By Design

By design 2

Chapter 1 should perhaps be read first for context. Introverted young man works with shy, quiet, but horny older woman. Things heat up and a new arrangement is made. Loosely based on real life events. All characters over 18 years of age.

The return

I had plenty of time to think as I jogged back to my apartment. What was I getting myself into? Here I was, mostly a nerd, who really didn't have a girlfriend at college, had a few hook-ups at college parties, too interested in sports, trying to make ends meet without a scholarship, working two jobs, and just scraping by.

Now that I was working, not much had changed, still playing sports, no girlfriend to speak of, my best friends were books, my work, and when needed, my hand. I know I had a vivid imagination and a fascination with older women, because to me, girls of my age just didn't seem to draw me into looking for a long-term relationship. Maybe it was me.

Maureen's outrageous behaviour at the office had fired up my imagination, had drawn me into a wild mind ride of possibilities, so the thought of backing off and not going back to her cottage was the furthest thing from my mind, even though she had to be thirty years my senior.

I dug my apartment key out of the change pocket in my shorts, and quickly packed a small holdall with clothes for the long weekend and, just in case, clothes for work after the weekend.

A quick change into something decently casual, a quick look around, then into my non-descript Toyota for the run back to Maureen's. I parked away from her cottage, near an open park, to avoid any embarrassment for her from prying neighbours and sauntered up to her door.

I barely had rung the doorbell when it opened and Maureen whisked me inside, throwing her arms around me and giving me a deep lip crushing kiss.

"You DID come back!" she breathed.

I held her close and let her settle, kissing the top of her head as she leaned into my chest. She had changed into a gauzy purple blouse and a flowing black skirt, with soft Chinese slippers. I stroked her back and even in casual dress I felt the outline of a bra under her blouse. I dropped my holdall on a hallway bench and cradled her face, looking into her eyes dark and round through her thick lenses.

"Of course I did -- I said I would and I have a whole weekend's worth of nibbling ahead of me." I teased her.

"Well, I made some snacks, so you better make a start on that." she teased back, taking my hand, and dragging me to the warmly lit kitchen. She served up cheese and crackers for both of us and we sat down at the small table. Her hands flittered nervously about as she reached for plates and napkins until I place a hand on her arm.

"Maureen, relax -- I'm in no rush and we have the whole weekend ahead of us." I said.

She exhaled slowly and I could see her eyes watering, so I lifted her up from her chair and set her down on my lap.

"Relax now, beautiful," I said as I kissed her cheek gently, stroking her back. She slowly began to breathe slower, and so I simply pulled a chair around next to mine and eased her into it, with our thighs rubbing up against each other.

We ate the snacks, interrupted at times with my hand wandering over her lap to squeeze her thigh or leaning over to kiss her behind her ear. Slowly a smile returned to her face and she began to relax. We chatted about mundane things in our lives, and once we had finished, I washed up for her while she made coffee.

We moved to her living room -- attractively furnished with a large television and a remarkably high-end stereo system. It was quite apparent that she favoured music over TV, probably because of her poor eyesight. I found some light classical CDs and put on a soft mix of guitar solos. She settled comfortably next to me on the couch, drawing her legs up under her, leaning into my chest and sipping on her coffee. I stroked her shoulder and kissed the top of her head.

"How are you feeling now?" I asked.

"Nervous, and I cannot quite believe this is happening!" she murmured.

"Well that makes two of us," I whispered into her ear, "so let's just ease into this."

I slowly slid my free hand across her chest and undid a couple of buttons, then began to caress her breasts under her blouse.

"You have wonderful breasts and really responsive nipples," I teased her. She squirmed and blush crept across her face. "It would make it much easier if I got rid of your bra."

"That's a little brazen!" she whispered

"And this isn't?" I responded with a gentle tweak at her stiffening nub.

She smiled and sat up, put down her coffee cup, and pulled her blouse from her skirt, turning so I could reach under the back and unfasten the restraining item. With a bit of squirming and arm twisting, she handed the offending bra to me. Her breasts were now free, sagging just a little, the hardening nipples pushing out against the silky blouse. I rubbed them through the blouse, and she groaned as they responded, hardening more and standing out against the silky blouse.

