The Love of My Life Pt. 07


The Love of My Life — Part 7

This is the continuing anthology of my sexual awakening by the man whom I married and love to this day.

It is a warm summer’s evening. The sky is clear, not a breath of wind. I have taken Rob to my favourite spot on the northern prairie, on a gravel road atop a small hill. Farmhouses are in the distance, the golden wheat in the fields spread out below and around us. To the west, the sun is above the Rockies many kilometres in the distance. I lean back into the warm embrace of my “Cowboy”, the nick name I have given my city slicker boyfriend.

As I bask in the surprising warmth still radiating from the sun, I feel Rob move his hands from around my waste and undo the clasp at the top of my summer dress. He slowly moves the zipper down, gently pulling the dress off my shoulders and letting it fall to the gravel below. I make no sound in protest, holding my breath, surprisingly aroused and undisturbed by this exhibitionism.

I close my eyes as next I feel him unclasp my bra. I raise my arms and bend forward a little as Rob slowly lifts my bra straps over my shoulders to let it drop to the ground as well. He does not reach for my breasts, which ache for his touch. Softly his touch lingers upon my back, caressing my shoulders, my ribs and tummy, until I feel him hook his fingers into either side of my panties. He bends slowly to one knee, pulling my panties down to my ankles. At his touch, I lift one leg, then the other while he pulls my clothes away from me. I stand with my feet, shoulder length apart, naked to the world save for my running shoes still on my feet. Slowly Rob raises his hands following my legs to my ass. His left hand continues up my spine then around to my tummy. His right snakes between my legs, his thumb pressing upon my anus, his fingers spreading the lips of my labia. I am wet, aroused and my breathing has become more shallow. He nips at the left cheek of my ass as he pushes his fingers featherlike over my clitoris. I thrust into his hand, want more pressure on my clit.

“Let me in,” he breathes into the small of my back. I know what he wants.

“No,” I moan in response. Roughly he plunges two fingers into my cunt, and once more demands that I let him “in”. I relax, push back my ass and try to relax as I feel his thumb popping through into my rectum.

“What do you want?”

“I want you to fuck me,” I respond. I pull away from him, and turn towards the front fender of his Audi. Spreading my legs, I bend over, supporting my upper body on my forearms upon the engine hood. With my most sultry look and voice, I look back over my shoulder at Rob.

“C’mon Cowboy. Fuck me!”

I turn to face the vista below, and wait for the feel of his hips against my ass, the thrust of his cock into my cunt. But Rob insists on teasing me. He pushes me further onto the hood of his car and grasping my outer thighs, lifts my feet off of the ground. Instead of entering me, he slides his cock first back and forth between the cheeks of my ass.

“Are you ready to give me your ass,” he growls.

“No, please, you are too big,” I moan.

“Maybe you need to come first, and then I can fill your ass?”

“Yes,” I respond. “Please stop teasing me and fuck me now!”

But again Rob defies me. He pulls back, lifts me higher and pushes his cock past and through the lips of my pussy, slowly sawing his cock back and forth along my clit. I moan in frustration and lust when ….

My alarm goes off. A huge sense of disappointment comes with my waking. I want to resist my growing consciousness, desperately hoping to get back to that hill on the prairie and feel him entering me. Instead, I am now awake, alone in my bed with fingers moist from my pussy. I give voice to my frustration — Rob is back in Toronto for the summer, and I am lying in his bed, masturbating in my sleep.


The spring of 2007 had brought about a great many changes to my life. Laura, my room mate and best friend from childhood, had completed her B.Sc. in computer engineering near the top of her class. Most of her classmates had flocked to Silicon Valley to earn the big dollars, but Laura had been awarded a huge grant to enter the Ph.D. program at Caltech on the promise she would return to teach in Canada. As Laura put it, three or four years in Pasadena had to be better than wintering in Edmonton, Alberta. Which meant I had to find a room mate.

Of course my boyfriend Rob had offered the immediate solution — give up my apartment rental and share with him the two bedroom luxury condo owned by his grandfather, with the second bedroom being our combined offices for school work. The idea of waking up to this man every morning was incredibly appealing, and to my surprise, my strict Catholic parents didn’t appear to be fussed about their daughter shacking up with her boyfriend. Rob was now 22, going into second year law next year, and I was about to turn 25 entering third year medicine. As mom said, “You’re both mature adults. Do what you feel is right.”

