Brother and Sister Learn Together

I replied, "That thought had not occurred to me, but I'll bet you're right. Thanks for sharing those additional insights."

I went into the App and filled out my evaluation online. Was he on time? Yes. Did you feel safe? Yes. Did he respect your boundaries? Yes. How would you rate the overall encounter on a 1-10 scale. 10. Describe one thing you liked most about the person in this meetup. Everything.

Three days went by before I received my next text. I showed up at the appointed place and time but after waiting 10 minutes past the appointment time I left. That hadn't happened to me before, but assumed there was some mix up. A couple hours later I got another text indicating there had been a scheduling issue and apologizing for the inconvenience. I was a little frustrated, but it was understandable that things like this might happen.

That evening, I told my roommate Sarah about my disappointment. She said that had never happened to her, but heard it happened to others on rare occasion.

The next day, I again got a flash text. This one had no issues. The guy arrived right on time and it was an exciting meetup. I got to feel my second cock, and while this one wasn't quite as extreme as my previous meetup, I enjoyed having him explore my breasts. I could really tell my body turned him on.

It was Friday night again and I was looking forward to getting together with my brother and comparing "notes" on our adventures this past week.

"So how did your week go," I asked him with maybe a little too much enthusiasm.

"Oh, just the usual," he replied with a big grin.

"Well, I had 2 meetups during the week. They were both quite exciting. I touch my first penis, so now I can scratch that one off my to-do list. Both guys were quite handsome."

"I actually had 3 meetups. It was quite enlightening. Big surprise, I found I really like both seeing and touching a girl's breasts. I also realized I had no idea what I was doing when it comes to their pussy."

I was quite amazed, here we were, brother and sister talking to each other about a subject as intimate as this, when prior to signing up for the Flash App, anything regarding sex would have only come up in vague generalities, and even then, only rarely. On the other hand, I still wasn't comfortable sharing everything, like how the first guy to give me an orgasm lived 3 doors down from Craig's dorm room.

My brother went on, "Fortunately, the girls I met up with were quite patient. The first gal knew it was my first time 'touching', and after some fumbling around on my part, gave me a little 'tour' of that area. I told the second one straight out to let me know what she liked, so by the time I had my third meetup, that gal told me I was 'great', for a beginner. Another thing that has surprised me is how verbal some of the girls are."

"You mean like when you are playing with their tits"?

"Well yes, there's that sometimes, but I mean comments directed at me. I think of myself as a pretty 'average' guy but these girls go on about my chest, my ass, my blue eyes, and most especially my cock. I know I'm not some hung super jock, so I am not sure why I rate these effusive compliments."

I didn't say so out loud, but their comments about my brother's physical attributes had me curious too. "Maybe it's because they suspected you're a virgin, and that turns them on", I offered.

Not to be out done by my brother, "I think I could say the same about the guys. I get comments that would make you think they've never seen naked boobs before, and you know my breasts aren't huge. Not that I am complaining. Who doesn't want to feel that others see them as sexy?"

I continued, "So, on another important matter, do you prefer shaved, no hair, Brazilian..."?

That elicited a chuckle from Craig. "If you had asked me a month ago, shaved would be my answer, but now that I have seen and felt it up close, I would have to go with neatly trimmed."

"My turn to ask a question," Craig said, "Cut or not cut?"

"Well, only one guy I saw was uncut, so I think I'll have to have a bigger sampling before I can definitely say I have a preference. So, I have a guy question for you. My roommate Sarah, said that if one were to give a guy a hand job to completion, you would need to use some lubrication. Is that true"?

"I still can't believe we are talking about stuff like this. I can only speak for myself, but yes, it makes all the difference. In these meetups where the girl is just giving a guy a few strokes to check him out, it doesn't matter, but for something longer I would definitely suggest lube. Just curious, are you planning on needing some in the near future?"

"Oh, just trying to be well informed," I retorted.

The banter went on for a while longer, but then it was time for me to get back to my dorm and get to bed.

