, about pausing and thinking and crossing lines. I found myself conflicted at times, both wanting to be bold and then other times feeling timid. But... I find I am excited and more physically alive that I can remember in... in I don't know how long. It may be fleeting, it may be freeing, I don't know. I do know I want to carry on this journey. Anyway, I'm off now, I have an appointment." She rose, "See you tomorrow."

Friday was hectic, work wise, as we needed to prepare for an extra job that had to be processed over the weekend. It didn't need the two of us, but she volunteered to come in anyway! There was no kissing Friday.

On Saturday morning, after starting up the system processes and checking everything was running as expected, I checked the time. It was 8:45am. By 8:50 I was looking deeply into Lynn's eyes and kissing her. My hands moved around her, up and down her back, slowly coming round her waist and up to cup her breast, fondling gently. I undid the buttons on the front of her blouse to open it. Moments later, her bra was undone, lifted over her breasts and my hands were massaging the flesh of those breasts and tickling her erect nipples. Lynn's breath was hot, fast and desirous. With both breasts in my hands and thumbs rolling round her nipples, I eased out of the kiss. "How does that feel to you?"

"Wonderful, arousing, words I can't describe. I've never... " she paused. I waited, "I don't know, I just know that right now I want to continue." And as she looked at me, she added, "to Step 5."

So we continued. I moved my right hand around her back and let my left hand fall from her breast onto her midriff, then over the top of her waistband onto her skirt to rub my palm at the top of her hip. Slowly I moved my hand across to the centre of her skirt, just under her belly button, then slid my hand down the outside of her skirt to rest over her pubic bone. I gently pressed as I eased back from the kiss to look in Lynn's eyes and rubbed the mons of her pubis. She gazed back, not in fear or trepidation but in anticipation. "Are you sure?" I asked.

She nodded.

So I resumed the kiss, kneading her pubic bone. I moved my leg to between hers which she opened wider. Pushing my fingers forward outside her skirt, I moved my hand over the skirt, so that it rested partly under her vulva. I couldn't really feel much through her skirt but I knew Lynn could feel the pressure and the touch on her most intimate part. Roaming my hand back and forth, she widened her legs more. I pushed deeper until I held my hand flat under her vagina. Alas, with her skirt and underwear in the way. Continuing for a time, I eventually stopped our kiss, my hand still between her legs.

"So that you know and can consider where this leads. Step 6 is similar to this, except that my hand will be underneath your skirt but outside your knickers." She simply nodded as I pulled my hand away.

After Saturday, I wasn't sure what to expect, though I'd imagined all sorts and climaxed a number of times at home thinking about it. Late Monday saw a repeat of Saturday, with me attempting to knead her vulva in a circular manner, though through a slightly more flimsy skirt this time. Her breathing was quick and hot. After she'd done up her bra and top, and just as she was leaving she said, "Maybe 6 next, I think."

With expectations raging in my brain, Tuesday day seemed to crawl its way to 5 o'clock. But once the system was off and running, it wasn't long before Lynn's bra was undone and her top open and I was fondling her breasts eagerly. Still kissing, I moved my hands from her breasts to under her arms, then down her side and over the skirt to her hips. With both hands I began to gently lift the sides of her skirt. Once I felt the flesh of her thighs I slipped my left hand underneath her skirt and up to the side of her knickers. My hand rested there. Lynn was breathing heavy and hot. After a moment, with my palm flat, my hand moved across the body of her knickers, to rest over her pubic bone. I could feel the coarseness of her pubic hair through the thin veil of her underwear. I gently massaged and kneaded her pubic mons before turning my hand down towards her vulva. Sensing my movement, I felt her slightly shuffle her feet, opening her legs more. Moving my hand down the outside front of her knickers, I slid my palm in between her legs to cup her vagina, albeit with her knickers between her vagina and my hand. Even so, it felt warm and moist. Through the thin layer of her knickers, I rubbed my finger along the lines of her labia from front to back to front again, touching momentarily on her clitoris. As I did, she tensed. Though I was eager to advance, I paused. Still cupping her between her legs, I pulled back from the kiss and said, "Your clitoris is highly sensitive, you're sexually aroused and your body will be craving pleasure and satisfaction."

"I don't think I've...I've..." she stuttered.

Looking at her eyes, I rolled my finger back over the knickers where her clit was. Her eyes seemed to widen. Through the soft fabric of her knickers it was easy to feel her engorged clitoris, so I gently rubbed. She breathed faster, a look of almost fear but with excitement and anticipation. Moments later she stiffened, her eyes glaring, "Oh! Urgh! Wha.." she moaned. Orgasm shuddered through her, her legs quivering. I stopped stimulating her.