Maureen lay across my lap, stretched out, turned her head and we kissed deeply, tongues clashing as I stroked her breasts under her blouse. She gripped my hardening cock though my slacks and squeezed and stroked as she moaned her arousal. My hand moved down and over her skirt, lifting it to allow me to squeeze her thighs, and slowly move up to the apex of her sex. No girdle, no granny pants, just some silky panties.

Her moans intensified as I wormed my way up to her silk covered slit, already moist from her arousal. I gently pressed my fingers into her, being rewarded by a shortening of breath and a growl of lust from her throat as her mouth attacked mine ferociously.

"Would you like to get more comfortable?" I suggested.

After a moment's hesitation, she smiled weakly.

"This is another first for me," she whispered, "a man in my bedroom, intent something other than redecorating!"

She smiled and stood nervously, dragging me up with her and led me down a warm carpeted corridor to the master bedroom.

Like the rest of her house, Maureen's bedroom was artfully decorated, subdued, dominated by a low queen size bed with a warm pink comforter, with matching decor. The lighting was low, but I could see that it was extensive, and could be brightened substantially.

She stopped just inside the door and waited until I took her hand and led her to the bed. I sat on the edge and moved her to stand in front of me.

"Are you sure you want to do this?" I asked softly, holding her hands.

"Please be gentle with me," she whispered "I know I acted like a brazen hussy at the office, but really and truly, I'm nervous and I haven't had a man in such a long time, so I am worried I am going to be a failure, just like always."

I could tell she was nervous as the Irish lilt became more pronounced as she spoke. I took off my shirt, then added my slacks, boxers, and socks to the pile on the chair next to the bed.

"Maureen, there is nothing to be embarrassed about. You have a wonderfully full body, nothing like the bony sylph like the airheads we see out there. And, for good measure, you are horny and not afraid to take what you want."

"This is going to be a genuinely great experience for both of us. See what you are already doing to me?" I said as I stroked my already hardening cock in anticipation of taking this sexy matron.

A blush spread from her neck to her face, and I slowly drew her blouse off her shoulders, and folded it on the stack of my clothes. Unclipping the fasteners on her skirt, I lowered the zip and let the skirt fall to her ankles, stroking her thighs and cheeks covered in the plain silky pink panties she had on.

"One last little bit," I said, "are you still OK with this?"

With almost indecent haste, Maureen stripped off the panties and dropped them on the skirt.

"Yes!" she said firmly and moved her hands away to reveal her full bush of tightly curled red hair, starting low on her belly and flowing down past her slit to disappear between her thighs.

I stood up and began to run my hands all over her body, her back, breasts and ass, slowly working my way around to cup her wet pussy. I held her gaze through her thick lenses and took her hands and put them to my cock. In no time she was stroking the shaft and feeling my balls hanging low in their sac, her fingers kneading and pulling me to a harder and harder erection.

Maureen was full figured, but not, as she was so worried about, fat. She had plumpness about her hips and lower belly, her breasts were a little small, with just a little sag that belied her years. Her nipples were darker, and very pronounced, some would say, large.

I pulled her close and whispered in her ear as I moved her to the queen-sized bed.

"We'll take this slow and easy Maureen," as I pulled down the comforter and sheet, plumping the pillow for her.

"Let me help you relax," I whispered as I removed her glasses, placing them carefully on the bedside table, and began to run my hands all over her body.

Her eyes were wide, blinking at the loss of focus, and she gripped my arm.

I helped her lay down in the middle of the bed, her eyes wide and blinking. Starting at her shoulder I began to softly massage her neck, shoulders arms and then began a slow delicate slide over her breasts. She gradually relaxed, her breathing becoming more and more even, and softer. Her eyes closed.

I lay down beside her, her head resting in the crook of my elbow, and whispered "Remember, this is all about letting go and just enjoying the feeling."

I ran my hand down over her breasts, toying gently with her nipples, running my palm over the stiff nubs, and leaned over to suck at her throat, gently washing my tongue up and down her chin, over her lips, nose and eyes. Her breath was a little ragged now, and as I slid my hand lower, I could feel the ripples in her stomach as she became more and more excited.

