Arriving home early, I was greeted by the sound of squeaking bed springs. On route to my own room, I caught a glimpse of a woman on top of him through the open door. They were too busy having a fuck to notice me, as I quietly slipped past them. The scene in the neighboring room put a damper on the excitement of the gift I bought myself.

Feelings of self-pity washed over me, as I reminded myself how I landed up in this situation. It reminded me of Dad's divorce from Mom when I was sixteen years old. Back then, I made an obvious decision to move in with Dad. In the beginning life was good; Dad had money from his semi-legal, gray business. When I started to work, independently from Dad's business, Dad sold me the idea of buying a house with him. The money kept on rolling in, and we prospered financially. We lived together sharing costs with financial benefits for all three of us.

Where the problem came in, that neither me nor my brother could have a girlfriend. We had to follow Dad’s dogma of ‘fuck then fuck-off’. It was a dogma where loving relationships were frowned upon. A dogma where having a relationship with a woman was a bad thing. A dogma where screwing a prostitute was the norm. No complicated relationships, no buying of flowers or chocolates, none of that romantic bull. You screwed your – or his – whore, paid your due, and that was it. No strings attached.

I never screwed whores, not a ‘fresh’ one, not a ‘used’ one. I craved that romantic link. I craved to have the same female company for years. I wanted to have a full-time, financially free, relationship. I wanted a girlfriend.

I couldn’t have one, as she would have been ‘shared’. Alternatively, I could have had a secret girlfriend, secret from Dad and Brother. This secret girlfriend wouldn’t visit me. She wouldn’t call, she would be like a mistress. Which girl would want a boyfriend like that?

A knock on my door broke my thoughts, as a strange female voice asked, “Honey, would you like some good loving?”

“No!” I replied sternly. They must have heard me coming into the house.

“C’mon, honey, I’m fifty percent off,” she tried to lure me in with the price.

“I said no,” I replied, with a sense of annoyance in my voice.

“I told you he’s a weirdo. Come, let me take you back to town.” Dad answered her loud enough for me to hear.

I shook my head and reminded myself of the little present I bought myself. It was a weather predicting wrist-watch. The little device had a built-in barometer, along with some other features that I didn’t care about. Excitedly, I unpacked it and charged its batteries. As I waited, I read the owner’s manual. There I discovered that it was a damn fitness watch!

Batteries took a long time to charge for the first time. I used that time productively by dropping my trousers and underwear. I grabbed my flaccid penis and slowly started to massage it. I slowly started getting hard, and it turned into an intentional masturbation exercise. This just proved the point on how badly I hated whores. I chose to play with myself over having sex with a prostitute.

Over several days, the watch manufacturer’s website nagged me to join their partner. Their partner was a calorie and exercise counting website, which I joined purely to suppress the annoying, woman-like nagging.

Something strange was happening to me; I actually participated in the weight-loss program on offer. I even bought both food and bathroom scales. As I was a math geek, the numbers drew me in; however, statistics were not my strong point. From my initial inputs, the algorithm declared me as ‘obese’. I hated that term since I considered myself only as ‘over-weight’. This little home truth hurt.

On the website, I even made few friends that were supportive. They commented on my good days; they encouraged me on my bad days. We were a little community in cyber-space. Actually, I enjoyed that human interaction, even though it was on-line.

The watch was also playing its part. I discovered that there was some sort of a target for walking. This feature was unknown to me until I ‘accidentally’ stepped over the step target. The watch gave a strange buzz, I looked to see what was happening. It displayed a cute animation which raised a smile on my face.

I investigated these targets with a geeky curiosity. It turned out that the goal kept on moving, thus encouraging you to log those steps. These was achieved either by walking or running. There was a third method: it involved a rapid movement of the wrist that stimulated a certain body part.

~~~

I continued to log my food and weight on a daily basis. I became good buddies with my on-line friends, as all of us were taking the same journey. In the messages section of the website, a newbie post caught my eye. Something compelled me to make a friend request, which she accepted.

As with the people who helped me, I set her up and got her settled in into the site. I watched and guided her, as she begun the journey to a healthier body herself. I congratulated when she did well; I encouraged and consoled when she made dietary mistakes. Slowly but surely, she came out of her shyness.

Since she was from the same metropolis as me, we started chatting over more private social media. As with the weight-loss website, we were drawn to each other's personalities. We were beginning to develop a friendship; a clean friendship, there was never any sexual talk on-line. Slowly, we started to confide in each other, despite not even sharing a picture of what we looked like.

One day she made an unexpected move, when she asked to join me on one of my hikes. I was both surprised and delighted at the same time, as I eventually got to meet Melissa. We were going to meet in person after four months of an online relationship. Excited to meet her, we made the necessary arrangements.

