One Journey at a Time Book I: Homeless Luck, Vagrant Jackpot Act I

"There comes a time in a man's life that quick action is a result of guts, willpower and lust reaching the boiling point."

At one point in my life, I experienced running away from home. To be precise, this particular incident already counted as my 4th. I and my mother, the "Empress Dowager" of my house (or so I see her as such) had rows too many and I decided, enough is enough. Confident of myself, my particular set of skills, my good looks and extremely blessed by Lady Luck, I set out; vowing never to return.

Having employed with an excellent managerial post also added to my well-bloated ego.

With no specific plans to pay my own rent and such, I wriggled out of my dilemma by asking the generosity of one of my office mates. She was actually my mentor when I first started with the company we both worked for. Right off the bat, I knew then and there that she was something. She's actually married with three kids, her youngest: a son who was then 9 months old. Despite that, she's still on her prime. At 5'2", her height is well complemented by her well-proportioned body. Her bust was what that first caught my attention. During that time we're not required to wear any kind of office uniform so she's always on light blue jeans, button-on short-sleeved blouse (which failed to hide her bust through her noticeable cleavage), minimal make-up and just a touch of rose red lipstick. Her hair's black and shoulder-length that's always free-flowing, no headband or clips or whatsoever. Fair-skinned with a light tan hue, typical of the female race of our nationality. To complete the picture of her, I'd say she's one of the prettiest ladies I ever have.

With some life experiences sharing, a little storytelling, a hint of persuasion and the right mix of facial expressions and shoulder shrugs I got her to say yes. She allowed me to stay in her place. Provided, I can sleep in what she calls " their tiny mezzanine" and pay for my own expenses; meaning, my daily food and hygiene needs. Of course, I told her I expect as much and even presented I give share to the house rent and utility bills (though, in the back of my mind, I strongly hoped she declines) but she (much to my relief) said no. All she wants, she said that time, was I abide her house rules during my stay there.

When I moved in, I was introduced to the rest of her family. To her kids, to her younger sister (who was also staying in her place as a housemate) and finally, to her husband. All of my expectations about him were a little off of the mark. He proved himself to be a good fellow with a sense of humor. He's not particularly good-looking but (kudos to him), he kept a body figure that is gym worthy. His work demanded much of his time, more by traveling to the various warehouses he's assigned to inspect. He would be in the house around six in the evening and be out as early as 3 AM.

By the way, my mentor's name is Cherry and she's the subject of this anecdote.

Her sister, Joan was mostly, out of the house and if she's sleeping there, would be up and out at 5 in the morning. Working student. Admirable, right? Anyway, Cherry's kids were actually with her mother who was 3 blocks away. The little ones would only be in the house in the weekends. It was, one of the reasons, why she allowed me to stay in her house as their additional housemate. Our work starts at 9 AM and it's an eight-hours shift. Her place is conveniently located near the national road and it's just a mile away from the office so we usually started the day at 6 sharp, be on the road and rode the jeep to the office by 8 AM. So, as you can see, from 5 AM onwards, we (Cherry and I) were the only souls left in the house.

She became comfortable (too comfortable, I should say) with me that it even came to the point that I could see her naked (only the bath towel covering her body) around the house. For the first two weeks I stayed there and particularly if someone else was in the house with us, she locked the door of her (hers and her husband's) room but gradually, she'd left it slightly ajar even if she's undressing or dressing and despite the fact that from where I slept in the house, I could have a view of the inside of their room.

You can say that the relationship we had that time is not that of a "mentor-protege" type but more of a "college buddies- tipping on the side of flirtatious passes type". In the office, we're strictly professionally civil but during breaks and lunch; we sat side-by-side, shared the same cup/glass and freely hugged each other. We also had a secret set of body language which would imply many different things that only the two of us knew of.

The most I can remember of her is the way she winked and pouted her lips at me whenever she had the chance. Then, on our way home, she'd teasingly nibbled at my ears while whispering sweet nothings or reminding me of her winks and pouts. We held hands fearlessly while riding public transport.

Then, the day came.

Our cat-and-mouse flirtatious chase ever since we met finally reached the climax.

One morning, (some days within the third month of my stay in her residence), I was going down the stairs to get hot choco when I bumped into her on the stair landing. She just came out of the bathroom, already bathed, her perfumed hair via shampoo fogging the room and invading my nostrils. Despite the clean fragrance of her hair, the moment her body collided with mine, I smelled her scent. Her own feminine scent, so captivating. To avoid her being sprawled on the floor due to our collision, I swiftly held her by her waist and gripped her left arm with my right hand. Due to the circumstances and the angle of our bodies, she was slightly arched towards me, her triangular mound almost connected to my crotch. I knew I was having a massive erection then and there and we both knew she felt it. Awkward due to our position for a few seconds, we both recovered by uttering at the same time, "Are you alright?"