I was laying at her side with one arm between us, and could feel her fist clenching and unclenching, her free hand was in my hair pressing me down as I moved about her breast and neck. Each time I passed over her lips she pressed me down for a kiss, her tongue rasping over mine as I pressed it deep into her throat. The prickles on her upper lip were driving me crazy each time we kissed.

I slid my hand over her bush and let my finger probe into her slit. Her juices were flowing; she was wet and ready for anything. Carefully parting her pussy lips, I slid a finger up and down her moist channel.

Turning my head slightly so that I was at right angles to her face, I widened my mouth and covered hers completely. Just as my mouth descended on hers, I drove my tongue deep, as far down to her throat as I could go, slid two fingers into her pussy, and flicked at her throbbing clit with my thumb.

She came explosively, her hips bucking up to try to drive my hand deeper into her, her stomach rippling as the waves of orgasm ripped through her. A guttural howl tore from her gut into my mouth, her free arm gripping my neck as she crushed my mouth deeper into hers. Her body continued to pulse and react, so I eased the pressure on her clit, and she fell back, her eyes closed, arms limp, and breathing hard.

I was a little worried she had passed out, so I stroked her gently as her breathing returned to normal, caressing her tits, tracing my fingers down her stomach to cup her wet throbbing pussy. She murmured something and I leaned over and kissed her softly, rubbing my cock into her thigh. Her eyes shuttered open and she smiled.

"What did you do to me, Ben? When you drove your tongue into my throat, and then you did that to my clit, my mind just exploded, and it was all I could do not to wet myself!" she whispered.

"Are you sure you are OK, Maureen?" I asked.

"Oh yes, Ben, more than OK. In fact, -more!" she whispered and gripped my cock with her free hand, "I really want to feel this inside me, please, Ben," she begged.

I smiled and kissed her, spreading her legs as I slid over her. I rubbed my cockhead up and down her wet slit, and she groaned. I eased the tip to her lips and began to press into her. She groaned, and began to hump upwards, looking for more. Very gently, I slid forward, my shaft gliding easily into her soaking cunt.

Instinctively Maureen spread her thighs and lifted them for a deeper fuck. Her heels crossed over my hips and rested in the small of my back as she began to hump upward meeting each of my thrusts with fearsome abandon.

I deliberately kept up an even soft thrusting, not hammering away at her, but rather savouring each thrust to the full, grinding our groins together at the fullest and easing almost out of her before driving back into her.

Her moans were becoming more insistent, more breathless and in what seemed to be just moments, she screamed out her bliss as she clamped my cock tight with the walls of her pussy in a gripping orgasm. It was all too much for me, and I thrust deep into her and came hard, my cum sluicing into her womb.

I collapsed to the side of her and we lay there, arms bout each other, breathing hard, her head buried in my neck as my cock began to soften and slip from her, despite her clenched pussy trying to keep me embedded in her.

We lay quietly entwined for a long time, until she began to weep softly into my chest.

"What's wrong, Maureen?" I asked, "are you hurting?"

She smiled softly, "Oh no, nothing like that at all, just overcome with emotion, you see I haven't made love like that for a very long time. Just the thought of having a man take the time to warm me up, then take me softly and then hard, overwhelmed me. It just brought a whole host of memories back."

We lay there, my arms around her, talking for a long time, before her breathing softened as she fell asleep. I drew up the covers over us and it didn't take me long before my eyes closed, and I fell asleep too, breathing in her scent.

Maureen's story

I slept poorly, mostly because of a softer bed, but more so because of a warm body spooned up against me all night. I woke to find my arm over Maureen, who had it tucked under her arm with my hand cupping a breast. It was, for me, very different from a normal night.

As I gently stroked her breast, I thought about what she had told me last night, of her domineering parents, the very closeted, and the sheltered existence she had led.

Her parents doted on her older brother, who left home early, and went on to become a priest, now working in a parish in another state. She was never close to her family, and because of her plumpness and her sight issues she endured the teasing and bullying in school, which had affected her, and led to a very solitary existence.

