Helping Out My New Friend

"Really?" "Yes. Honestly. You can tell me, I promise I won't mute or block you or anything." I answered. It was obvious he wasn't sure if he should say whatever it was he had on his mind, or perhaps he was struggling to find the right words to use. It was a bit odd, after all we'd been chatting regularly for two weeks now, discussing some intimate and deeply personal things. For some reason however this was different, more difficult. The chat window remained silent for a while as I stared at it. He had sent me a private message a few weeks ago. A simple "hello", the sort of which I get about a dozen of each week. It was his second message which had caught my attention. "Would you like to talk? I don't care much about what, just want someone to talk to". Though less often, I'd get messages like this sometimes but I decided to answer how I'd love to chat about normal things. The next time he came online he whispered me and we started chatting. We talked about the weather, the news, food and movies, and to my great surprise he didn't direct the topic towards sex within ten minutes. Instead he showed genuine interest, and before I knew it it had become two o'clock at night.

In the following days we talked some more and got to know each other a bit better. He was 23, intelligent, kind, a bit naive and with a fairly good job in IT. He also still lived with his parents, and had no experience whatsoever with girls. The anonymity of the chatroom was the only thing which allowed him to even talk to me without turning red and starting to stutter. He had been raised overly protective and in a very restrictive and religious manner, his parents forcing him to come to their church up until a year ago, and he hadn't even been allowed an "evil" Internet-connection until his 18th birthday. He confided in me his lack of actual, real knowledge about many things. Most of what he knew was only theoretical, and he had many questions he obviously couldn't get an answer for from his parents. His true and uninhibited curiosity made me enjoy talking to him, explaining things and answering his many questions. I patiently explained periods and how it made me feel, what I talked about with my friends, how I experienced attention from men, and all sorts of things related to personal grooming, hygiene, hair and clothes. We shared some pictures, just normal ones from holidays and such. Things did however slowly get more personal and intimate. I talked about kissing, my first time having sex and how I masturbated. He had never even kissed a girl, only once held hands with someone from their church community his parents had set him up with.

The chat window was still silent, he didn't know what to say. I decided to help him.

"What's it about?", I asked.

"Well, about you. Or me, depending on how you look at it".

"Right. That doesn't really help..Did you do something? Is it something you feel you should or must say but you don't dare or want to? Do you feel guilty for not having done so earlier? Are you afraid I might get upset or angry? Something like that?".  This time he answered immediately, "Yes" it read. It made me smile, I had a good hunch what it was about and I decided to help him out, let him get it off his chest. "May I guess? Did you masturbate to my pictures?". It remained silent for a few seconds. I added "I don't mind if you did, really". This time he promptly answered "Well yes..actually I have ever since you sent them", followed quickly by "I sort of knew you'd be okay with it but I'm still glad you've said it is... but it's not really what I wanted to ask".

"Ok", i said, "Just..you know, say it. Nobody died right? Just tell me and I promise I will not get angry or anything".

"Right..well..". A short pause. "An", he said, "I think I've fallen in love with you and I really wanted to ask you if you would please help..well, do.erhmm... to lose my virginity..will you sleep with me?"

I was stunned, then heard myself say "Jessusss...". This I didn't see coming. A strange mix of emotions came over me. I was surprised and also not. Flattered, perhaps, unhinged. I didn't know what to say. A new line appeared in the chat: "I'm sorry..are you upset? Angry?". "No, no..not at all. Really, just surprised", I answered. "I'm touched you feel this way, but you know I can't be your girlfriend right? You shouldn't fall in love with me..". Again these strong, mixed emotions. I felt responsible, some pity perhaps, especially when he wrote how he knew all that but couldn't help it, it had just happened, he had never been able to talk to any girl for so long and about so many things. I didn't want to just say no, that didn't feel good, he deserved a better explanation. Fortunately it had gotten quite late, so I promised I'd answer by the next day and said goodbye. I pondered his question while brushing my teeth. Why did he ask me? Of course I couldn't, obviously. I mean, come on, sure we had shared many intimate things but still. Look, I very much want him to find someone special with whom he can be at ease, sure. But obviously that wouldn't be me right? I mean, why me?

