Both Sides of The Field

by Ben

20 May 2023 2291 readers Score 9.7 (49 votes) PDF Mobi ePub Txt


Whether or not this is a good idea rushes through my head but this moment is something that I never thought would ever happen. Henry’s hands run along my abs and up my chest as I watch him with so much eagerness just wanting to feel my pecs which are solid but not as big as his but I see him smiling getting to feel my body right now.

I lean back so my abs flex as Henry starts to kiss them going up my body, as I moan and feel his surprisingly soft lips kissing my pecs right now as his hands also run around my chest still. As he continues to rub and kiss my body, I lean over and take off his shirt and gasp at the size of his muscles and how firm they are for their sizes.

Despite always wanting to be the centre of attention, Henry pushes me away from touching him as right now he just wants to focus on my body right now as I close my eyes and moan, knowing that I’m getting harder in my shorts and trying to not freak him out.

Going up my body, Henry kisses my neck and I can sense that he wants to kiss me and I want to kiss him as well but every time we get close to kissing properly he pulls away. “We don’t need to do this, I never was expecting this or anything” I say to Henry who nods at me before just pausing as he was about to say something.

“But I want to do this with you Jacob” he says I actually see a boy that wants to have a romantic experience right now but doesn’t know how to do it at all and that for someone so confident even in the biggest Rugby games, the nervousness of this is taking control of him as he is slightly shaking.

Hearing him say that he wants to do this with me stuns me into total silence and shock as I didn’t expect him to say that at all and just take in this moment. The pause of me in shock catches Henry by surprise “Did I say something wrong? I fucking knew this was dumb to think that you were genuine” he says as I grab his arm as he gets up.

“Hey, I want this too but I just never expected you of all people to say something like that to a guy like me”. Henry turns around, still with his shirt flung onto the floor as I stand up and look at him “I’ve never had a moment like this ever and this is all so new to me” my raw honesty probably not the best look but for all the dreams I’ve had of being with a guy and in my first romantic moment and it being so easy there, it’s terrifying doing it in person let alone with Henry Walker.

“I know you’ve been with girls and dated them so you’ve had all the experience in the world of what it’s like to have sex for the first time and kissing a girl and just all that stuff” I say as Henry turns around again and his deep voice goes extremely shy and quiet as he mutters something under his breath. “What did you say? Go ahead, take the crack that you know you want to that I’m probably the only guy at this school who’s not going to be a priest that is still a virgin because I know all about the tally you guys keep”.

Henry just turns and looks at me annoyed by what I just said “I’m a fucking virgin alright” he says angrily almost as if he thinks that it’s a bad thing and that I’m trying to do it to rub the fact in.

My surprise is through the roof as I hear him say that because for all the bullshitting about who he has been with, I thought it was just him embellishing the truth, not actually just making it up completely hiding both the fact he’s gay and still a virgin.

I stand there for a minute and hold his hand as he is so unsure right now “I didn’t mean anything by the comment at all ok? I was just saying what I thought I knew” I say as I don’t know how Henry is going to react as he just sits on the couch again.

“You’re the only person in the world that knows about my secret and first person I’ve felt that I could do this with” he says as I put my arm around him to show him some love because I’ve always sensed from our first conversation there isn’t a lot of love or support in his family.

I sit there rubbing his shoulder telling him everything is ok “It’s ok to be in this situation, it makes us who we are and right now the most important person is you and what you think should be the only thing that matters”. I don’t know whether my words help but Henry just looks at me and puts his head on my shoulder as I keep rubbing his back.

“Thanks Jakey” he says to me as I smile and try not to push him too fast and push him out of his comfort zone as we just sit there and enjoy each others company. I don’t know how long we sit there before Henry looks at me and holds my cheek stroking it for a moment before he nervously comes in and I feel his soft lips against mine as our first kiss is quick as he looks at me as we both smile.

