The Stowaway's Keeper - Cover

The Stowaway's Keeper

Copyright© 2024 by HppyHrryHrdn

Chapter 14: Calgary

Erotica Sex Story: Chapter 14: Calgary - In the 80's, John was looking to go some place no one would know him. He was not planning on starting his new life with a 14 year old girl. She and her friends keep his life anything but mundane, despite his best intentions to keep it that way at his new home. Codes will change as story progresses.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   ft/ft   Fa/ft   Teenagers   Coercion   Consensual   Drunk/Drugged   Reluctant   Fiction   Humiliation   Anal Sex   Analingus   Slow  

Pretty much on queue; two days later there was a call. I picked up before Cheryl could get on the line. On the other end was Dorothy. She got straight to the point of the call with no preamble. “Hi John. I thought about it. Will you please show me all sex can be?”

I figured she wanted the call quick and said, “Hi, Dorothy. It’d be my pleasure and hopefully yours. But you have to be sure and mentally prepared for all kinds of sex. Because to know what all it can be, you have to experience some of all of it.”

“I can do that,” Dorothy stated with a bit of trepidation.

“OK, but you have to be wholeheartedly committed. Nothing is off-limits until we leave, so you have to be completely sure. I will not hold it against you if you change your mind and don’t show. It will be like we never planned it.” I informed her, having already thought of several activities, some pushing the limits, others over them.

The trepidation only got thicker. “I’m completely sure, I’ll love all of it,” she was clearly trying to convince herself.

“OK, I’ll meet you this Saturday around lunch, and we can spend the rest of the weekend at the Palliser Hotel in Calgary, leaving on Monday. When you get there, ask for Mr. Polo’s room.”

Dorothy didn’t ask about the name and just said, “OK, the Palliser in Calgary, Saturday. I’ll be ready.”

Later that day, I told Cheryl, “I have some business this weekend that needs to be taken care of. I’ll be leaving on Friday morning, before your lazy butt gets out of bed, and should be home by Tuesday at lunch at the latest. You can have Helen come over for the weekend again. Maybe you two can commiserate together. The poison ivy might be more bearable by the time I get back.”

“OK, sounds like a fun girls’ weekend. It’s going to be a three-B weekend. Boys, booze, and boning.” She laughed.

Sure, she was joking about the two of the three ‘B’s. I said, “Very funny.”

“I thought so,” came back. Cheryl sounded proud of her cleverness.

“Good,” I said. Then continued with one of my, I am serious as a heart attack looks. “I am going to be serious for a minute. And you need to listen closely ... This weekend, while Helen is here, Helen’s uncle Paul may come looking for her. You two are not to talk to him or let him come over. No matter what he says, under no circumstances should he be allowed to step on this property. If he does, you should do what I’d do if a person came to hurt you. Don’t think, just shoot and continue until the clip is empty.”

Cheryl looked at me like I’d grown a third head, suggesting she shoot one of Helen’s relatives. I stared at her intently, “You know not everybody’s relatives are good people.”

She nodded her head like she understood what I meant, “OK, John.”

Even later that night, I called Marco, “Hey man, I need to borrow your pedigree for the weekend. I have some business in Calgary.”

“Sure, man, no problem. I am glad to hear your international business is going well. You going to be bringing me back some Cuban’s?” He asked, knowing the correct way to phrase our conversation in case we were being listened to.

“No, man, you know bringing that back isn’t legal. Is your standing still good at the Palliser?” I said, letting him know I wouldn’t be bringing him any new people and I would be staying in the penthouse. In his line of work, it was good to obfuscate where you were. My telling him where I would be staying in the hotel provided him with a secondary location if anybody ever had questions about where he was. Or tried to verify an alibi. Being in multiple places at once was a great defense.

I arrived at the hotel about twenty-four hours before I expected Dorothy. I checked into the penthouse under Marco’s name and carried my small suitcase up with me. The suitcase had all the items that would be needed for the weekend. Plus my usual personal protection. I finished setting up the room the way I figured would be conducive for teaching Dorothy. I talked to the staff, letting them know a brunette would be in the next day asking for me. They should give her the room number and let her come up. That would be all we needed for the rest of the weekend unless told otherwise.

