Holiday Of Surprises

This is my first story in English. As the reader may notice, English is not my first language, so please be gentle, still all feedback is appreciated.

The story is quite short, but there may be another part coming.

*

I look at my naked self in the bedroom mirror.

"What's wrong with me? Why do all attempts to form a relationship with the opposite sex always go wrong?" I ask my reflection and try to see the answers in my image.

Somebody once said that the answers can often be found in the mirror. I can't see them.

It's been over five years since my messy divorce, and that marriage left me with only bad memories. We had been together for over ten years but left me with nothing. I don't have children either, even though we tried for years. Over the past two years, I've been dating again. I tried to form a relationship with two men, but both ended fast. I broke off with them after men revealed their true nature.

I am a 40-year-old, ordinary-looking woman. My name is Janita. I'm certainly not a beauty, at least not in my opinion. I'm short, and extra fat has accumulated in my butt and belly, but men still notice me and even compliment me. I have also been told that sex with me is fantastic, and I am aware that I am very open to experimenting and generally open person in the field of erotica. I have a vivid imagination, and it's been a good thing this year since no man has been in my bed for quite a long time.

"Am I still too easy or just too demanding?" I keep looking for explanations, but the mirror won't tell me anything.

Maybe I am a little bit too easy, especially when my desires become too great, but now I've been alone again for several months.

"Or is it almost a year?" I ask myself as I squeeze my breasts, which look okay to me. At least they are big; I smile at my reflection in the mirror. God, it would feel good if someone were to touch them.

I shake off self-pity from my mind. I get dressed and take the tram to the city center. I have a date with my best friend at the coffee shop, and I don't want to be late. My friend Sonja has been my support and refuge throughout my adult life, and I have always supported her to the best of my ability.

Sonja is married to precisely the kind of asshole I've encountered myself in recent years. Her husband Jared, who is not only a workaholic, is also a weekend drunkard. Sonja does not seem to understand this, even though we have discussed it many times.

Sonja and Jared have a son, Jon, who just turned 18. Jon is from a completely different planet than his father. He is an excellent student at school and enjoys astronomy. I bought him a telescope for his last birthday, and we went to see the stars together that same evening. Jon was so proud to show me what he knew about the stars.

I often worry about Jon, who, as far as I can see, is afraid of his father, and the sensitive son suffers visibly from the behavior he must face at home. Even at school, he has been bullied throughout the years. His father thinks he is weak, whereas I see a strong young man. I believe Jon is ahead of his peers in many ways, but his social skills are underdeveloped, and he prefers to bury himself in the stars rather than spend time with friends, which is what a boy of that age should do.

I arrived at the café on time and was about to order coffee for us when I noticed Sonja coming from the opposite direction, half a run.

"I wasn't late, darling?" Sonja asks, kissing me on my cheek and giving me a firm hug.

"Not at all. I just arrived myself." I take Sonja by the hand, and we move on to the only free table.

"Lovely to see you. It feels like it's been an eternity since we last met." I confess to Sonja.

I've missed her, but we've both been so busy that we haven't had time to meet.

"It's been busy lately, but it's wonderful that we are now starting holidays. We could meet every day." Sonja smiles.

"What do you mean every day?" I ask, a little puzzled because even though we are good friends and I have time to spend with Sonja, she is kept busy by her husband and Jon.

"I have a proposal for you, my dear friend," Sonja says, looking at me with a big smile as if she can't hold in some big surprise anymore.

"Well, tell me." I encourage her. I secretly hope that Sonja has finally decided to leave her husband. That won't happen.

"Would you like to go on holiday with us to sunny beaches? Just a week's vacation. You wouldn't have to pay anything for accommodation or travel. Jared's mother was supposed to go with us but had to cancel, and the ticket can't be refunded." Sonja says with excitement in her voice.

"Who are we exactly?" I ask skeptically. Will your husband come too?" I continue with a disappointed tone in my voice. I remember how their trip to Italy last year ended with Jared. Sonja and Jon returned alone after Jared was arrested in a fight.

"Yes, he comes too," Sonja confesses, and I press my gaze. We have never gotten along with Jared.

"But Jon is also coming, and Jared has promised not to drink this time," Sonja assures.

"Do you believe him?" I ask skeptically.

