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Wednesday, 11 December 2013

Sex Date With a Hot Pure Top | ❷

[ Previously on... Sex Date With a Hot Pure Top | ❶ ]

This time, he kissed me while in the intimate Folded Deck Chair position and murmured: "Relax. Relax... Forget all distractions. Look at me, look into my eyes. Yeah that's i- Hey hey no! Don't look anywhere else. Just look at me all right? Don't take your eyes off."

[ Reminder: Sexual Content Ahead ]

I maintained the deep erotic eye-contact as he pinned me down and ground into me. I was equally turned on by his impressive skills, and off by the excruciating pain. "Are you completely in?", I asked in the midst of the pain. He chuckled lightly and said no. I clenched my teeth and tried to ride it out.

Then came a point where the uncomfortable pain sent a rush of dizziness straight to my head, followed by cold sweat. My vision was overtaken by white fizzy particles. It was a reaction from my body, telling me that I was actually going to pass out from the paralysing pain. I stopped all activity and took a moment for it to subside.
What the fuck was that?

He came down to my face again with a smile in the same position, maintaining eye-contact as he murmured: "You've never been fucked by anyone before?" I could smell his masculine breath and it was intoxicating. Remembering that I once attempted car sex, I said yes I have.

"Tell me why did you come here tonight?", he kept his smile and dilated pupils on me. It felt like he was reading me. I said: "To have some fun with you of course! But maybe perhaps the other guy's penile size just couldn't compare to yours?"

"You mean I'm bigger?", a huge playful grin showed up on his face. "Yeah, you're bigger.", I replied with a smile. "You gotta relax. You're not relaxed! You're so stiff that I can feel it right here", he patted twice on my groin.

"Relax as in how? Because to me it means not putting any strength, tension or energy into any part of the body. Letting yourself loose like you're sleeping on a cloud. Isn't that relaxed enough? Because I'm doing that.

"You just need to relax. You're not relaxed enough..."

Me: [ In My Head ]
 Jee, what the fuck do they mean by 'relax'? I AM relaxing... until they penetrate and the pain shoots straight up. But how does one relax when in pain? It doesn't make sense. I don't understand.

Then he looked down on my abdomen and mumbled: "I think you're about to come." As my thoughts came back to the present, it was then that I discovered the light trail of pre-cum below my belly button. I argued that it couldn't have been mine because I wasn't hard enough. 

"Not yours? I'm covered in a condom. If it's not yours then who's is it?", he chuckled. He took a swipe at it with his right thumb and pushed it into my mouth. I tasted the salty flavour and shot him an 'okay-you-were-right' look. I persuaded him to let me try again. He was hesitant, but went along anyway.

He decided to put us in the Asian Cowboy position, that way I can ease myself onto him and the pressure will be less on the receiving bottom. However, the pain persisted after a few thrusts so I gave up and he gave up. We stayed in the half penetrated position, panting and awkwardly looking at each other.

"I'm sorry you're not relaxed enough." 

Me: [disappointed]
"Do you wanna just come?"

He: [chuckling]
"Even if I were to come now, I wouldn't enjoy it any more because I know that you're not getting pleasure out of it. And I'm somebody who doesn't like one-way sex." 

"I've fucked a lot of guys and each time, both the top and the bottom enjoys themselves. We'd fuck till we're both drenched in sweat. When I come, I'll come a river and I can reach maximum orgasm. The bottom and I will be crying out in pleasure."

Me: [silent]

"I have to be honest, I don't know if we'll ever have a 'next time' or if you'll come back to look for me, but my advice to you is that you have to relax when you're getting fucked."

The truth of his words swept me away like a tsunami. For years I've fantasised about crazy good sex, and have found myself to be a very 'sexual being'. Now I'm being confronted with a situation where I have to admit that I suck. 
No no no this can't be happening!

His words ignited a fire of determination in me where I just refused to give up. I said let's try again and he looked at me with an exhausted look filled with confusion. I could see it in his eyes that he didn't quite comprehend why a guy like me who isn't enjoying the role, is still forcing himself to go through with it.