~~~

I parked my car under the many small, sparsely growing trees. The nature reserve’s car-park respected nature, as they layered large gravel stones to make a surface to park on. The parking bays were delimited by large wooden dowels. These bays were arranged around the trees in a haphazard fashion.

Towards the stream, the trees were much older and much closer together. On the other side of the stream, the council built a dozen or so picnic spots. Each one of them was equipped with a self-service fire pit and a concrete table with benches. That day, there were about three families enjoying a meal al fresco.

I watched a car pull in and park in one of the many open bays. The driver was a tall, skinny bearded man wearing a pair of jeans and a black-and-red checkered flannel shirt. His passenger was a rather roundish, brunette with plump, rosy cheeks. She was sporting a white T-shirt, a denim skirt and a pair of sneakers. Dad’s prostitutes would be ashamed to wear makeup the way she did. She looked hideous.

I watched as the man dialed a number on his mobile telephone. This nature reserve, being a little urban oasis, had good signal coverage. I observed him getting a dial tone, as my mobile began to ring. It was an unrecognized number which I didn’t answer, as I knew that it was them looking for me.

“Hello, I’m Jack Kowalski. You must be Melissa Swarthøvn. Nice to meet you,” I introduced myself to the round, young lady.

“Yes… yes, I am,” she nervously strung a reply together.

“Hi, Jack,” her tall companion introduced himself to me. “Jack, I’m Doctor Simon Nussbaum…” I got an annoyed look on my face which he clearly picked up on.

He continued, “… darling, before you get all hissy, allow me to explain. I have been treating Melissa over here for the last eight months. She had some major trouble earlier in her life, and turned to food. Now, with the help of a charity organization, she is finally getting both psychological and dietary assistance.

“My reason for being here is to support Melissa. She doesn’t get out much, and the people in the gym are horrible towards her. She looked with jealousy at you; at the fact that you get to do all this hiking while she’s stuck in the smelly gym. I challenged her to ask you out. I needed to push her. Eventually she did it, on her own. Then she got cold feet and wanted to back out. If I didn’t come with her, you would have been stood up, darling.”

I accepted his explanation and got the hike going. I understood where Melissa was coming from; I have been in her position myself, where I was the social outsider. For people like her, it was simpler and easier not to socialize.

We used a wooden bridge with no railings to cross the stream. As we moved across it, I could feel every footstep that Melissa made, as the bridge bent and rebounded under her weight. Behind her was Dr. Nussbaum, whom I imagined losing balance and falling into the stream.

The gravel path made a left turn towards the picnic sites. We carried on straight into the open grassland along a dirt path. The autumn grasses were about a foot high and of a dry yellow color. We transitioned into a more wooded area as we headed for the hill.

There the path climbed up one of the valley sides. After a short while, we reached a bit of a level path and needed to stop the hike. There was some heavy breathing going on behind me. Melissa was already out of breath. Shade was not hard to find among the sparsely populated acacia trees.

We pulled off the path as we heard repeated “Excuse me! Coming through!” We all saw three middle-aged men approaching us very rapidly. The sweaty men simply ran past us and continued running until we lost sight of them. As they raced through, they gave us a simple “Thank you”. We were all stunned at the fact that it is possible to be this fit!

Melissa recovered; we carried on with our slow walk through nature. The path took us up to the top of the hill, where we took a break to admire the view of the city. Once again, we needed to rest Melissa, for she was in such poor shape.

The route was a circular one, with the path up being different than the path down. We got to a tricky part where two huge outcrops caused the path to descend by means of switch-backs between them. The path was steep, and the designers incorporated uneven steps on the straight sections. The turns were lined with gravel to minimize slipping on mud. Trees grew on either side, providing hand-holds for those not-so-stable on their feet

I inched my way down the sharp, tight, left hairpin. I used the acacia tree as a hand hold as I baby-stepped down. I made it down to the relatively level section of the path. The path already walked to the switch-back was now on my left, and a good four to five feet above. The path after the next switchback was on the right with a drop of about twenty feet.