As soon as she graduated and turned 18, she had left home, and enrolled in an all girls' secretarial school, finishing with an administrative assistant's diploma. She joined a small construction company as a secretary and met her future fiancé when the company won a contract to build new hangars on a local air force base.

They dated, she lost her virginity to him and after a long dating period, he proposed, and she accepted. They were planning on a reasonable engagement before marriage, to build up enough savings to build a house before the wedding.

All that came to an end when he was killed in a mid-air collision during a training flight. She didn't go into detail, but I could see that she never stopped loving that man. She became very depressed and isolated, quit her job, and moved cities, where she eventually joined the company we both worked for now.

She never dated, and rarely went out. I could see that she was still very much in pain, and love, and held him close to her heart.

She began to stir, I kissed the back of her neck and she murmured in response, pushing back into me with her ass.

"Are you OK, Maureen?" I said softly into her neck.

She stretched a little, "Mmmmmm," she responded.

As I caressed her breasts and stomach, I could feel her responding, stretching and rubbing up against me.

"What would you like to do today?" I asked her.

"I'd like to say more of the same, but in truth, I am a bit tender down there. You gave me quite a workout." she whispered, "If we are going to do that more often, I'd like to go out and get some new, umm, clothes, and not granny panties."

"OK, I'll take you to the mall," I said, "but first a bit of sustenance to make sure we can survive this three-day marathon. How about I make some coffee, toast and anything else you'd like?"

I wasn't sure how she was going to react, having woken up with me there in her world, and if she was going to have second thoughts about anything, now was as good a time as any to get them into the open. I slipped out of bed and found some shorts in my holdall, hoping to be at least half decent making her some breakfast.

I was busy putting the mugs for the coffee on the table, along with batch of toast, butter and jam when she sipped into the kitchen. Dressed in a gown and her slippers, she had run a brush through her hair and found her glasses, but she did have a shy smile on her face as she came up to me, reached up and wrapped her arms around me and gave me a scorching kiss. I guessed we were going to be doing a bit more than just shopping later that day.

I held her close, ran my hands down her back and squeezed her ass, kissing and nibbling her neck.

"We'll never get to the mall if we keep on doing this," I said, and slipped my hand under her gown, finding that she was naked under the silky robe. As I caressed her breasts and slid my hand down to cup her pussy, kissing her deeply, I could feel the wetness begin to flow

"Let's eat and get going so that we can get back quicker." I whispered.

Food for thought

Maureen chatted away as we headed out to the major outlet mall some distance from her home. As we drew closer, she became a little pensive, and looked at me and with a serious expression asked

"I know I have to do something about my wardrobe, Ben, but seriously, I don't want to look foolish by getting something outrageous that makes me look like a fat old woman in a totally inappropriate outfit. What are your thoughts?"

"Maureen, I have already mentioned I love the look of a mature woman, yes, even with a bit of flesh on the bones. In all honesty, I know that you will always take a less risqué approach, but I would love to see you in something that accentuates your sexy curves."

"Be yourself but let yourself try for a look that you've never really had the courage to go for. I won't judge, trust me, but I will appreciate anything you decide on" I replied.

"To make things easier for you, I am going to find a quiet spot in the food court, grab a coffee and read the paper. Don't worry about time, I have my iPad with me, and I am loaded up with reading material. So, you won't have me to be there looking over your shoulder and making you uncomfortable. When you are done, come on down and find me, and we'll go from there." I said.

She grinned and did just that, leaving me to relax and enjoy the coffee. I did have a bit of an ulterior motive. My apartment lease was due to end, and I felt it was time to move on up in the accommodation world into something more than cramped student style digs. After checking the ads in the local paper, I found a couple of possibilities and circled them. A lot more than what I was paying now, but an upgrade.

I settled in to read an e-book. It took a while, but suddenly she appeared with a big smile on her face as she sat down opposite me startling me a bit. and set the shopping bags down beside her.

"Miss me?" she grinned, "or just surprised to see me?" she quipped

I laughed "No, just wrapped up in this book."