Like an excited child on Christmas morning, I got up early. I was anxious about me and Dorothy exploring her body and letting her discover new pleasure zones. She showed up earlier that day than we had planned, at eleven in the morning. She knocked on the door, and I opened it to find her dressed in a tight black skirt. It hugged her hips and cradled her round ass before going down and clinging to her firm upper thighs. Thighs, that despite being close to ten years my senior, were still ones someone ten years my junior would be proud to have. Her pink blouse was loose and beneath it. I could make out just a little of the lace of her bra. Its black edge peeked through where she had left the buttons open down her cleavage. Two buttons further than what she would have had she been going to church. Not that the whole ensemble wouldn’t have grabbed everyone’s attention away from the service. Coming out from her skirt were sheer black stockings glued to her legs, making every curve and muscle look more refined. She was a little unsteady on the high heel she was wearing below her honed calves, which curved beautifully.

I held out my hand and said, “Welcome. You look utterly amazing.”

She blushed and, looking down, said quietly, “Thank you, but I’m not that pretty.” She put her small suitcase inside the door and let it close.

I backed away from her, but just a second. I took her dainty, strong hands in mine, holding her arms up, causing her head to rise. I held them there until she looked me in the eye. Still holding her arms out in front of her, I began looking at her from head to toe. I was letting her know; I was evaluating every part of her by turning her around as she wobbled on the heels. When she was back facing me, I said, “Remember, wholeheartedly was our agreement. And compliments on your appearance are part of that. But even so, I stand by my original statement. You look utterly amazing. There can’t be a prettier woman in the whole country.”

Her blush became deeper red and extended down into the cleavage, making the pink look that much brighter. I kept a hold of her hand, guiding her further into the room. Ahold of her hand and guiding her in, I noticed the care she had taken to paint her fingernails. The short fingernails were a shade of pink that matched her blouse. Holding her hand, I could feel it trembling. And it wasn’t just her hand. Her whole body was quaking as she took more steps into the room.

I walked her over to the small table in the suite and cheerfully asked, “How was your trip up?” I hoped the cheer hiding my apprehension didn’t sound as fake to Dorothy as it did to me.

She was completely honest as her voice cracked, “On two occasions, I almost turned the car around. But seeing this beautiful view and luxurious suite and knowing you’ve planned the weekend for us. I’m glad I didn’t.”

I too was glad she hadn’t and said, “I’m glad you didn’t also. And so you know, no matter what occurs over the weekend, it’s nice you’ve agreed to join me in considering and trying all I’ve planned.”

Dorothy went and stood in the window. Her eyes were gazing out over the skyline, and she said, “I’m glad, too.” The sun shone through her hair that hung down leisurely on her shoulders. The chestnut brown contrasted nicely with the satin pink blouse, and the light danced through the curl at the end of her hair. I wondered, looking at her, how she had escaped her house looking the way she did without raising any questions from its occupants. When she turned back around, I noticed that she was still extremely tense, and her chest rose and fell unnaturally.

Continuing to admire the form in the window, I said, “It’s okay to be a bit apprehensive. I’m nervous, too. I’ve never done this kind of thing, whatever it is, before.”

Dorothy turned and studied me with a bit of disbelief. “You haven’t met up with a woman before for sex?”

I almost laughed at her comment but only grinned, “No. A planned getaway with a woman for a weekend is usually not just for sex or teaching all kinds of different sex. We’d have conversations and would have a plan of places where we were going to go. Plus, other things we’d be doing besides having sex. Most of those women were in one of two categories. Strangers, who the plan was to have a weekend away for fun that would likely result in us never seeing each other again after the weekend was over. Those women were very experienced and knew exactly what they wanted when we finally got in bed. The other category is long-term girlfriends. We’d be just on a quick junket and it wouldn’t be our first time in bed together. Those weekends were usually not just for sex either, but a weekend of making love between the trips out sight-seeing. I can say honestly, there have only been two of those. So no, I don’t do this, often or ever really. You are truly one of a kind in this regard. I fully expect to see you again. Not necessarily in this setting, but possibly. And definitely in church, or around town, and when Cheryl and Helen are done playing together.” The double meaning of that was lost on Helen’s mom. “Plus, this shall be the first time I don’t know what to fully expect at the end of the weekend.”