Melissa then attempted the descent. She chose not to grab a tree for support. She stretched out her arms for balance as she took her steps. Her stride was too long for the conditions. She lost her balance, and stumbled. Her momentum took her to the edge of the path, where it gave way under her. She fell backwards and almost slid completely off the path.

A young, flexible tree caught her early, albeit in a compromising position. A branch had gone up her skirt, along the outside of her leg. Its thorn got hooked on her waist strap of her panties. She frantically panicked as the tree was giving her a type of a wedgie. Somehow, she managed to throw her other leg onto the path. With her legs wide open, I got a view of her crotch. Despite it not being a polite to look up a girl’s skirt, the focal point was her faint tell-tale wet spot.

I helped her to roll onto the path. Since the roll was quite desperate and violent, the branch stretched her underwear elastic to a point of no return before it tore from the tree. That made her panties virtually useless. She tried to keep them on regardless, by folding the panties over the top of her skirt.

Just back on her feet, she lost her footing again. This time, she body-slammed into me. I used that opportunity to give her a gentle hug, which she seemed to accept. In the embrace I calmed her nerves, and allowed her adrenaline to settle down. As she moved her body to get a better hug, her panties got untucked from her skirt, and simply slid down to her ankles.

I bend down to retrieve them for her, not risking another fall by her. I maneuvered her legs myself making sure that I touched her calves. I couldn’t help myself but verify the wet spot I saw earlier. I handed the damaged undergarment to the owner pretending as I have done it before.
 
“Ohh, I see someone liked that,” the ‘Toothpick’ started to look for trouble.

“Someone got a boner,” he carried on taunting.

“Oh, shut it,” I retaliated with a sense of annoyance.
 
“No, no, it’s good,” the shrink tried to defend himself, as I got the hike going again.

“How can that be good?” an irritated Melissa chipped in.

“Melissa darling, you are now old enough to be considered as ‘sexy’,” the shrink continued, “as I told you in therapy, you need to embrace your sexuality.”

“Jack, you must have felt something,” he turned his argument towards me, “otherwise you wouldn’t have had that boner.”

“There wasn’t anything,” I barked.

“Oh, come on, Jack.

Don’t give me that,” he continued to push the issue.

“I think looking up my skirt wasn’t enough for him. Touching my legs and panties finished him off,” the ‘round’ one pitched in.

“I’m sorry, Melissa. I’m sorry to have looked in your compromised position,” I tried to defend myself without hurting anyone.

“Did you… did you at least enjoy what you saw?” Melissa’s attitude suddenly changed direction. I could sense a smile forming on Dr. Nussbaum’s face.

“Well… Jack?” she pushed the issue as I didn’t answer her.

“Well, I do enjoy a good up-skirt. You gave me a bonus; you had a wet spot,” I went for broke. The gloves were now off. I had to lie little as not to hurt her feelings.

“What wet spot? There was a wet spot?” she panicked.

“Now, now, darlings, play nicely,” the peanut gallery commented.

“Shut it!” we both simultaneously told the doctor off, giggling afterwards regarding the timing.

“Oh? So she also got aroused? That’s wonderful, Melissa!” the shrink was now on her case.

“My condolences for having to deal with him,” I mockingly told her loud enough for him to hear me.

“Yeah, he gets his mood swings,” she sarcastically replied.

“Melissa darling, I heard that. You still haven’t told your doctor what aroused you earlier.”

“It doesn’t matter,” she defended.

“Oh, yes it does. I want you to be open about your sexuality,” he grilled her.

“Cut it out; if she doesn’t want to talk about it, then she doesn’t want to talk about it,” I cut in.

“Excuse me, darling, you are not the psychologist here!” the angered Simon raised his voice at me. I just laughed him off.

“Well, boys,” she had enough, “I was just wondering if Jack is circumcised or not.”

“Whoa, now that is below the belt,” I expressed my amusement and shock.

“Don’t you start!” she retaliated.

“Yes ma’am,” I mocked her.

“Well, Simon, you told me to be free and open with my sexuality. You told me to explore every opportunity. So here I am!”

“Melissa darling, yes I did, but that was a bit tad too vulgar,” the doctor counseled his patient.

“I’m sorry, Jack,” she apologized immediately.

“It’s all right,” I replied accepting the apology.