We spent the next 20 minutes or so trying different positions such as Doggy Style and variations of the Missionary position. The hottest part was when he made us both stand in the Bodyguard position in front of the mirror as he entered me from the back. He told me to moan as loud as I can because he gets off on it. Oh God! I feel like I'm being ripped apart! It's so uncomfortable that I just want it to end! 

Even though he wasn't completely in, I moaned out loud not in pleasure but in pain. It was horrible and after a while we had to stop again. Somehow, we landed back on his bed, conveniently in a previous missionary position where he was thrusting into me. I kept lifting my head off the pillow to see if he's in.

Then he jokingly said: "What's wrong? Why are you lifting your head? Are you worried that I'll enter you without protection?" That certainly didn't cross my mind so I wasn't so affected by it.

Then it happened! I don't know how it did but suddenly, he pulled out his condom and pushed his bare tip into me. I was just so shocked that my mind went blank and I didn't find the strength to stop him. What the fuck M! Wake up! Stop him! Stop him now quick! You know this isn't part of the deal!

"Hey, hey! What are you doing? Stop. Stop!", finally I hear my own voice speak. He tried to ignore my words for a couple of seconds before stopping. Then he asked if I wanted him to come already and I said maybe it's a good idea. He started to masturbate as I laid tucked under him.

"Open your mouth", he commanded. I acquiesced and he jerked himself off to climax. He moaned loudly as he sprayed in litres. His cum splattered all over me as I swallowed. He reached for the hand towel and started wiping me clean. When I tried to do it myself, he told me to stop being so anxious and just lay back and relax.

"Okay, it's your turn now. Jerk yourself off", he said. With his strong arms supporting his upper body on top of me, I started to jerk myself off as I parked my head close to his right shoulder. I inhaled his scent, nip his ear and kissed his neck. It was heaven. 

I immersed myself in the intimacy, his manhood and every part of his upper body that seem to shelter me. I felt the warm sensation in my heart of actually being under the care of another man. Not just any man but a hot one. The thoughts were strong enough to push me off the edge and I came satisfyingly, revelling in his body being close to me like it will never happen again.

After wiping myself clean, I lay there in contemplation as he walked around to prepare some things to get cleaned up. I visually caressed every inch of the man that was in sight.  How come I never noticed that his ass was equally as fine as his body? I wish I didn't have to worry about pleasing him. Do you think he'd mind if I told him to just lie down and let me play with every inch of his body like a statue?

Soon enough it was my turn to get cleaned up. While in his bathroom, I started to analyse my incompetence. You're not good at sex. You can't take a dick. You can't be fucked. Your penile head is too sensitive. You can't top nor bottom. What's next? What are you going to do now gay loser?

Now we were both dressed and standing in the living room. It is only then that it started to dawn on me how hard and painfully awkward it was to try and make conversation with someone like him, which has never happened to me before.

As he stood at the door not knowing what to do as a goodbye gesture, I gave him a firm hug and a kiss on the cheek as a thank you. I couldn't gauge if he was open to giving us another chance but thanked him anyway for being so avuncular to me that night.

On the long drive home, I thought about the unsafe moment that happened between us and started to get anxious. Okay stop. Snap out of it and stop scaring yourself. Whatever happened, happened. There's nothing you can do about it now except shut up and go get tested.

After drowning the worry out of my head, I wondered if I should see him again. Logic was telling me that I shouldn't get together again with a guy who removes the condom in the middle of sex, but the arousing image of him was still burning in my head.

The next day I sent him a text and there was a positive reply which seem to suggest that things are good between us. I don't know when or if I'll have the courage to visit him again yet, but this sex date was certainly an eye-opening learning experience. I'm keeping my fingers crossed that the next one will either be it or better.


  1. having sex with a superbly hot guy is a rare chance in a way you wouldn't even mind having unprotected sex with him. It's good to know you were able to stop him before he enters you fully.