Nobody tried to correct our position. Neither we did. We stared at each other for a few more seconds and with a rush of desire, I lowered my face to hers and initiated a kiss. A peck at first. Then, a few nanoseconds later, kissed her again. This time, longer but gently. Through that kiss, I passed the electrifying current of lust to her and both slowly adjusting our position, we managed to enter the bathroom together. I closed the door quick with a small kick and plastered her to the bathroom wall. This time, I held both of her arms by her wrist and pinned her to the wall. With smoldering eyes, she beckoned me to kiss her again. So I did, with increasing passion and intensity. Our tongues were twisting inside her mouth, most of the time jousting like two rapiers. Sweating and our saliva mixing with each kiss we shared intimately, we finally had to catch our breath and stopped. Both gasping as we savored the first surge of lust coursing through our system; I quickly gave her body a whole scan, admired again her curves and still considerably flat stomach despite giving birth thrice for the umpteenth time, I suddenly tore the bath towel away from her body. My sudden show of viciousness only heightened her sense of lust for I saw her bit her lower lip sensuously as her reaction. I started fondling her breasts all the while licking and kissing her. Her cheeks, her lips, her neck, her shoulder blades. Finally, I found her soft spot. Her cleavage. I sensuously let my tongue worked its way, gliding ever so slowly yet swiftly. As my kisses went lower so we're my hands. She moaned and groaned while her arms kept chained to the wall she's leaning to with invisible shackles, her body wriggled ever so gracefully whilst my mouth and hands kept working on her body.

"Ohh. . ." Cherry moaned.

Surprisingly, she still kept the volume of her moans to an admirable audible sound. Loud enough for me to enjoy caressing her with my lustful, sinful ministrations but soft enough to avoid being heard outside the three walls and a door of the bathroom we're into.

"Ohh . . ." She moaned still.

I kept her standing, looking like she's really shackled to the wall when I started licking her belly button downwards. Her small, barely audible, steady moans suddenly peaked to a gasp as she felt the first touch of my lips to her own pussy lips. I took my time, slowly inspecting the whole of her mound, started with the lips and gradually settled to her clits.

"Oh, ah, oh, ah. . . Ohh!" Cherry's moans were now having a note of exclamation.

Evidence that she more than liked what I was doing. In fact, she was more than accommodating. The pleasure that coursed through her body by my ministrations and merciless attacks on her clitoris was more than enough for her to take! Her previously motionless hands were now firmly nestled on my head, pushing so that I won't get away from eating her already flooding wet cunt. Even her hips were gyrating to the tempo of my tongue that flicked rapidly on her clit. With a downward, inward push with her hands to my head (with enough force to decapitate), she reached her first orgasm as I nibbled her clit and labia alternately in a furious rally.

"Ahhhh!" She gasped as her knees threatened to buckle under the combined pressure of standing for more than 15 minutes totally naked and from her enormous first orgasm brought on by my loving mouth.

I stood up, caressed her face with my left hand, tipped her chin upwards with my right hand and kissed her again longingly. I then held her again by the wrist with only my right hand and simultaneously let my left hand do the deed while kissing her nonstop. Cherry's moans came short as I continuously attacked her mouth with my eager tongue. She felt like burning with carnal desire as the fingers of my left hand prodded, fondled, groped and slid up & down and in & out of her wet pussy.

We both knew there is mutual consent and she freely gave herself to me by the time I locked the bathroom door and she didn't object. Yet, that time, we also both knew that the sexual act I was awarding her is almost the same as raping her. It's not only her body I was fucking. I'm also fucking her mind. For the second time, she came and her knees really caved-in through the sheer force of earthly pleasure. Still the gentleman, I didn't let her end sprawling on the bathroom floor. I lifted her up and bade her to sit on the toilet seat. She complied and by the time my cock got level with her rosy lips, I held her by the wrists again. She immediately understood what I wanted that time.

Still wearing my shorts (no brief though as that's how I am when I retire to bed for the night), she teasingly enveloped my very visible hard-on with her small mouth and sucked on it hard. Realizing it would only cause hindrance than added thrill, I worked on taking off my shorts while still holding her hands. I don't exactly know how but I did. Now, I stood completely nude and Cherry gasped involuntarily as she saw my cock. It's nothing enormous like what you'd seen on most porn videos but the wholeness of it on its full erected state is something. The way it's circumcised is also a little unique. It's one real hard cock.

Helpless with her hands held above her head, she started sucking my cock. At first she only sucked at the head, playfully ran her tongue along its circumference while its imprisoned on her warm mouth. Then, ever so slowly, she engulfed my cock on its wholeness down to the base of its shaft. She was following a rhythm only she was aware of but I have no complaints. In fact, I love each second as her mouth worked on my hardness. Within five minutes, my cock doubled its hardness and redness. The sensation in my groin is almost unbearable. Cherry knew how to excite me more.