As I lay in bed trying to doze off, I found that more intimate conversations with my brother were causing me to be a little bit conflicted. While my twin had always been my best friend, confidant, and cohort, I was beginning to also seeing him as a "man". A man with sexual needs and desires. Until recently, I had never really stepped back and looked at him as a male. I realized that a lot of traits I found attractive in a guy, were traits he had as well. I also started to wonder if he ever thought of me as a "woman". Did he find me attractive? Did he ever check out my ass or breasts when I wasn't looking? I found myself a little jealous of the girls that had meetups with him. He got naked for them, total strangers, yet me, his best friend, had no idea what the intimate parts of his body looked or felt like.

Another two days went by before I got my next Flash text. I had gotten just a bit obsessed with touching a guys cock the past few days, and had even searched for some online porn showing girls giving hand jobs. There was a lot to choose from. I didn't know if the opportunity would arise, but I actually procured a small 'sample' size bottle of massage oil and stuck it in my pocket and then headed off for my meetup.

I got to the appointed room and entered. It always amazed me how the app knew which room to send you to and that it always seemed to be available. Then a young man entered. This was something new, he appeared to be 'sort' of oriental looking but not quite. Like so many Americans, I thought he was probably mixed race. He had black hair and dark eyes and looked to be a few inches taller than me. He greeted me with a big smile, a nice greeting and then said the security code I was waiting for.

We faced off for a few moments, standing about three feet from each other. He then reached to pull his shirt off. He had a nice chest, with just a hint of chest hair. He looked like he must do some sports, because his chest muscles showed some nice definition.

He reached for his pants next, but I stopped him. "Can I help you with those," I almost pleaded.

"That would be nice."

I actually got on my knees, which put my eyes just about level with his crotch. Putting my internet training to good use, I started by just running my hands over the front of his jeans. I soon located the "lump", that I was sure must be his cock. I took my time and ran my palm and fingers over it and could feel it quickly getting larger. Next, I unfastened the top button, and then slowly unzipped the fly. His pants dropped to the floor. His tented briefs were next and I tugged them down and over his swollen member. His cock was right at my eye level. I reached out and touched it with my fingertips. I looked up at him and smiled. "You have a beautiful cock". I continued to gently fondle him and soon he was at full attention.

I stood up, as now it was my turn. I peeled off my shit and then unfastened my bra. Putting my "fabulous" breast, at least according to verbal testimonies I had from four different guys, on display. Then I removed my pants and finally my panties, revealing all of me to him.

"Oh my, you're gorgeous." He said as he took a step closer. "May I touch you please?"

I nodded my approval. He reached out and touched my cheeks first and then his fingers slowly trailed down my neck and then over the tops my breast and finally my taught nipples. It sent a shudder through me. Next, he moved around to the back of me and wrapped his arms around me and cupping both breasts in his hands. I felt him gently pulling me back until my back touched his chest. He massaged my breast for a short while and then his hands began to slowly trail lower until they were over my sex. His fingers played through my pubes and I felt his erection gently pressed against my ass. His fingers went down lower as he gently parted my lips and ran a finger over my slit, making me jump slightly. He paused there and I just enjoyed the sensation of our closeness for a few moments.

I broke away from him and remarked, "That was wonderful."

It was hard for me to interrupt our moment but, I had come with my own agenda. I asked him, "I am really new to this, and I've never seen a guy cum. I know it may take more time than we should use, but would you allow me to give you a hand job?" I thought to myself - this guy probably thinks I'm nuts.

He broke out in a big grin and said, "I don't think I refuse a request like that,"

With that 'green light' I dug the little bottle of lube out of my pants pocket. I held it up for him to see. "My friends said I should use some lube."

He smiled down at me, "You really came prepared."

I got down on my knees again, opened the bottle top and poured some of the oil over the top of his stiff erection. It twitched little as the liquid poured down its length. "Now, if I'm doing anything wrong, be sure to let me know." With that, I wrapped my hands around "it" and started administering my first hand job.

The oil really allowed my hands to glide over his erection easily. I went up and down its entire length a number of times. I then moved one of my hands down to his ball sack and massaged it with my oily fingers.