    Maybe you should try to apply MORE lubricant and being fingered before you being entered. It works for me everytime I encounter someone with large penis.
    Speaking of relaxing while being entered, you should try to not think about the pain causing you. Try grabbing his arms or playing his pec, abs nipples or kiss him for distraction. If you still can feel the pain, tell him to go slowly .. half the slow until your ass can fully take it.

    Don't worry about it man. You are not a gay loser at all. You are just not used to having being penetrated. It takes time to be a good bottom as much as being a good top. Generally, being a bottom has to know the pleasure of being entered. Once you get the idea of having pleasure of being bottom, needless to say the whole sex process would be very much enjoyable - he'd be very happy with you and you would get a second chance. Explore more to find out what develops your pleasure of being bottom.

    some advice from an experienced bottom here. Good luck, mate!

    1. Thank you so much for the advice! I'm sure other guys who are reading this for the first time will find it useful too.

    2. I think I agree with Olivera there. Well, for one thing, you're not a gay loser at all. I get it though. I mean, the definition of gay pretty much leads a person to believe that it's all about sex. But fuck all that and be who you are. And in that respect, stop trying to do what you're supposed to do in sex and do what feels good and the rest will come. I mean, you're jumping ahead a little and thinking about the symbolic nature of fucking instead of concentrating on the actual fucking. Like the whole bodyguard position? I totally get it. Two bodies touching all over and a hard throbbing cock lining up just right. And if you luxuriated on just what felt good instead of trying to get part a into slot b, then it might have been a little better. Be a little selfish. You deserve it. Maximize what feels good and concentrate on that. Ditch the rest. Now for the practical side of things. In "relaxing", sometimes a guy can get pretty tense without knowing it. And there does seem to be two parts of the rectum, one a little more immune to voluntary impulses. But, ironically enough, in my bottom days, when I felt myself tightening up, I actually tried to push the guy's cock out and that opened up my ass enough for him to push in. Hm... I'm trying to be nice and not so crass, but basically what I'm saying is if you act as if you're going to take a dump, your sphincter naturally dilates. Kinda graphic in a not so nice way, huh? Sorry!

    3. Hey don't be Bruce! Graphic explanations usually gets the idea across much better. Thank you! Think I might try your advice too the next time around. lol.

  2. I think if you knew him more than 2 minutes, and became comfortable with him, this would have been far easier. Find someone where you like him and he likes you.....and then take it as slow as you need to.

    1. I understand what you're saying. Hopefully it comes soon enough. Thanks man.

  3. I remembered my first time with a very hot guy. I was so excited and nervous at finally finding a guy that looked like a porn star, I was besides myself. I was also very inexperience at the time too. I was so excited that I shot my load just my kissing him. I still had my jeans on when I did, I just played it off as precum and just worked on him until I was able to get it back up. So you are not a loser, you are just experiencing new things. Now, you can better prepare for the next time. Trust me, there is always a next time.

    1. Thanks for the story my friend and the words of encouragement.

  4. This has brought back a very recent sexcapde where the sex turned out to be so incredible, I felt like he was really teaching me something amazing

    1. Incredible sex while learning something? Nice!

  5. I sympathize with your situation. I'm not new to sex, but there have been a lot of times I've been with men where awkwardness has predominated. Echoing what RB said, I think it probably makes all the difference being with someone who you actually like and being with someone to whom you're physically attracted. I've been in many situations where I'm confronted by a really hot guy, but I just can't get hard or cum just because I am thinking about pleasing him so much. From my experience, this never really works out well. Sure, the other guy may have no problem getting off, but you will be the one who feels incompetent.

    Give yourself time to discover what you like and what feels good with someone who is willing to teach you. Nothing's worse than being intimate with someone and realizing half-way through that what he wants has no correlation with what you want.

    The other issue is barebacking. While I support safe sex practices, if bareback sex is possible, there needs to be consent by both parties, preferably before you have sex. If it is absolutely off-limits for you, you need to clearly tell him before you meet him so there are no ambiguities when have sex. You will feel better for this.

    1. It's always nice to read somebody else's experience and thoughts on this subject. Makes all of us feel less alone. Thank you!