There’s a cheeky grin on both our faces right now as we just nod and go back into kissing each other this time the nerves seem to be gone as our arms wrap over each other and we both start making out and for me at least there is something relatively normal about this. Henry for his big and tough exterior is really passionate as we make out and I feel him use his muscles to push me onto the bed as we continue making out.

I lay on the bed as Henry continues to kiss me and I feel his pecs up against mine as we make out and again he quickly kisses down my body as I run my hand through his hair. The worshipping of my body right now is amazing as I thought for sure that Henry would be so dominant but he just keeps kissing me as I feel his slowly moving my pants as he rubs my bulge in my cheap briefs as I moan.

I keep my eyes closed, partly embarrassed by how cheap my underwear is but just enjoying the moment feeling a stud like Henry Walker now holding my cock in his hand. Henry starts to kiss my cock as I reassure him about only doing what he’s comfortable with which seems to be a lot as he sucks on my head before going down further. Letting Henry get used to sucking cock, is actually amazing seeing this guy who is simply a narcissist not caring about anyone else, now solely focused on how I feel.

The blowjob is amazing as Henry goes deeper as he tries to get used to having 8 inches of meat down his throat. His efforts are amazing as my leaking cock are adding difficulties for him right now but as each bit of pre goes down his throat it gets easier as my first blow job feels expertly done even with the moments where Henry has to stop to regain his composure and just take a break.

I look at Henry as he takes a few deep breaths “You’re doing amazingly but remember” before I finish my sentence, his head is back over my cock and sucking it deeper than he did before still trying to get used to the taste of everything as I moan loudly. I look at him as he slides himself out of his pants and briefs in one swift move and I see his meaty cock as spring out.

Henry isn’t what you’d call hung but there is a pretty solid girth to his cock and I’m even more surprised that whilst trimmed he still has a fair bit of hair around his pubes. “Holy shit” I say as he smiles at me and rubs my chest before going down deeper on my cock and feel his nose hitting my skin as my whole cock disappears into his mouth and deep down his throat.

My cock leaking as I’m trying to control blowing my load too quickly right now as Henry can sense my cum flowing and pulls off almost repulsed at first by the thought but then after a few deep breaths he goes back down on my cock sucking on it and his head going faster.

Henry feels me about to cum and quickly pulls off trying to make sure that I don’t “Want me to suck you now?” I ask him as he nods and he lays down on the bed and gets into position for me to go down between his muscular thighs.

My confidence is shot right now because I thought that I could do this easily but the panic is running through that I’m going to be so turned on by him sucking my cock but the job that I do is going to be just awful. I slowly put my mouth over the head, trying to replicate what I’ve seen in porn trying to make Henry enjoy it.

I slowly go down further and Henry moans enjoying the feeling of my mouth sucking on his hard cock right now as I can feel his full balls right as my hand goes down to massage them which turns him on more. Henry slowly grabs my head but instead of holding my head, he is just running his hand through my hair enjoying the feeling and taking in the whole experience.

As our cocks leak, Henry climbs to the other end of the bed and we start sucking on each other right now, both of us moaning loudly now and thankfully the walls are extra thick because right now we’re both getting pretty loud. I pull off his cock and look at him “So are we going to fuck?” I say not sure whether Henry wants to do it or not right now.

Without saying he gets on all fours right now and just looks at me waiting for me to fuck him as his ass is also surprisingly hairy as I push my face deep into his firm beefy ass right now, tonguing his hole as he starts moaning as my tongue goes to work on his hole.

The feeling of his firm ass is amazing and it was weird because in my head even though I wanted to be with a guy, rimming and licking another guys hole seemed to be weird and a bit gross to me but now that Henry has his ass open, I’m so into it and Henry is loving it to.

As I rim his hole, I push my finger in getting him loose and trying to open his extremely tight hole which he grimaces at getting just the single finger in his hole right now. Finger fucking him, I just want to get him ready for a real cock in there because even though I know I haven’t done it yet, I know that the real thing will hurt a lot when I start to fuck.