I did all I could just to stop myself from ejaculating early. I remained motionless on my toes, avoided moving my hips to her rhythm. I let her do all the work-- with her mouth only.

Why? Because back then and there, I was fully determined to fill her cunt with my sperm.

When I felt that I was fast approaching the point of ejaculating, I let go of her hands and pulled her mouth away from my very excited cock. I motioned her to stand up and I replaced her on the toilet seat. Then I said, "Ride me".

Cherry obliged, slowly sat facing me. As my hard cock slid inside her, I felt her vaginal walls contracting on my shaft. It actually took less than a minute but for us two, drowning in the sea of lust, it felt like eternity. When she's finally settled, she gasped as she realized I was fully inside her now. We remained that way for two or three minutes, the both of us savored the sensation of finally becoming one in body. Then, as soon as she caught her breath, she fucked herself with my cock.

On and on she pumped, a beautiful sight to behold. I saw how her cunt swallowed my cock in & out its moist cavern. Her breasts swayed this way and that way to an almost hypnotic jiggle. Cherry's eyes were closed, head thrown back and her mouth opened wide as she continued riding my cock like a true blood cowgirl.

Between her moans and my grunts of pleasure we talked.

"Why are we doing this?" She sighed as she felt something familiar in her groin building up to its completion.

I groped the cheeks of her ass and sucked on her left breast, nibbling her enflamed nipple in the process before I replied, "Because we want to." Then I continued suckling her breasts like a hungry child. I alternated between her breasts and from nibbling to licking and sucking. While all this happened I remembered her telling me one time that she didn't breastfeed her children. The memory flashed through me as I continued sucking and fondling her boobs. No wonder, I told myself, that her breasts still felt so whole and not saggy despite she already having three children.

Then, out of nowhere, she summoned strength unimagined, she pulled my head away from her upright breasts and kissed me torrid. It felt like my lips and tongue encountered a vacuum as she sucked on my surprised mouth. I saw her eyes gleaming with a maniacal glint as her body shuddered from the force of her newest orgasm. She stopped from everything she was doing, just letting the sensation washed through her body.

"Ohhhhh. . ." Came her long satisfied moan as the last vestige of her orgasm emptied on my cock.

I let her be for a few more minutes then when she noticed despite all her hard work that my cock was still rocksteady, I smiled at her and said, "My turn."

Holding her by her legs anchored through my waist and her feet fastened on my back, I stood up. She gasped as she felt my manhood shoved a little further inside her cunt while I carried her outside the bathroom. Each step I took, specially when we ascended the stairs, enabled my cock to pumped itself in and slightly out of her still wet cunt. I felt like steam was enveloping the length of my shaft as I continued climbing the stairs then finally, depositing Cherry on the bed in their bedroom

Little adjustments with our position and I started fucking her for real. At first, I eased myself in and out of her in long, slow strokes. I wanted her to build up an orgasm anew. With my right hand, I teased her clits as I continued fucking her with a slow, steady tempo. Then, I accelerated a bit with both of my arms now supporting my weight (both hands cradled her head) as I quickened the pumps. Not exactly going jackhammer, but I changed my pace for her pleasure. I withdrew my shaft from her cavern in a slow stroke then when it's just my cockhead that was left embedded on her cunt; I swiftly pumped myself in with a sharp, vicious inward stroke.

"Bad boy!" She exclaimed as she felt another surge of orgasmic buildup coursing through her.

"Ohh, AH! Ohh. . AH! Ohh, AH!" Her mouth alternated from slow moans to quick, sharp groans as I continued fucking her.

Finding myself at home after a few more pumps, I took the liberty of adjusting again our position. This time, I took both her legs and draped it on my shoulders. This provided more pressure on my cock as her cunt tightened. On bended knees, I resumed pumping in and out of her with a pace Cherry's very familiar with. One time I couldn't sleep, I heard her moans as her husband fucked her on exactly the same position I was doing to her now. I held to her knees as I plough on and felt more excited when I saw Cherry's breasts swayed with each thrust I made. I was pumping nonstop now, already reaching the ten-minute mark (I don't know for sure because there's no clock or watch nearby to check but it sure felt that way), and sensed that it was my turn to explode.

I told her so and she replied, "Go on. I am too."

I said I would withdraw when I'm about to explode but she said no. "Do it inside me", she insisted.

I knew it's just a matter of seconds and I let go of her legs which she quickly enclasped around me. It took me by surprise because I realized she really meant it. She wanted me to fill her in with my cum. I suddenly thought I might get her pregnant and the mere thought was more than I could bear. With one strong pump, I exploded.

When she felt the warm jet of my sperm inside her, she cummed as well, our mixed love juices brimmed and dripped from her cunt to the bed. It felt so warm, our cum as it flowed.