Dorothy laughed and giggled nervously, “Yeah, I don’t know what to expect at all. Up until you said it the other day, I didn’t even consider something like this would ever be possible. I’ve never imagined in my whole life, I would go somewhere to have sex. And sex that even resembles fun is a foreign concept. I’ve not even had sex for making babies for the past fifteen years.”

The fifteen-year thing threw me for a loop. I couldn’t comprehend how she had been living with her husband for so long and evidently only having anal sex. Even then, it was only when he was in the mood. I said, “Maybe all this talk of sex is making it a little weird. How about we maybe not make it so weird? We can just sit here for a while and have a cup of coffee and talk about anything other than sex or why we’re here.”

My ability to put my foot in my mouth was far exceeded this time, as Dorothy said, “Sure, that makes sense; we should get to know each other better.” She then joked, “And not biblically, right now. Plus, I know so little about you. You know a lot about me. So is there anything I need to know about you? I guess you could tell me your story of how you got to our little town and how you ended up there with Cheryl as your ward.”

It was my turn to hem and haw, “My story is really long and boring. Sufficed to say I come from down south. I joined the military at a young age when it wasn’t popular to do so. Due to much of my military service, I still can’t talk about it. And I landed in Montana.

Despite not really saying anything, she appeared interested in hearing more. “Well, at least how did you ... or why did you end up with Cheryl? You seem to love her a lot. But you’re so young to be responsible for a girl her age.”

“Yeah, I do love that crazy street urchin stowaway,” I stated. “I was the person she picked when all the other people in her life weren’t good for her.”

“God, I wish I’d known you when I was her age,” Dorothy stated, turning up her coffee cup.

For a little levity, I said, “Well ... I’d have been like five. I don’t think I would’ve been much help. I guess you could’ve babysat me.” I got up and took her cup, refilling it with coffee.

Dorothy sat there staring out the window for a minute before saying, “Great, and now I know I’m old.”

Reaching around her, I put the full coffee cup on the table. Brushing her long, soft hair from her smooth neck, I felt her jitter as my breath bounced back to my nostrils, picking up a hint of perfume. I said quietly to the back of her ear, “You’re not old. You’re like a fine wine that’s aged beautifully so I can savor your every flavor, aroma, and texture ... God, you are gorgeous.” With that, I softly put my lip on the heated, blushed skin of her neck. The feel of her skin between my lips as I captured a bit of it. It was silky smooth. As my lips caressed her skin, the pounding of her heart was imparted to them.

She tilted her head as my lips remained on her moving, ever so slightly gathering in a new morsel of her sensual skin. From her almost immediately was an airy, “Mmm ... Oh God, I’m doing this ... I’m really doing this.”

Letting go of the cup and taking my hand from her arm, I had both of them cup the undersides of her covered and shivering breasts. I let my lips leave Dorothy’s neck for a moment to tell her, “Yes, we are ... and if it’s all like this, it’s going to be truly heavenly.”

I re-attached my lips to Dorothy’s neck, which she had graciously exposed for me. The sensations on my lips were the combination of her trembling, her heart pounding as it raced, and the vibration of her light moans. They started as I closed down gently on the breast in my hands. I carefully eased her out of the chair she was sitting in, not letting my lips leave her delicate skin.

I stood the five-foot-six woman in front of the window panes that extend down to her knees. She seemed so alive with the sun shining on her face as my kisses worked up to the back of her ear. I let one of her breasts pass from my hand so it could find the first of four buttons. Dorothy’s blouse hung open with an inch divide after each of the buttons slid through their hole with ease.

Freed from the duties of unbuttoning the garment, my hand slid inside the pink satin. Dorothy again jumped with the first touch of my fingers to the smooth skin below her bra. I had captured her dainty hanging earlobe between my lips while I brushed over her lower ribs, counting them. The indention between each one was caressed before going on to the next one further down. When I ran out of ribs her quaking stomach was stroked. Soon both hands had opened the blouse up completely. It permitted them free access to all of her stomach and up over her bra. My fingers found the small indention in the center of the luxurious expanse they traveled over. Dorothy’s stomach muscles quivered when the edges of her belly button were investigated.