"That feels really good," he said encouragingly. Being on my knees, his cock was just inches from my face. I watched his manhood slide through my hands. He was very hard except for the softer more pliable tip which I polished it too. I gazed up at him and he had a look of real enjoyment on his face. Momentarily, I moved my hands farther afield, running them up to his taught chest and then up to his nipples. I ran my fingers thought his pubes, between his legs and squeezed his upper thighs. Then I put his hands, which had been at his side, in mine and reach for his erection again. I placed his hand on his own cock and said, "Show me how you do it."

He seamlessly took over from me, wrapping his right hand firmly around his own cock, which was still slick from the massage oil. I was mesmerized watching the "expert" pleasure himself. I could see that he concentrated on the upper third of his prick and then occasionally stroked its entire length. His hips started thrusting too. I placed one of my hands over his and we worked together. "You feel so hard and strong, I want to see you cum for me." I encouraged him. I brought my other hand back into the action and took over pleasuring him. I didn't need to move my hands much as he was thrusting hard, forcing his own cock in and out of my enclosed hands. I could hear sounds of pleasure coming from him that told me he was getting close. "That's it, I can feel you're almost there".

The force and speed of his thrusts increased as I tried to keep my hand and fingers wrapped around him. Then, bam! a stream of cum came squirting out of his cock and hit me in the upper chest. Two more ropes of cum followed in quick succession landing on my breasts. It was warm and thick. I released his cock from my grip. Because of the videos, I was also prepared for this. I retrieve a wash cloth I also brought with me.

First, I gently wiped some cum left on his now shrinking member. He said, "It's hard to believe that was your first-hand job. I really enjoyed that." He then took the wash cloth from me and tenderly wiped my chest and breasts off.

We both reluctantly got dressed and headed our separate ways. I guess I was rather pleased with myself, at least for a while.

I was coming to realize that while each of these meetups was exciting, the "high" was rather temporary. Sort of like eating a candy bar. Once it was done, there was not much lasting satisfaction. I suppose on the plus side, I was feeling more confident about myself, my body, and was more comfortable and even looking forward to interacting with the opposite sex.

I told Sarah about my successful hand job at dinner time.

It was four days before I got my next Flash text. I had actually been less obsessed with the App since my last meetup, so had not been waiting with quite the same urgency for a text as I had the previous few weeks. But, now that I had gotten one, I could feel my heart beat a little faster anticipating my next encounter.

I grabbed my supplies, the remaining massage oil and a wash cloth, just to be prepared. I then headed over to the music building and the practice room the App indicated.

I got over there just a minute before I was due and slipped into the empty practice room that I was to meet my next partner. I waited for a number of minutes, and was beginning to wonder if they were going to be a no-show. Then the handle turned and he stepped into the room. I could feel my heart started pounding. It was my twin brother Craig. He recognized me at the same time, as he stopped in his tracks, just 3 feet in front of me. We just stared at each other for what seemed a long time. As we did, I looked at my brother, like he was man I was seeing for the first time. I saw a handsome, clean shaven, slim, even sexy young man with sparkling blue eyes, but because he was my brother, I also knew that he was kind, caring, smart, funny and more. At that moment I felt like he was exactly who I needed to come through that door. I had no idea what thoughts were running though his head, but it was probably 'how do I get out of here.'

When it looked like he was going to turn and leave, I called out, "Craig, wait, I want to tell you something."

He turned back toward me.

"I know these past few weeks have been quite a whirlwind for both us. I know I've learned more and done more with guys in the past few weeks then I would have ever imagined a month ago and I know it's been the same for you. I've really enjoyed confiding my adventures with you and you confiding with me. While I have totally enjoyed these meetups, they aren't wholly satisfying, because I don't even know these guys and they don't know me. I want to do this with you, someone I love and care for. I think maybe fate chose us to both be here for this meetup. I totally understand if what I just said freaks you out, and you can just go out that door and we'll pretend this conversation never happened."

My brother stood frozen for just a few moments and then took the two steps, closing the gap between us, and wrapped his arms around me in a full embrace. He was almost in tears as he whispered in my ear, "I love you so much." I hugged him back and shed some tears of relief and joy myself.