“So, Jack darling, how about showing your tool to the young lady?” he challenged me. I thought about the statement and hatched a plan. I stopped the hike, and handed my tool (a Swiss Army knife) to Melissa. She got the joke, while the tall one rolled his eyes.

“Melissa darling, why don’t you just ‘help yourself’ to his penis? I’m sure that Jack won’t mind,” he encouraged her to make physical contact with me. She looked at me with hope mixed with curiosity as I gave her a small nod. I stood with my legs slightly spread as she moved in for a touch.

From her body language it was clear that she wanted to touch, but didn’t know how to approach it. She was looking for guidance, on how to execute the touch without causing offense. I could see that she wanted to have a positive experience. I could see her eyes starting to become glazed, a tell-tale indication of her arousal.

“Do whatever comes naturally to you,” I whispered to her. That was the little push she needed. She approached me and placed her palm on the semi-aroused bulge in my trousers. She made contact through the trousers, but was nervous to do anything more.

“People coming,” Simon announced in an audible whisper.

I broke off the sexual contact, and got my hiking party on the move. We were beginning to hear sounds of people, of fires crackling and the smell of barbecued meat. We returned to the car park few hours after we started.

“Melissa darling, how was your hike?” he inquired of his patient.

“Tiring, exhausting, but good,” the happy sounding Melissa responded.

“Melissa, Simon, it was a nice experience. I think we should do it again,” I began to sign-off with them.

“Jack darling, I think you and Melissa have some unfinished business,” Simon surprised us.

“What ‘unfinished business’?” she queried.

“She hasn’t touched you properly. Why don’t you two come to my place and finish what was started?” Simon made us an offer.

I waited for Melissa to make the first move; she waited for me. The psychologist needed to resolve the stalemate. We both reluctantly agreed.

~~~

I sat on the couch next to Melissa, observing her reaction to my advances. I started by holding her hand, and moved on to running a fingernail up and down her forearm. I could sense that she was getting aroused, so I pushed her further. I got her to put her knee on the couch, and let the skirt cover her privates, as she was still commando. I traced my finger up and down the exposed part of her inner thigh.

I saw she was enjoying this attention from her fidgeting. I sensed her arousal from her breathing. My hand continued to make its way higher and higher up her skirt, but turning around few inches from her privates.

She re-positioned on the couch, almost lying down. I got her so aroused that she removed her top to expose her breasts. I got her to play on the top, whilst I handled her bottom. Her legs were spread, and I continued to stimulate her inner thigh

I re-positioned my hand to stimulate her clitoris, and the opening to her vagina. There, I ran my fingers up and down her wet lips redistributing the moisture. I made fast and small circles over her aroused clit, arousing her even further.

We saw that she was close to an orgasm, and this prompted Simon to organize a towel. With the towel in place, I picked up the pace. The two-handed effort begun to pay off, as she began to twist and squirm. I ignored her complaints of wanting to pee; it’s not pee that’s coming, it’s a wet orgasm. I carried on driving her throughout the squirting orgasm, retracting her over-sized clitoris’ hood to finish off.

Once I recovered, I didn’t let them touch me. It was a strategy to get them to come in a month's time for the next hike. I hugged both of them individually as I said my good-byes and left. I left her wanting, I knew she wanted to do me as well, but I didn’t want a one-night stand.

~~~

We kept on meeting up like that for the next year or so. Each month, Melissa kept on bringing a lighter and lighter body. I kept on complimenting her on the achievements. Her stamina kept on improving not needing as many stops. The incident site had a special significance for us, as without it we may not have grown as close as we did.

It became a tradition to go to Simon’s place after the hike, for ‘a shower’. As time went on, we performed more and more daring sexual acts with each other. Quite early on, we discovered that Melissa still had her hymen intact. We respected that, and never inserted anything in there.