While my hands were slowly learning the texture of Dorothy’s taut satin skin, my lips returned to her neck via the back of her ear, which tasted exquisite. Still familiarizing myself with her stomach, I pressed her back tight to my chest. I felt the purrs and moans that came after she caught her breath following her lace-covered breast being stroked over.

The lace felt hot in my palms as they froze in place for an instant. The bump beneath the covering being gently pressed down instigated the temporary cessation of Dorothy’s breathing. Only to have it start back much faster as her bra continued being skimmed over. The mostly see-through garment held her perfectly sized tear-dropped breast, which rose and fell rapidly.

For just a few seconds, I parted my lips from Dorothy’s neck, looking at our reflection in the window. The reflection in the glass revealed her blush extended under the lace. Plus, her face showed both desire and trepidation at my kisses, and my hands were still being filled with her breasts. Trepidation turned to fright as her own shaking hands slowly brushed the garment off her shoulders. The garment stayed trapped between our bodies as restarted kisses went down her neck to her newly exposed shoulder.

An unsteady hand had its pink-painted fingernails running through my short hair. When my lips opened wider and I nibbled on her shoulder’s gentle slope. Sliding a hand up the other side of her neck, I lifted her hair up out of the path of my lips. The pleasure she experienced from the light tongue-tip touches at the nape of her neck was felt in my other hand on her chest as her purrs and moans grew in intensity.

I passed my lips over to the other side. For a second time, I got a quick glance at our reflections in the window glass. Her fears seemed to have lessened, but the tension in her body’s reflection remained. I moved back a half step, continuing to ply kisses and light nibbles along her shoulder. All the while skimming against her arms, straightening them. Once straight, gravity finished the removal of the pink garment. It fell across my shoestrings.

In the warm light, the black lace against the backdrop of her fair-skinned chest and flat stomach with its cute oval indention was a painter’s dream. Seeing just that much of her exquisite body made me sure her husband was truly gay or a damned fool. No straight man would’ve gone years sleeping next to such a sight and not put his lips to her. And I wasn’t going to be such a fool.

Letting her hair fall back over her shoulders naturally, I began kissing her neck and fondling her ear with my tongue. My hands again caressed her breast through the lace, over her stomach, and along the tapper of her sides. Slowly going down and up her back, my lips covered all of her neck and shoulders, while my hands did the same to the front of her. As I did so, her smooth skin became covered in goosebumps.

Dorothy stood almost mannequin still except for her continued quaking when my attention turned to her skirt. My hands left her flat tummy and dispensed with the button at her waist as fast as her blouse buttons were undone. The zipper was next to go as my fingers followed its path around her hip. The tight skirt didn’t fall from her as the blouse had done. But the view once I had pulled it from her hips was spectacular. I hadn’t been prepared for how delicious her round ass or vulva would look. Most of her ass was bared, but over the outer curve of each ass cheek’s pale skin was a thin black strap attached to her black nylons. Seeing the price tags still attached to both the lace bra and the garter belt, she said she wasn’t in her usual undergarments. Yet again, she hadn’t any cover for her pussy.

And the image I saw in the window was getting more incredible as each clothing article was removed. Dorothy evidently had become immobilized by my slowly stripping her while my lips caressed the edge of her ear. She didn’t move a muscle except to tremble. I quickly unsnapped the clasp of her bra. Like her blouse, it was brushed away by my hands. Released from their pretty captive garment, her breast hadn’t sagged when released and had only jiggled. The teardrops were full, but unlike so many women, her tits were just like I like them. They didn’t lap over like a fat man’s belly does but held their shape so all of her under-tit’s curvature was visible.

It was then that I got the first unadulterated feel of her breast’s flesh, while the undergarment quickly fell from the petrified woman. She reflexively jumped at the first touch of my hands being filled with her naked flesh. The touch on her bare breast had her frightened ask, “Oh God, what are you going to do?”

The full sight in the window’s reflection was spellbinding. I wasn’t prepared to let her chicken out before she had given it a full-hearted try, as she had promised. She had been amazing standing in the doorway dressed. Yet, now with the sun coming through the window, it kissed her mostly naked body. She was so far beyond ravishing. Into the ear, I had been tracing with the tip of my tongue. I didn’t answer but whispered, “You look absolutely exquisite. Your body is to die for.”