After while we stepped back from our embrace.

I tried to lighten the mood, "Hey, what's the security code?"

He laughed and said he'd forgotten it.

We both knew from our past experiences what was expected next. I stood patiently, waiting for my brother to start taking his clothes off for me. He didn't disappoint me for long.

He grabbed his shirt and pulled it over his head. As I already knew, he had little to no chest hair. I did appreciate his flat stomach with just a hint of a six pack. Next, he unfastened his jeans and they dropped to the floor. Last to go were his briefs. His hands were shaking as he lowered them down joining the jeans on the floor. He wasn't hard. I thought probably seeing his sister when he opened the door took care of that. He had a nice package, with neatly trimmed blond pubes, and his cut cock hanging over his sac.

"Turn around, I want to see that cute ass of yours"

He did so, and it was indeed a pleasure to look at.

"Ok, your turn," he said to me.

I was not even two feet in front of him, as I pulled my shirt off. Though I knew I could do it myself, I turned my back to him and said, "Please undo me." He reached over and his inexperienced fingers eventually met with success. My bra fell to the floor and I turn back around presenting my naked breasts to him for the first time. I look down and could see that penis approved of what he saw. He wasn't hard yet but he was getting there.

Looking at my chest Craig exclaimed, "They look more beautiful than I ever imaged."

Now I dropped my jeans and then finally panties were removed. We both stood there naked each studying and admiring the other. My brother was fully hard now, with his proud erection pointing to the ceiling. I am sure he has checking out my pussy. I stepped forward and kissed him and once more we embraced, though this time I could feel his hard cock trapped between us as my breasts pressed against his chest.

We separated and he asked, "May I touch you"?

"Yes, please touch me everywhere."

He took one of his hands and cupped my breasts. It felt so good to have him touch me. He teased my nipples causing me to whimper. I reached down and wrapped a hand around his hard member. His size and hardness felt impressive, though it was likely not the largest I had seen over the past few weeks. It had beautiful proportions and was very straight and capped with a nice mushroom shaped head. I heard him moan as I ran my hand over the length of it. His hands trailed lower and I liked where he was headed. Soon his hand was cupped over my wet pussy and I spread my legs to give him better access. He ran his finger over my pussy lips and down my slit. I could feel his finger probing and then felt one go inside me. I let out a small gasp.

He continued to explore me, sometimes fumbling but other times hitting just the right spot. He was definitely sensitive to my verbal cues as his hit rate was definitely improving. I felt fuller, as I think he now had two fingers that he was pressing deeper inside me and hitting my spot. With his other hand he was fondling my tits and sometimes pinching at a stiff nipple. Then he was regularly brushing over my swollen clit giving me almost overwhelming pleasure. I am afraid my efforts please his cock was nearly abandoned, as I was being overwhelmed by the pleasure Craig was giving me. I heard myself begging him not to stop, as the intensity increased. That seemed to make him press even deeper and firmer. The orgasm hit me hard, and I tried to stifle the screams of pleasure I wanted to make. He would have to be satisfied hearing me whimper like a winning puppy. He continued for some seconds until I couldn't take any more. He stopped and allowed me time to recover my senses and just held me.

"Wow, I think your practicing is really paying off, that was fantastic." I said.

"Well, that's the first time I have every given a woman an orgasm."

"Then I am honored to have been the first," I said with a smile.

"Now I want to take care of this," I said as I wrapped my hand around his cock.

I paused a minute and fished my massage oil bottle out of my jeans pocket.

I then stood behind by brother and then reached around him and ran my hands all over his chest. As we were in a music practice room, there happened to be a large mirror on the wall opposite us. Craig could look in the mirror and see my hands feeling him up. I moved my hands down and I cupped his balls and massaged his pubes. We could both see his cock bouncing around from my motions, but always returning to its upright state. I took the massage oil and poured it into my hand. Then I reach around again with both hands and spread the oil over his entire cock. We both looked at the mirror, and watched my hands slide up and down his pole over and over again. I changed up a couple times, using one hand on just the mushroom tip and the other to tease his sac.