Encouraged by Melissa, of all people, I tried a little non-penetrative gay action myself. I allowed the delighted Simon to masturbate me. The feeling was quite unusual, as normally I get the sensation from my hand as well. I returned Simon the favor by giving him a hand-job. In a strange way, it was enjoyable.

~~~
 
Eventually both myself and Melissa have reached our target weights. We allowed her body to recover from her skin removal surgery. Afterwards we embarked on a few, much longer hikes. Everybody was equipped with a first-aid kit after the lesson learned on the first hike.

I have booked and sponsored four places on a two-day walking, three-night group hike. It was a hike in a beautiful coastal forest, which included a several mile beach section. We were well prepared, with our equipment run-in and tested on a previous eight-hour hike.

The day of the big hike came, and we all were very excited. On the way there, we all realized that we wouldn’t have done any of this without each other. Although we had a ‘late entry’ into our quartet, we found that this fourth person added another dimension our group.

The night before we set-off, we slept in the open around a central fire. It was the height of summer, so the nights were quite warm. The expedition leader woke the group of twelve before sunrise. He wanted us to be ready to move out shortly after we witnessed that event.

We got up in high spirits, ate our breakfast and packed up our gear. We were waiting on the beach for the sun to rise. And rise it did, as it gave us a spectacular surprise. We watched the sunrise through thin cloud, dimming it sufficiently as not to blind. To everybody’s surprise, a crescent of the sun has risen. We have caught a partial solar eclipse on the day of our hike. Melissa felt compelled to kiss me on the lips for the first time; this caught me off-guard.

The hike was grueling, in hot and humid conditions. We took and clarified our water at every available opportunity. By far, this was the most physically demanding day I’d been through. By far, it was the most rewarding day too. I got to see a part of the country that very few people get to see.

That evening, we set up camp a few miles inland. It was on a cliff top, overlooking a waterfall. The area was wooded, but safe from anything that would harm people. I was exhausted, and so was Melissa.

At bedtime I climbed into the tent with Melissa. Simon shared his tent with a boyfriend that we found for him. They have been together for a few months and their relationship is flourishing. In our tent, a hot and genuinely sexy Melissa put her arm around me. We snuggled for a while and then she got some ideas. Her hand explored my lower regions, first through my clothing then skin-to-skin. I didn’t make anything of it, as that was her normal routine. I didn’t return the favor of running my fingers through her labia. She exposed my genitals as she usually did. She got me hard in the practiced manner and I settled in for a goodnight hand-job.

Melissa went a step further by getting me to fondle her breasts. I wasn't a breast man, but I complied with her requests. Once she thought that she was sufficiently aroused, she got completely naked. I ran my fingers up and down her labia, which showed her that I was interested in her. I played with her clitoris, then with her clitoral hood.

Her lips touched mine in a kiss, as she grabbed and rotated me on top of her. I felt my penis pressing against something, and later I learned that it was her clitoris. When she opened her legs, the signal is clear. I jockeyed for a better position and delivered what she has been asking for. I gently pushed in and feel the way blocked early on.

She encouraged me, as I pressed hard and broke through her vaginal seal. I was inside of her. My penis was the first object inside her vagina. She was the first woman, or man, that I had entered with my penis. The squeeze of her vagina was incredible. Every small movement sent a sensation of ecstasy. I proceeded to gently massage her insides with my penis. I must have been the perfect size for her, since on every stroke she reacted. I must have been stimulating her G-spot. She even allowed me to ejaculate inside of her. Once I removed myself from her, like a typical male, I fell asleep.

The second day of hiking was also physically grueling. During our twelve-hour trek, we crossed a small mountain range. The scenery, the bird-life, everything was so beautiful. Melissa was hiding the physical pain of losing her virginity pretty well. Nevertheless, she kept up with everybody and completed the crossing.

At the finish point, we slept our last night in the tents. I got to have sex once again with my girlfriend. This time around we had a better understanding of what we are doing. We responded better to each other. Both of us were more aware of what we are doing to each other. I actually got her to climax first. I held her lips open as she sprayed her fluids against the tent’s fabric door.

In the morning, our transport arrived to take us back to the starting point. What took us two days to walk, it took the driver three hours to drive. On foot, we took a direct route. The car needed to make a ‘U’-shaped journey, utilizing a mountain pass.

Once in our own vehicle, we confessed to Simon. Simon was over the moon that we managed to do it. He himself gave George his first sexual experience on the last night. We all returned tired, exhausted and happy.

~~~
 
Simon has specialized in obese psychology, and George is living with him. Dad is behind bars for possession of a banned substance, and for harboring an illegal immigrant. Brother made a few bad deals, and since then fled the country.

Melissa qualified as a park ranger, and now takes tour groups to see wildlife. We became a couple, and live in the bush close to her work. I finally got my pilot’s license and fly the shuttle between the park and the international airport as a part time job. When I’m not flying, I work part time for a software company remotely. Both Melissa and Simon now experience a penis uncut.