My voice had broken her trance. Her hand shot to cover her pussy, and her other arm went across her breast. “God, no, I’m ugly or plain on my best days.” Bashfully, she added, “No one wants to see me naked in the light. Paul and Frank only wanted me when it was dark.” A second later, she realized where she was standing. “Oh my God, I’m naked and people can see me.”

I didn’t let her go when she tried leaving the window. Instead of letting her back out of the window, I had her take another two steps towards it until her knees hit the window sill. “Yes, they can. And they can see you’re beautiful. You have magnificent breasts and a pussy that could be on a teenager less than half your age. It is part of your learning to be and experience sex. That you are a ravishing sexual woman. You need to stand here in the window, and like a goddess on high, let the mortals look up and worship your perfection.”

I gently guided her hands away from her pussy and breasts. Her trembling and horror at the idea made her knees weak to where I had to grab her hips and steady her. With my hands filled with her hip bones, I kissed her just as before. She again tried leaving the window. “I can’t stay here. I’m so embarrassed.”

I needed to break her of her self-doubt and her low opinion of herself. Unlike Ryan’s and Sheila’s breaking, this wasn’t for punishing her. So only a carrot would be used to get her to step out of her comfort zone. I turned her around so she was mooning the city below with her well-used ass. Before locking her in an embrace, I said, “Please stay here and let this mere mortal worship you and your goddess-like beauty. But let me do it while you’re on display on high.” I wrapped my arms around her naked body, pulling her tight to me. The heat of the body permeated my clothes where her skin touched them.

She leaned in and pressed her lips to mine. She mashed her lips on mine with her horrid technique. I would have told her to stop if it had helped further my goal of having her enjoy sex. Which in turn might make Helen’s life better. Instead, I tried to teach her without her knowing what I was doing. I didn’t mash my lips back, making the kiss very one-sided. After a while, Dorothy stopped attacking my lips with hers and gently mated them up with mine. The new kiss, while not horrid, wasn’t yet sensual or hot. I let my hands, which had held her shoulder blades tightly, slide down over her firm ass to the curved crease at the joining of ass and thighs. I cupped the solid orbs, squeezing them, lifting her to her toes.

Dorothy squeaked as my hand lifted her. Leaving her lips, I asked, “Are you ready?”

“Ready for what?” She answered.

“To stand on high and have your body worshiped,” I replied, putting a kiss under her jaw and holding it for a couple of seconds.

“You mean you want me to stand here in the window?” she shuddered at the idea. The blush that had almost finished fading came back across her chest.

“Yes, and let your body be worshiped, like it and you should be,” I said.

“What does worship entail?” She sounded less scared but still resistant to what I had suggested. I had expected as much. While she had come to the hotel. It was going to take a lot to break old habits, even if she thought she would be open to trying new things.

“Being given pleasure. Pleasure for pleasure’s sake. Pleasure because you are worth all the pleasure and more a mere mortal can give you. You know the cunnilingus Paul always started?” I asked

Some excitement crept in with the earlier fear, “You’re going to lick me?”

“First, I am not a dog, and you’re not a bowl of water. It’s called cunnilingus or being eaten,” I said. “Second yes, but I won’t be stopping when it just starts feeling good.”

“You mean it will feel better? How much better does it get?” she asked.

This time it was me putting my lips to hers. She again attacked my lips with hers. For a second time, I moved my head so her attacking lips lessened their pressure on mine. With the pressure lessened, I gently captured her lower lip between mine. She seemed to understand and followed my lead. She lightly sucked my upper lip in between her supple lips. Having furthered her kissing abilities, I got back to her question.

My answer would require some show and tell to put a trap in place. I slid my hand between her legs, going up around her. My middle finger separated her hair-covered fat lips and the thin pink ones going up the front of her. Dorothy gasped and jumped at the touch of her sex. She exhaled heavily when the finger hit her clit. I wiggled her clit under my finger before sliding its tip to the base of the folds split. Dorothy’s voice was throaty, saying, “Oh God, so good.”

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