"He promised. We have talked a lot about this. We need a family holiday, and Jon suggested you join us instead of Grandma. Then Jared and I would have time alone." Sonja sheds light on her thoughts.

I smile when I hear what Jon has suggested. The boy has always been close to me, and hearing his suggestions pleases me.

"Is it a family holiday if Mom's friend goes also?" I Ask.

"You are family. At least for me, Jon and Jared didn't resist the idea either." Sonja assures.

I lean on the back of my chair and taste my coffee for some time to think.

"Well, if you've talked about it with the whole family, I guess I could go. I've been thinking for a long time anyway that I need a break from everyday life." I answer after a little while.

"Besides, I haven't even had time to spend with Jon lately, even though the boy has often asked me to come and visit," I answer Sonja as I notice that I have decided to go along.

"I know. He has asked about you often." Sonja laughs.

"So maybe we should have a glass of wine to celebrate the upcoming holiday and then go shopping. We need new clothes for the trip." Sonja suggests, clearly satisfied. I smile at my friend's enthusiasm.

Only two days had passed from our week-long holiday in the stunning scenery of the Costa del Sol when Jared's promise not to drink broke. We had just returned from a shopping trip with Sonja and Jon when Jared came to meet us in front of the hotel. He was drunk. The expression on Sonja's face was revealing, and she didn't dare look me in the eye, although she knew I wouldn't blame her.

Seeing his father, Jon immediately moved behind me, and I understood the hint. He didn't want to witness what would happen next when her parents would start arguing.

"Jon and I are going upstairs," I told Sonja, took Jon by the hand, and guided him past his father.

"Right, take that crybaby for a nap." Drunk, Jared said as we walked past him. I looked at Jon and saw tears in his eyes.

"Fucking whore!" Jared said to me as we walked through the hotel door. I squeezed Jon's hand as we entered the elevator. He pressed himself against my shoulder as the elevator jerked upwards.

"Never mind. You know what your father is like. Your mother can talk sense into him." I tried to convince Jon, but at the same time, I knew I was lying, and Jon was the last person I wanted to lie to. I kissed the boy's cheek, and he smiled lightly.

"Yes, I wouldn't mind if those two move to a different hotel or go home." Jon sighed in reply. He tried to be brave, but the expression on his face said otherwise.

I escorted Jon to their room and said he could come to my room if the need arose. My room was so small that I didn't want to invite the boy there immediately, but I felt the need to give him the possibility.

"Couldn't I come right now?" Jon asked pleadingly.

"Let's wait and see what those two decide. Your mom wants you to wait for her, so let's see where things go." I try to assure Jon.

Jon opens the door and walks into his room, looking depressed.

I close the door to my room behind me and sit on the edge of the bed with a sigh. The holiday had started great. Sonja, Jon, and I had already visited the shops at the airport and laughed together. Jon was sitting next to me on the plane, and we had already planned things to do together for the coming days. At least we were going to go and see the stars, with the help of a telescope I gave Jon as a gift, and we had to go swimming as well. In addition, there were plans to head to a nearby island for a night or two. However, it looked like a drastic change in plans could happen.

Jon had been overjoyed to hear that I was taking part in the trip. The boy's enthusiasm had amused Sonja and me, but he caught us along with his joy. Now and then, we had walked hand in hand, or I had held him by the arm, and kisses had been shared in the name of friendship.

Jon was already taller than me, and it was clear that the boy was rapidly developing into a young man and a handsome one. Fortunately, his temperament had not yet become defiant, probably due to his father's tyrannical behavior when drunk. I hoped it would never happen. Jon was very submissive and sensitive. I should be careful about my behavior around him to avoid breaking a sensitive young person.

I had just finished putting on a clean top and a new skirt I bought when a message from Jon arrived on my phone.

"Shall we go stargazing? I want to show you how the telescope you bought works." Jon wrote.

I smile when I read the message. Jon has moved on from the events downstairs.

"Sounds great. What time are we leaving?" I reply to Jon.

"At eight. We can walk to the hill behind the hotel." Jon answers.

"OK. See you downstairs." I reply.

I still have an hour before leaving, so I decided to rest a bit.

About two hours later, Jon leaned to me and showed me how the telescope worked. Jon chose a place for us, on top of a hill, and a bright starry sky opened before us. The air had cooled. The atmosphere was peaceful, and previous events at the hotel had already been forgotten.