The summer had however porno been lonely. Laura and I gave up our apartment at the end of April, she moving home for the summer. Med school classes went for a month longer into May, and Rob had helped me to move into his place before returning to Toronto at the end of April to spend the summer working with his grandfather’s business group. Since his teenage years, Rob had been learning his grandfather’s business as the still unknown heir apparent to this large manufacturing and retail conglomerate — unknown because Rob didn’t share his maternal grandfather’s surname. He had risen from being a single outlet employee in high school to a well paid summer intern with various divisions as part of a corporate grooming of bright upcoming student talent, all he believed without the interference of his grandfather. His real schooling about how to run the companies came every summer night over dinner with his grandfather.

I on the other hand had spent a few weeks at home in June, and then begun “clerking” at the local university hospital system where U of A med students spent a year starting July 2. Our education for twelve solid months was working at the very bottom of the medical food chain with interns, residents and attendings and completing research and other papers designed to demonstrate that we were still learning something. In 2007, we were exempt from any employment standards — expected to put in twelve hour shifts, ten days on, then four days off to recover; nine days on, then five to recover. Thank God we didn’t have to work graveyard.

While Rob and I tried to talk nearly every night, occasional phone sex had been a very poor substitute over the summer and with the end of August in sight, I was beside myself with yearning for his return at month end.


It was after 8 o’clock in the evening in mid August when the condo’s land line phone rang. That was a rare happening, as both Rob and I relied almost exclusively on our cell phones, the land line coming free with the internet provider to the condo. I saw it was a (416) number, and curiosity caused me to pick it up on the fourth ring.


A deep male voice on the other end introduced himself as Rob’s grandfather, Lorne. I immediately became aware of the genetic source of Rob’s wry sense of humour. Lorne said that since he had heard that I loved his grandson, that seemed the common thread upon which to start to build a friendship between us. After establishing I was free to chat, I spent the next twenty minutes being charmed by this gentlemen as he coaxed me to do most of the talking about my family, studies and interests. Realizing that it was starting to near midnight his time in Toronto, I told him I didn’t want to keep him up. At that, Lorne got to the point. He understood from Rob that my birthday was next week. Would I have a break in my hospital clerking duties before Rob had to return to Edmonton? When I told him I would be having five clear days the following week, he said he wanted to give Rob and I a mini-vacation if I had a valid passport. When I replied in the affirmative, he promised his office would send the travel details to my email address before I was home from work the next day.

“Where did you have in mind,” I asked?

“Let me surprise you,” he said, and wishing me a good night, he hung up.


Flying executive class from Edmonton to Vancouver was a treat. Seeing my boyfriend for the first time in nearly four months in the Air Canada lounge at YVR was a longing fulfilled. Walking later that evening through the resort into a prime ocean view grand suite at the Four Seasons on the Big Island of Hawaii was a complete mind blower.

I walked around open mouthed as our bell boy deposited our bags and gave us the tour of the suite before Rob sent him on his way with a generous tip. The suite was bigger than Rob’s condo. Although past midnight for both our time zone internal clocks, Rob opened the fridge to find it stocked with California wines. Quickly opening and pouring each of us a healthy amount of chardonnay into acrylic wine glasses, Rob toasted our “First Honeymoon” and after a couple of sips each, put down our glasses and took me into his arms.

“Grab your glass and let’s find the shower,” Rob said. Reaching for my hand, we proceeded to the back of the suite where a glass door led to a fully enclosed room lined with lava rock and stone walls, open to the sky, and one very large rain shower head the size of a pie plate.

The air was warm. A light gentle breeze from the ocean gently fell upon my face. The lighting was subdued and appropriately romantic as Rob turned on the shower. Slowly, we took turns removing each other’s clothing between kisses until finally, we were naked and in each other’s arms. Our tongues began this gentle dance as I pressed my breasts into Rob’s bare chest. Separating his legs, I forced myself upon his right leg as I relished this welcomed make-out session with my man, grinding my clit upon his hip. Pulling back my head, I gently pushed my tongue into his ear, holding his head with my left hand, and stroking his hard cock with my right.

“Fuck me now,” I breathed into his ear. “I need you to fuck me now and really hard!”