I look at Henry as I stand there “Want me to fuck you raw or condom?” I ask as he thinks about it for a moment as I can’t tell what he’s thinking right now. “Raw” he says as I smile and he check whether that’s what he wants right now as I start to get more dominant as Henry is begging me for my cock to fill his hole.

Grabbing Henry’s hips, I pull him closer to me as I grab some lube that I keep for when I jerk fantasising over guys like Henry and his friend Toby. Having Henry just submitting to me right now is amazing and he moans begging me “Fuck me Jacob, I want your cock inside my tight virgin hole” he says begging me as I keep teasing him and slapping my cock onto his crack and hole right now.

“Fuck I need that so badly baby” Henry is on the bed begging me to fuck him as I enjoy being the dominant one right now and the most powerful guy both on the rugby field and around the school but right now he has no power and control and has to beg. “You think you can handle my cock” I say slapping Henry’s ass with both my cock and hand right now as he’s nodding and I’ve got him in my hands right now.

Henry moans as I do it “Fuck I need your hard cock pounding my ass so deep, make me moan baby” he says to me as I smile and start to slowly push the head in. “OH FUCK” it’s only the tip going in and I can see Henry gripping the sheets on my bed right now.

I close my eyes as I start to push in further as Henry is trying to control his breathing right now to bear the pain of my thick cock going into his virgin hole. “You ok there?” I say as Henry just moans right now and I smile knowing that this is going well so far.

Keeping my cock in there right now but not pushing further or pulling out just because I want Henry to get used to the size of my hard meat in his ass and I wait. “Fuck that hurts but it’s amazing bro” he says as I start to push in deeper until he groans loudly “FUCKING HELL THAT HURTS LIKE HELL” he says and I know that he has been through a lot of pain on the field.

Without his say so, I start to pick up the speed as I start to fuck his virgin ass as we are here both losing our virginity right now. Henry is moaning as I keep pushing deeper into his tight hole and I’m fucking it hard as he has turned from moaning and groaning in pain to moaning and groaning in pleasure knowing that he is enjoying the feeling of being fucked.

I pull out of Henry and flip him over because I want to see his face as I fuck him and putting his muscled legs on my shoulders is heavy work but I quickly forget about as my cock goes deep inside him and I can see his eyes rolling back into his head in pure pleasure as I keep fucking him deeply.

“Holy shit yeah, fuck my tight ass Jakey” he says as I just take control balls slapping against his ass right now, really hoping that nobody is home next door because my bed is banging against the wall hard right now as I’m balls deep inside one of the school’s most prominent students right now and tough Rugby captain is now just a bitch on my bed.

I’m fucking Henry hard right now as he moans and I can see his cock leaking on his chest right now as I can feel myself wanting to cum. “I’m close to cumming baby” I say to Henry who nods his head “Just don’t cum in me bro… I.. just…” I pull out of his ass right now and start jerking my cock and ru it against his right now before we both blow at the same time all over our bodies as I lean over and kiss him.

Henry grabs my head as he lays there and right now the kiss turns into a full on make out as our sweaty bodies are now on top of each other as I run my fingers over his cum soaked chest and suck on one before getting him to taste our loads mixed together.

Gaining our breath back, I look deeply into Henry’s eyes “How did that feel?” I ask as I can tell in his head that he enjoyed it but there would be so many emotions going through his head having just lost your virginity to someone you hate or at least that’s what I’m thinking he is thinking.

“It was amazing baby” he says as the romantic side to him is really coming out and I think there is some actual affection for me. “I’m glad, I thought maybe that you regretted it with me” I say my confidence probably lacking compared to where it should be.

Henry looks at me as we lay next to me and he kisses me for a moment “No way at all, it felt really special to do it with someone I feel connected with” he says as I smile at him as we lay there both still naked taking in this moment.

“Can’t believe that we just lost our virginity together… I’d never thought I’d have sex with Henry Walker” his smile right now is a touch embarrassed by that comment. “I’m glad that I did it with someone who is special like you are, you are an amazing guy”.