"My god. . ." Cherry exhaled as her toes curled through the last throes of her orgasm.

I stayed on top of her as my cock gradually relaxed and naturally withdrew. We stayed on like that for several minutes. Her legs still holding me by my waist. Then she reached for my face and kissed me tenderly.

"Nice. You feel so good." I whispered to her as I disengaged and lay down beside her. She looked sideways and pinched me on my arm.

"You naughty boy!" She said while her eyes danced with the lingering sensation of lust.

"I couldn't help it, Cherry. You're irresistible and I would admonish myself if I let go. If you had declined, fine. Fortunately, you like it as much."

She didn't expect I would be straightforward. She later told me she was expecting I would sugarcoat so I could do a second round. I told her I wouldn't dare. She just smiled and she took her bath for the second time that morning. We both knew we'd be late for work that day but it didn't bother us that much. While having breakfast, I remembered and took my courage to ask. "Why did you let me cum inside you?" Cherry just shrugged and told me matter-of-fact I shouldn't worry. She's on pills and it was her safe period when I raped her. I smirked and she smiled naughtily. I then asked her the next question, "Why did you let me?"

Her face got serious and she explained she knew I have the hots on her and for weeks upon that realization, she couldn't let go of her imaginations. Cherry admitted she got intrigued and every time she thought of us having sex she would be wet. Of course, being married with three kids, she didn't act on her wet, wild daydreams. By the time I grabbed her earlier that day and kissed her, she confirmed her suspicions about me and she went with the flow.

Thinking in retrospect, I realized she was telling the truth. Even though she was flirting with me through and through, she never gave any incentive for me to act on. She, herself, knew the boundaries and would immediately stop when her flirts with me is reaching a certain level.

She held my arm when she noticed my silence as I brooded and told me this to comfort me, "Don't think of it too much. We both like what happened. If it happens again, fine. But we're both adults. Now that we know what it feels like, what's next is up to us."

As my answer, I kissed her again and casually told her, "Cherry, let's do it again."

She looked me in the eye then replied, "Fine but make it quick. We're late."

I didn't expect our second tryst would commence right away but what she told me was music to my ears. Another good thing was, she's not wearing her jeans yet and I wore slacks. I led her to the sofa and I told her go on all fours. I pulled her panties down and did the same for my slacks and brief. I briefly and gently prodded her still swollen cunt with my cockhead. When I found her entrance, I wasted no time and pumped inside her. She was holding to the back of the sofa while bending. I was fucking her from behind, dog style.

"You're really a naughty boy, aren't you?" She said in between her moans.

Knowing we're running late, I wasted no time. I unbuttoned her blouse and freed her breasts from her bra. Thank goodness, she wore a bra that time with a front clasp. It made it easier for me. I really love seeing breasts swaying as I pumped. Holding her by her waist, I positioned myself so I can pumped her continuously while I still have the liberty of watching her breasts sway to and fro. Then, prompted by her moans, I knew she's reaching her climax so I grabbed both breasts and tweaked her nipples as I jackhammered her from behind.

"Oh, it feels so good. Agh. . . Ahh!" Cherry had cummed again.

I have something else in mind. When I felt it's my turn to explode, I withdrew from her and told her to sit on the sofa. Still reeling from her latest orgasm, she meekly followed. When she was already sitting on the sofa, her face level with my flaming, hot cock, I shoved it in on her gaping mouth. It went deep and she gagged reflexively but I held her head steady and she couldn't disengaged. She realized I would mouthfuck her so she just adjusted accordingly. I pumped in and out of her mouth with shuddering pleasure. With a savage smile, I shoved my cock deep down to the base of its shaft and I cummed. Hot, gushing sperm flowed down her throat. I held her firmly and I could hear her moan, groan and gag. When I thought I was done, she suddenly grabbed my cock by its shaft as I slowly withdrew from her mouth. Her other hand grabbed me by my butt cheek and motioned me to continue. When I wouldn't, she started jacking me by the shaft as her mouth and tongue worked on the head. Feeling a bit disoriented from my recent explosion, I let her be. She continued her ministrations and we could both see my cock glistening with the combined juices of our lust and her saliva. I was almost grunting when I felt a familiar sensation starting with my balls. Cherry noticed this and she worked faster. This time, she sucked my cock from top to base. Then with one last flick of her tongue on my cockhead, I cummed again. My rich, thick sperm spraying her on her face.

Afterwards, she naughtily swiped her tongue around her lips like a kid wanting to save every ice cream on her mouth. Then she stood up, kissed me quickly on my lips and said, "You got your second round, you naughty boy."

She picked her panty from the floor and proceeded to the bathroom to wash and compose herself. I settled on the kitchen sink and brushed my teeth. A few minutes more, we're both dressed and ready to go.

So started my affair with Cherry.