I am a tall, pretty (25F) Chinese girl, nice face and long hair.

I tend to make female friends as I feel more safe around them, but in the past I have also had gay male friends. I find that most gay men are smart, smell good, look good, and are interested in my personality more than my looks. They don’t want sex from me and are interested in just being friends. We also share a lot in common.

Three weeks ago I was in Singapore and I met Jack, a very successful interior designer who has his own company. He’s tall, half Chinese, half American. Brown eyes, short black hair, quite handsome. He comes from the U.S. but has travelled a lot throughout his life. He played basketball when he was younger and now he’s busy running his business and being a socialite. I met him through a friend we have in common. The first time we met, I could immediately tell that he had no interest in me whatsoever. His mannerism and the way he spoke to me made that abundantly clear.

We exchanged numbers and went on a few lunch dates together as friends. I was surprised when he revealed to me that he’s gay. Nothing about his personality suggested that he might be gay, except perhaps his deep understanding of women and human psychology. When we talked I felt that he really cared about my feelings and could understand me so well. We shared more and more intimate details about our lives and spent more and more time together. For about 12 days, up until two days ago, we were inseparable.

Two days ago, the friend we have in common invited us to her birthday party, so Jack and I met there and talked for quite sometime. I was wearing black high heels, a short white skirt and a pink sweater. He had a grey Nike track suit on and some designer shoes. After a couple of hours, all people there with us were drunk and started making a real mess (One girl threw up in the Jacuzzi). There was a lot of noise and the music was loud, so we decided to go inside and find a room.

I don’t remember how the conversation started or how we got to talking about sex, but we did. He was talking about his recent adventures and I was mainly listening and learning. I admitted to him that I had never had anal sex before, even though in the past guys did ask. My asshole is “virgin”. He couldn’t believe it. He went: “Are you crazy?? It feels so good!”. We both bursted out laughing, my face was now red.

He says: “How about this, I can show you right here, right now!” I go “What?! What do you mean?” He explains that he would be very happy to show me how he inserts a small butt plug into his ass. I am embarrassed but also extremely curious and entertained. We both have drunk a little wine and I find the situation funny. Also, I don’t want to make him feel bad, or make him think that I want to distance myself from him in any way due to him being gay. So I say “Ok, go ahead. Show me!”

He leaves the room and goes looking for his coat. Meanwhile I check my phone and text my friend asking how she is doing and if she wants to meet me. After a couple of minutes, Jack comes back with a little transparent plastic bag containing a red butt plug and lube. “I thought you said SMALL” I say. He giggles a bit, then takes the butt plug out and puts it in his mouth. We laugh. He tells me “There is no pain, only pleasure”.

We are both sitting on the same side of the bed and suddenly he stands up, takes the plug off his mouth and asks “Pull my pants down”. I try, but it’s awkward to it from the side, so I stand up and then kneel in front of him to take his pants down. Suddenly there is complete silence in the room and I look at him, he looks at me and smiles. I look at him and smile trying to hide the fact that I am a bit nervous at this point. I pull down his underwear too. He has a pretty small cock. But good hygiene. He’s completely shaved and has clear skin. He picks up on me getting nervous and in an attempt to de-escalate tension, says “Is it because it’s too big or because it’s too big and I am Asian?” That made me laugh. He sits on the bed and says “You know, this works better when I am excited”.

I am hesitant, so he takes my hand and pulls it towards him. Initially I struggle to stroke it as it’s too small, so I massage it a bit. Thankfully It gets hard pretty quick and can I jerk him off. I was actually surprised that someone who is allegedly not attracted to women can get so hard, so quick. That should have tipped me.

After a little bit, he pulls his legs up, holding them with one arm and uses his other hand to use the lube and insert the butt plug. It slides right in. He goes “Now you pull it out!”. He once again takes my hand and pulls it towards him. I grab the plug and I pull it out, gently. As it comes out, he lets out a moan, then he puts his legs down. His eyes are closed and he’s now smiling, accomplished. He stands up, hugs me and says “Congratulations! You’ve just had your first butt plug lesson and I am happy to report that you have passed with flying colours!” We both laugh. “So, would you like to try?”

I am scared but I am also quite horny right now, and I trust Jack, so I don’t think too much about it and say “What if it doesn’t fit?”. “Don’t worry, I’ll be gentle” he says. I bend down to take my high heels off but he stops me immediately and says “No need”. He comes close to me and puts me on the bed, in doggy position. My knees are near the edge of the bed, still wearing my high heels. He puts one hand on my head, pushing down softly. He wants my face and my chest to rest on the bed. When he’s happy with how I am positioned, he quickly lifts up my skirt. That sent shivers through my spine. He quickly pulls my underwear to one side, without removing it and goes “Wow! it’s not very often that I see one of these!”. We both laugh, I like how he breaks the tension and makes me feel comfortable, as if we were kids fooling around. I am still nervous. He says something like: “You’re so small and beautiful down there”.

He leans down to look at me, “Are you comfortable?” I am very nervous but I just go with “Yes”. He then puts some lube on his hands and then softly applies it around my butthole. The lube is a bit cold but his hands are very warm and his touch is soft. I can tell he’s done this before. He puts some lube around my hole and then spreads it evenly, moving his fingers in circle, making the circles smaller and smaller. He finally stops and pushes in slightly with his index finger, exerting pressure on it. It’s very tight. As he pushes in, I suddenly feel very weak, as if all energy left my body.