The answered popped up, as a flash of insight. "Because for weeks now you've been letting him experience something which he has never before experienced and which he doesn't know how to find elsewhere". I stopped brushing for a moment. I should've maybe answered two or three questions and leave it at that, but I hadn't. I should've kept things in general terms, but I had made it much more personal, intimate even. Had I not maybe planted this seed myself, caused it to happen, maybe even steered it towards it? It took me a while to fall asleep, but when I did I knew what I would do.

The next evening he came online at a much later time than usual. Even before he said hello I could feel his tension, or was it mine? We briefly discussed our day as if nothing had happened before I decided to get it out. "I've thought about your question", I wrote, "Pretty long actually. Are you still sure it is what you want?"

"Yes, very much" he said. "Right..here's how it's gonna work. I will explain my proposal, you just listen. When

I'm finished I want you think about it for at least a few minutes before you say yes or no. Do we have a deal?".

"Deal."

"All right..so here's my deal. We'll go on a dinner date. We'll both pay for it ourselves,I insist on it. During this we will both decide if we feel comfortable with it. We agree upfront that if any one of us wants to call it a day after, the other will respect that. If we're enjoying ourselves, after dinner we'll go to a hotel. This is non-negotiable. You will make the hotel reservation. It does not need to be luxurious as long as its got a double bed and a bath. I feel you should experience your first real sex with someone really special, but I will make you orgasm and help you to make me too. I hope it'll help you to be able to be less nervous around women. The next day we will say our goodbyes as two people who shared something, and then you should find your own way further, because I can't become your long-term girlfriend. Think about it while I go and get some tea".

As I walked to the kitchen I felt a weird pressure, of tension and responsibility. I let out a long sigh before returning. His answered didn't come as a surprise, it simply said "I've thought about it, I really want to, and I promise I'll follow your rules".

... a few days later...

He stood up as I approached the small corner table in the back of the Italian restaurant he'd chosen. "Hi.. eh..hey..Anne..how erhmm.." he stammered as he held out both hands, his right a bit further than the left as if he couldn't decide between a hug and a handshake. As I held his arms and leaned in for a hug I gave him a quick kiss on his cheek. "Hello Dan, what a nice place you picked and how good to see you for real" I said as I sat down. We talked a bit more as we studied the menu, and it quickly became clear Dan had, indeed, never been on a date before. As we talked though he managed to relax a bit more, and after half an hour or so I could see him as he really was, or could be. He was kind, caring and intelligent, but lacking in confidence and full of doubt. "So...", I said as the waitress had collected the paid bill, "what shall we do? Would you like to go home or.......?". "I hmmm.. if you still want to..I mean..do you, you know..I don't wanna go home". "Okay then, let's go to the hotel?" I smiled as I stood up and reached out with my hand. We got our suitcases from our car, as it turned out we had parked with 20 meters of each other in the parking garage around the corner. I felt my stomach cramp, and a feeling of nervousness come over me as we walked to the hotel. Things were about to get real soon, and I had no idea how best to progress.

The room was simple, but it looked clean with a fairly large bed and a bathroom featuring a full-sized hot tub. We dropped our bags on the floor, and I quickly turned around. I had decided the best way was not to wait too long, it would make things awkward. I threw my arms around his neck, pulled him closer and kissed him. He seemed utterly surprised, for a moment just standing there before he closed his arms around my waist and pulled me even closer. For someone who'd never done it before he wasn't even bad at kissing. He went slow, and didn't try to shove his tongue down my mouth as some had in the past. We kissed a bit more, and after I had placed his hand on my behind he became a little more adventurous and started to feel and explore a bit. I let go of our embrace and let my hands slide down to his waist. "Why don't you check if the bath is clean, and then let it fill up? Then I can get some things ready, okay?" I said before he could speak.

He nodded and said "Okay". I could hear the tension in his voice still, I had to get him to relax. As he went into the bathroom, I quickly closed the curtains, turned up the heat just two degrees, and got some stuff from my suitcase which I put in the drawer of the nightstand. Some massage oil, lube, a vibrator and some condoms, after all it was always best to be prepared. Finally, I quickly took off my jeans and put on a simple skirt, which not only would be more comfortable but would help with other things I had in mind too. I lied down on the bed, and a moment later he walked back in the room. "I've cleaned it, and it's running but it'll be a few more min.....". He stopped as he looked at me, lying down on the bed. "That's great. Why don't you come lie beside me while we wait?", I said as I padded the bed next to me.