As she came down from the ecstasy and looked at me, the Console suddenly chirruped for attention, breaking the moment. I put on a grimaced face and withdrew my hand to respond to it. A minute or so later, as I turned back to Lynn, she hadn't moved. Her blouse was still open and she hadn't done her bra up. I walked forwards "How rude an interruption." I said.

"I know. Where were we?", she replied.

We kissed again and I fondled her breast briefly once more before returning my hand to the outside of her knickers to cup her vulva again. I roamed my hand around, occasionally touching the inside of her legs to the side of her vagina. A few moments later I returned to the gentle rubbing of her clitoris through the thinness of her knickers. It was so easy to feel and stimulate. I continued to kiss her until her mouth started to open wider, her legs began to shake.

She broke the kiss to look again at me with wide eyes before gasping an "Oh Oh Yes Oh". I didn't stop rubbing her this time but continued. Seconds later she was shuddering again, "Joe, Joe, Oh Oh".

As I pulled my hand away from her knickers, she looked at me then just hugged me. Hard.

"Never... ever... have I felt such... such pleasure. It was just... I can't tell you how good you made me feel." She hugged me again.

"I'm glad enjoyed it." I said.

"Enjoyed it! Tomorrow seems forever away." she said back.

Lynn reset her clothes and then we left. Separately.

At home, I had multiple ejaculations at the thought of that day. And what was to come, literally.

Wednesday 5pm seemed to take a long time to arrive. By 5:10 my hand was cupping the crutch of Lynn's knickers again. By 5:15, Lynn had orgasmed twice. The touch and feel of her vulva, even through her knickers had an effect of my manhood, stiffening in my pants. But this was not its time! After her third orgasm, we separated and as she rearranged her clothing, I surreptitiously rearranged my penis!

The next day, Thursday, turned out to be Lynn's 50th birthday. I knew this because I'd sneaked a peek at the payroll data! I bought her a slightly racy card and some chocolates and gave them to her mid morning. It was then that she told me she wasn't going out that night, as her friends had organised a Friday-Sunday spa outing! I knew she had booked the Friday afternoon off.

Incensed, I said, "No, no that's not right. You're going out. With me, after work for a meal and some drinks. You can't not celebrate on your birthday."

She started to say something, but I stopped her. "No ifs or buts."

So there was no kissing after 5pm that day. I told her to go home, get changed if she wanted and I'd pick her up at 6:30. Which I did. We went to a pub/restaurant a little out in the sticks and had a nice meal. Lynn drank most of the bottle of wine. I was driving so just had one glass and some water. By 9:30 we were back at Lynn's house. She invited me in.

I sat in the living room as she put a kettle on for some tea. She came in with two cups and sat next to me. I realised she was a little tipsy! She turned to face me,

"What is Step 7?" she asked.

"My hand would be inside your underwear not outside. Or you'd have no underwear on at all." I answered.

"Seems a shame to wait until tomorrow!" she urged.

"Is that you or the drink talking?" I asked.

"It's me. The drink just helped. So..." she replied, as she leaned towards me.

I pulled her face towards me and kissed her, before gently leaning us both down on the settee. Slowly fondling her breast outside I then undid her bra to caress the warm flesh of her breasts and hardened nipples.

Soon I moved my hand down her side, over her waistband to pull up her skirt. My hand slid up the outside of her leg to the side of her knickers. Sliding my hand around to her buttocks then over the top of her panty line and inside to cup her soft but firm buttock and kneaded it. I moved my left hand back around to the side then across to palm her brush of pubic hair. Lynn's breath was hot and almost frantic. Rotating my hand I slid it down to cup her hot and wet vaginal entrance. I rubbed my finger along the sides of her vaginal lips, without poking it into her so enticing hole. Back I pulled to once again touch her clitoris. At this, she pulled back from the kiss with a look of desire, possibly lust. I rolled my finger round the prominence of her clitoris, then began a steady rubbing. I could feel her tensing, could feel her breathing quickly and see her eyes widening. Her face began to almost grimace as, closing her eyes, she shuddered and grunted in ecstasy.

I didn't stop rubbing her clit, I carried on. Moments later, yet again, she stiffened and shuddered in pleasure. I stopped but left my hand cupping her moist vulva.

"So, how do you feel?" I asked.

She breathed deeply, "Tingling all over. It was the most exciting, exquisite feeling I've ever had. I've never ever felt anything like it, so intense and oddly relieving."