The boy's enthusiastic behavior amuses me as he huddles around me, but I don't stop him, even though he sometimes seems glued to me without a purpose. It feels wonderful to be with him. I'm proud of how I can offer Jon this moment and a way out of his father's influence.

I glance at the clock at one point, as the evening has already darkened completely.

"Jon, maybe it's time for us to head back to the hotel so we don't get lost in the dark," I say to the boy, adjusting his telescope again.

"Yes, maybe we need to leave, but can we come again before we go home?" Jon asks, looking a little disappointed.

"Of course we can. This is wonderful." I answer honestly.

We pack the telescope and start to descend the path leading to the hotel when suddenly Jon cries out in pain and gets down on his knees to hold his calf.

"What happened?" I ask, terribly frightened, and rush to him.

"Let me see." I can't really see well in low light, so I dig my phone out of my bag, turn on the light, and put the phone down next to Jon.

"Sit down on that stone, and let me look," I say when I take off Jon's sandal. Jon sits down on a stone and stretches out his leg.

"I can't see anything here," I say in a soothing voice, examining the boy's leg.

"It felt like something bit my leg." Jon describes his pain.

"Where does it hurt?" I ask while I try to examine his foot in the poor light.

"The calf hurts," Jon answers. I bend forward and massage the calf; I can't see anything resembling a bite.

"I think you got a cramp. You've been drinking too little, and you should have put on those trousers anyway, not this swimwear. The air is already getting chilly." I say to Jon.

I feel the foot from the ankle to the calf and brush the skin to calm him down.

"Does this help?" I ask and focus on nurturing Jon. I continue to massage the calf gently.

Suddenly, Jon shivers and an involuntary sigh comes out of his mouth. I lift my gaze from his leg and notice how the front of Jon's swimming trunks is bulging, and a damp, round spot appears in front of the trunks.

At first, I don't quite understand what's happening until I see pulsation in his trunks. Oh my! Jon is ejaculating. Understanding it creates a massive feeling of satisfaction, and I smile, but I decide to act as if I haven't noticed anything. Jon pulls his t-shirt in front of his trunks when he notices I have fallen silent.

I lift the top of the blouse myself when I realize that he has had an unrestricted view of my breasts. Embarrassed silence descends between us until I am forced to break it.

"Well, I feel like we're ready. Would you try walking?" I ask Jon as I get up and fix my top. Jon gently stands up, covering the bulge in his trunks.

"Yes, much better. It doesn't feel like pain anymore." Jon says, kissing me on my cheek.

"Thank you, Janita. You're the best."

"You're welcome. Now, let's walk cautiously back to the hotel. Let's both shower and eat." I replied, taking Jon by the hand and walking to the hotel.

The boy must also clean his trunks; I laugh in my mind.

When I get to my room, I sit on the bed and think about what happened. Events already make me smile. Was it Jon's first orgasm? Did he understand what was happening? Of course, he did. He must already be masturbating, I reason. I was pretty sure he never had a girlfriend, though. I find myself recounting the event in my head. The situation was somehow strangely innocent and intimate, I say to myself, and the thought makes me feel relaxed. I take off my clothes and take a shower.

After showering, I wrap a towel around me, and when I step out of the bathroom, I hear my phone vibrate, signaling an arriving message on the bedside table. When I picked up my phone, I noticed Sonja texted me about tomorrow's schedule.

"Thank you for helping Jon and taking him to see the stars. He went to bed, already satisfied. You are the best friend ever. Tomorrow, we will go to the islands."

He went to bed satisfied. I smile at the thought and start answering.

"So you managed to settle things with Jared. See you tomorrow. You are the best." I respond quickly to Sonja.

She is always so thoughtful; I smile and pour a glass of wine for myself. I thought this had been a hard day when the phone vibrated again.

Well, what now, I think? I picked up my phone and noticed a message from Jon. It's a picture message. Without further thought, I tap the message open, and the wine glass almost falls out of my hand.

The boy has taken a picture of his bare, erect penis and sent it to me. Below is the image he has written.

"I thought you'd love to see what you accomplished."