When I tried to pull him back into the bedroom, Rob responded with “First we get clean before we get really dirty,” and with that, pulled us both under the warm shower. Pumping shower gel into both hands, he began to soap down my shoulders and breasts. Then with the water spraying my back and below, his soap lubricated hands pushed me with my back to the stone wall out of the shower spray. Aggressively kneading my breasts, his thumbs and forefingers pinched my nipples and caused me to moan in a mixture of pain and pleasure.

Next Rob pumped more gel into his hands, and turning me around so that my hands were pressed to the wall, Rob soaped down my back, my ass and moving to his one knee, both of my legs. Rising to take me in his arms and rub my soapy naked front against him, I moved continuously, thrusting my breasts across his pectorals and his cock against my tummy before he pulled me back under the showerhead to rinse me.

I had discovered Rob had two fetishes: my ass and legs in expensive silky pantyhose alone; and my ass. He was determined I felt to fuck me in my ass, but had over the school year only teased my anus with the insertion of a finger or two, or the threat that someday my ass would be his completely. Thus I was not surprised with his putting a soapy finger past my anus and into my rectum, which he began to push against my female parts from the inside of my ass. This I allowed for a minute or two, before pulling back and telling him it was my turn.

“Turn around and lean your hands against the back wall,” I told him as I reached for the pump bottle of shower gel. Applying the soap first to his back and shoulders, I reached around him and soaped his chest, cock and balls as the water showered down upon me. Grabbing more soap, I then dropped to one knee to soap his ass and legs, then spun him around to rinse us both off again.

“I’m not finished with you yet, Cowboy,” I told him as I rose to my feet. “Hands against the wall again, and spread your legs”.

“Such a bossy kid,” were his words as he complied.

Grabbing a handful of gel, while rubbing my pussy against his hip, I placed the soap at the entrance to his anus. When Rob gasped in surprise, I gently admonished his reaction. “Now baby. How often have you told me to trust you, relax and to let your finger into my ass?”

Frankly I was shocked at my level of arousal at the threat of turning the tables and finger fucking his ass. I had come a long way from the vanilla good Catholic girl Rob had first met last October in Edmonton. As he relaxed, I pushed one, two then three of my longer fingers into and out of his rectum with my right hand, squeezing his cock with my left. Grinding my pussy hard against his hip, I gently bit his shoulder as this 6’3″ mass of masculinity surrendered to this perverted game of me masturbating him while I finger fucked his ass.

“It’s not “gay” for me to want to do to you what you do to me, you know,” I told him. “How does it feel?”

“Different, I don’t know.”

Pushing my fingers to rub against his prostate, I whispered into his ear, “Different bad, or different good?” Sensing his hesitation, I pushed harder against Rob’s prostate and concentrated my other hand on the crown of his cock.

“It feels good, doesn’t it Cowboy. Kinky, perverse, but you love your girlfriend finger fucking your ass, don’t you?”

“Yes,” he whispered in reply, perhaps too afraid to really admit it.

Sensing he was close, I pulled out of his ass and swung him around to face me as I dropped to my knees. As the shower poured water onto my head, I took his cock as deep as I could into my mouth, and plunged my fingers back into his ass. Sucking his cock with all the vacuum I could create while continuing to massage his prostate with my long fingers, Rob grabbed my head with both hands and began to fuck my face. Then hearing him groan in release, I felt the jets of his cum in the back of my throat. As he writhed, I continued to suck all of the cum he had yet to give into my mouth until Rob, unable to take any more, pulled himself out of my grasp and sat down in front of me under the shower. I grabbed more shower gel to wash my hand, and crawled into his lap, where we continued to make out.

Looking into Rob’s eyes, I grasped either side of his head. “I am still waiting to get fucked, Cowboy! What’s it going to take to get that cock of yours hard and ready for action?” Still enjoying the dominant, a role I too rarely got to play, I stood up to put one leg over his shoulder and force my pussy into his face, leaning my hands against the back stone wall for support.

It might have been the pent up desire. It could have been the taboo kink of so dominating Rob as I had done for the last ten minutes. Perhaps it was the open sky, stars above with the warm shower water cascading over my back and shoulders as I felt him grip my ass with both hands and plunge his tongue between my labia and against my clit. No doubt it was all three, but as my orgasm began to build, I kept waiting for it to come. Instead, it just kept building to a level I rarely experience. Finally, I began to shake and nearly collapsed as my orgasm erupted. For the second time in our lovemaking, I felt myself squirt into Rob’s mouth. Sealing his mouth to my cunt, Rob drank my juices, then helped me collapse back into his lap until I was recovered.