I pulled him in closer after he had slowly lied down on the bed. We kissed some more, gently and softly. To my surprise and relief I could feel myself get aroused. Although I would probably have not given him much attention if I had met him elsewhere, I did think he was a kind and nice guy and I cared for him. Finally I could feel his hand around my waist, caressing and feeling me. "Lesson one. when kissing and all, you can move your hand anywhere, touch and feel anything, as long as you do it slowly and sort of..in such a way that she'll know where you'll be moving it next if that makes sense. Just give her some time to grab your hand to stop you if it's going too fast, okay?"

He nodded and almost immediately showed he had understood the message. His hand slowly moved up, feeling my waist until it came to rest on my left breast. He stopped for a moment and looked at me, as if to ask for permission. I grabbed his hand and cupped it around my breast while I whispered in his ear "Lesson two..top first, bottom after..unbutton my shirt..". Sitting up straight he started to unbutton my shirt while I pulled his off. He wore a plain white t-shirt underneath his shirt, which I quickly pulled off too followed by my spaghetti-top. He stared at my bra, in a way which once more showed how he'd never seen a bra being worn by a woman before, other than online. We lied down again, kissing more passionate now. His leg pushed against me and I could feel his erection pushing against my leg as he finally become a bit more daring, his hand moving down to my knee and up underneath my skirt. He started moving up my legs, teasing and caressing them, finally reaching my panties. I could feel clearly now how wet and aroused I had gotten. I grabbed his cock through the pants he was still wearing, he was hard, really hard and I could see him flinch and gasp. If I wasn't careful I'd risk him cumming right there in his underwear. Gently pushing him away he sat up straight again, still rubbing my leg underneath my skirt. "Take it off", I commanded as I lied back down. He complied, unzipping my skirt at the side and pulling it off revealing my panties. "Lesson three", I said, "if her panties match her bra..she very much planned for things to happen". Nodding to the bathroom I said "Check on the water will you?" I sat down on the edge of the bed, and as he walked back from the bathroom I held out my hands. He moved closer, in between them so I could unzip his jeans and pull them down. "Sssshhhhh..." I let out as he instinctively reached to pull up his underwear. "Don't..I felt it..show me your hard cock please?". He let go so I could pull down his underwear as well, his cock bouncing up as I did so. His cock was fairly normal in size, some 13 or 14cm or so, very firm and curving slightly upwards. "This is the most important lesson I think. Never feel inadequate. What you see online, those sizes, that isn't reality. Your cock is perfectly fine, never think otherwise.". I padded the bed again. "Lie down here?" He listened, crawled on the bed and lied down as I had said. As he looked at me, lying down naked, his legs spread open and his hard cock pointing up, I undid my bra and tossed it aside. He stared again, following my breasts with his eyes. As I lied down next to him I traced my nails over his naked body. He flinched again, as several more drops of precum came out. He tried to remain still, breathing heavily, and it was clear to me he could orgasm at any moment.

"You need to cum don't you, I can tell". He looked back at me.

"Yes...I..sorry..I wanted to last longer but.."

"Ssshh. it's okay. That'll come with some time and experience. It's not late, we've got plenty of time. I'm sure a healthy guy like you will be able to go again in a little while."

He seemed relieved, every once in a while closing his eyes as I slowly teased him, tracing my fingers over his body, cupping his balls and holding his cock in my hand. "Besides, lesson five is it's okay to cum, sometimes it happens a bit sooner than you hoped for but that's fine. It's what you do after that is more important. So focus on her after if it happens, and it'll be fine, okay?". He nodded as I whispered in his ear, now firmly grabbing his cock and slowly stroking it up and down, "I'll let you focus on me later....". We kissed again, his hand stroking my back. I paused for a moment, and looked him straight in the eye. "It's okay..you may cum for me" I whispered as I started to firmly jack him off, going faster now. His eyes opened wide and his back arched up as he started gasping for air. Our eyes met again, I smiled as I pressed on, going even faster now until he let go, his body convulsing and shaking as he came with a deep moan, shooting an impressive amount of sperm over his belly and chest, with more dripping down over my hand which was now slowly massaging his cock. To be continued..