The picture causes a strong and wide range of emotions, from fright and guilt to flattery, but I can't take my eyes off the picture. Jon's penis is so beautiful. Maybe about 4 inches, slender and straight, standing directly against Jon's flat belly, reaching towards the navel it couldn't touch yet. He clearly took the picture in secret, under a blanket.

My stomach is pounding, and my mouth is dry, and I can't help but confess to myself that I am aroused. Image of the wet spot in Jon's swimming trunks a couple of hours earlier, and I see in my eyes how that beautiful organ had spit out a small amount of nectar from its tip because I had rubbed his leg and unknowingly offered sight to my breasts. I sigh deeply.

However, I can't get involved in this game and should end it now. For too long, I wondered how I would react to the message when the phone vibrated to signal a new message--another post from Jon.

"Please don't get angry. If you get angry, don't tell anyone. I didn't mean any harm, but when it happened when you touched me and let me look at you."

The boy was panicking. He thinks I deliberately gave him a view of my breasts. It makes me smile. Jon is just cute. I'll start writing an answer.

"I'm not angry, but you can't send me pics like that. I won't tell anyone about this, don't worry. Now go to bed." I formulate my answer.

Neutral, in my opinion. I don't want to be rude or hurt Jon's feelings. Which, judging by the picture, are now bursting into a storm. It didn't take long for the phone to vibrate again. I lean on the headboard over the blanket, wrapped in a towel, trying to organize my thoughts, which are not clear.

"Do you like it?" A short message with a heart emoji reads.

Oh no, I sigh out loud. I had somehow encouraged him, even though my intention was the opposite. I can't help myself, and I open the picture again and stare at it mesmerized. After a while, I notice that my fingers are getting between my legs, and I rub my pussy with Jon's picture open on the phone. I'm already wet. The phone vibrates again.

"At least answer something." Jon writes. I now wonder how to respond, but my body already knows it.

"It's a lovely-looking penis, Jon. I like it." I write with trembling fingers. I pressed the send button. I regret it immediately, but the gate has now been opened. Involuntarily, the amount of fluids in my pussy increases.

"Wow, wonderful. I thought you wouldn't like it." There is a kiss emoticon at the end of the message.

"Yes, I do, but now you need to start sleeping. Tomorrow, we will go to the islands and enjoy the holiday together." I reply more cautiously, at least in my opinion.

"You're so hot... I want to go with you tomorrow alone. Good night." Jon replies, and I lean against the headboard.

I encouraged him again, even though I didn't mean to, or did I? I am completely confused. At the same time, the thought of Jon and the two of us spending the night alone made me feel even more aroused. Although the idea is impossible, I could give myself an orgasm with that dream. I open Jon's picture again and imagine touching his penis, taking it into my mouth and pussy. I have never dreamed of such a young man, and just the picture and the thought of it made me orgasm intensely. I guess I'm going crazy. Hell, this is so forbidden.

The alarm clock wakes me the following day, tearing me back into reality from deep sleep. I wake up naked under the blanket. I'm sweaty after a restless night. I came twice in the evening with my fingers and Jon's picture, which must have plunged me into a restless night. I needed the orgasm. The exchange of messages with Jon comes back into my mind vividly, and I can't help but reread the messages. What have I done? What am I going to do about it? The questions run through my mind, but my body's opinion is evident when I look at the picture Jon sent me again. No, I can't. I toss my phone on the bed and take a shower.

After a shower, I pack lightly because I plan to spend a night or two on a nearby island to enjoy the sun and beach life. I close the door to my room and head downstairs for breakfast. When I arrive at the restaurant downstairs, I notice that Sonja, Jared, and Jon are already sitting at the table. I am forcibly drawn to Jon, who stares at his plate and vaguely spins his spoon around the food. The boy looks depressed. I wonder what he thinks of yesterday. I find myself excited to meet him. I start walking briskly towards the table.

When he notices me, a smile spreads across Jon's face.

"Good morning, sleepyhead. Did you sleep well?" He asks when I arrive at the table.

"Thank you very well," I reply with a smile.

"Am I late?" I continue, looking at Sonja.

I look at Jon with new eyes but can't define how I see him now. More mature than I expected or assumed.

"Not at all. We, too, just arrived, and our belongings are already packed for the island adventure." Sonja replies happily, but I notice fatigue in her features.