Drying ourselves with the huge Four Seasons towels, we returned to the single bedroom with its King size bed. Our bodies dry, our heads wet, we nevertheless fell into one side of the bed. We had been in the shower for nearly half an hour, and it was now past midnight at the resort, nearly 6 a.m. Rob’s time, 4 a.m. mine.

“You need to sleep more than I need to be fucked Cowboy,” I whispered as I gently kissed his chest. Hearing his deep breathing, I cuddled into his body until sleep took me as well.


Rob and I are still together after fifteen years because our euphemism for sex — “play” — was and remains only a small part of the deeper relationship between us. We still enjoy just being together, and that was how we spent most of our time at the Four Seasons.

At least twice a day we would make love — often slow and sensuously. However most of our time was spent enjoying the sun, pools, ocean beach and fabulous food the Four Seasons had to offer. Rob was equally needy with touches and hugs, to remind us both that we were back together.

My 25th birthday arrived midway through our mini — vacation. Rob of course insisted that we have a very romantic private dinner brought to our suite. I had decided it was time that I gave in to his second fetish.

After dinner when room service had taken away our dishes, the two of us sat on the lanai facing the ocean. It was dark, about 8:30 in the evening, the beach was virtually deserted. Our suite had two large sliding glass doors that when open, gave us a floor to ceiling opening at least 8 feet wide with a view directly onto the beach and ocean. We sat there on the couch, sipping wine, my calves in Rob’s lap as he lazily stroked my legs. I excused myself, and headed towards the ensuite bathroom. Enroute, I opened the night table on my side of the bed and grabbed the small bottle of KY Jelly that I had brought with me to Hawaii.

I had been practising over the summer, occasionally inserting fingers, later hair brush handles into my well soaped rectum while masturbating in the shower. Although I was hesitant to try taking Rob’s much longer and thicker cock into my ass, the very taboo nature of such an act combined with my wanting to give my love what he wanted had motivated me. Now seemed the perfect opportunity given how relaxed and happy we were back together after the summer separation. I pulled off my clothes and spreading my legs while bending over the counter, I pushed large dabs of the KY into and around my anus and rectum. Washing my hands well, I returned to Rob wearing only a soft T-shirt.

Walking into the “living” area of the suite, I was keenly aware that with the sliders wide open to the ocean view, anyone could see, or more likely hear any “playtime” I might encourage with Rob. Perhaps that’s why I kept on my T-shirt. My nipples pebbled as Rob’s eyes and face lit up as I slowly returned to where he was sitting on the couch. Dropping to my knees, I placed the bottle of KY on a side table, and reaching for Rob’s shorts and underwear, pulled both off of his legs. I had thought to take his cock in my mouth to get him really hard, but the sight of the KY bottle already done the job.

I straddled Rob, and began kissing him, taking his cock in my hand and rubbing it alon my pussy and clit.

“I have to be in control,” I said. “Nice and slow, and I will try to give my ass to you.”

Rob cupped my breasts in my hand through the soft cotton of my T-shirt as we French kissed and I continued to slide the pussy lips up and down upon the back of his cock. Rising up, I placed his cock to the entrance of my pussy, and slowly lowered myself.

“Oh, so good, so full,” I moaned into his ear. “Do you want to fuck my ass?”

“Oh God, yes,” Rob whispered in reply.

“Then don’t move Cowboy.” With that I reached for the KY and rising up on my knees, pulled Rob’s cock from my pussy. Squeezing a large dollop of KY onto the crown of his cock, I coated it liberally with my before grasping Rob’s cock and presenting its crown to my anus.

“Don’t move until I tell you,” I said looking into his eyes. Closing mine and willing my ass to relax, I lowered by ass a little, letting the full crown breach my anus and the entrance to my rectum. I remained absolutely still, eyes closed, silently chanting to my self to, “relax, relax, relax ….”. When I felt ready, I continued to slowly lower myself down, taking more and more of Rob’s cock into my ass. In what seemed much longer than a minute or two, the cheeks of my ass were flush to Rob’s thighs and I felt this incredible, perverse fullness.

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