Reflections on a Painful Past Ch. 03


This wasn't right. I belonged to Claire! Didn't I?

Not good enough, my resolve was withering in the light of my newfound joy. A joy that came from Jack not from my Goddess.

Desperate scrambling in the darkness in the bedside cabinet.

Claire's finger tip vibrator. Yes!

Flat batteries! SHIT, no!

Unsatisfied desire. Searching for something.

Hairbrush. OH! This is naughty!

Sweet satisfaction as the hairbrush handle vanishes into my need. Sweet satisfaction as I ride out waves of pleasure echoing with words in my heart, words that weren't Claire's.

It had been three months since Claire left. She emailed me about once a week, sometimes less. Her emails left me feeling cold. They were full of information but lacking love. I sent her an email telling her what I'd done with the hairbrush. I didn't tell her who I'd been thinking about at the time. She sent me a reply.

>Jesse, you can't email me shit like that while I'm here. Babe these emails aren't private. I love you. Behave yourself. ;)

Well fuck you too!

Jack invited me back to his flat one night when his sister wasn't home. I knew what this invitation really was.


How many times had I said okay to Claire like that? How many times has that simple little affirmation gotten me in deeper than I could cope with?

Jack's flat was nearby. He offered me a beer as I looked round his lounge but I declined. I was nervous at what I was pretty sure was going to happen. I felt a little sick inside at the thought of it. I really wanted this intimate experience with Jack but my fear of what would happen when Claire found out overruled all other feelings. Jack came back from the kitchen with a beer for himself. He looked as nervous as I felt.

That brought a little smile to my face. At least he wasn't scary.

"I'm really nervous Jack." My hands were shaking.

"Yea me too."

That was surprising I hadn't expected him to be nervous. He was a confident man. Maybe he was having second thoughts?

"Jack it's not too late to change your mind. You could be with someone special..."

"Jesse, don't say anything else. I wouldn't want to be with anyone but you. These last few weeks I haven't been able to think about anything but you. Please Jesse I know you're afraid but give me a chance. We don't have to do anything you don't want to. But please stay with me. Stay with me tonight, okay?"


"Thank you!"

His eyes lit up. I could see his excitement. He took my hand and pulled me towards the door to his room. I let him lead me. Inside I was very conflicted. My default mode in times like that was obedience but guilt was preventing me from getting excited.

"Can I kiss you Jesse?"

"Yes please!" He did.

Stubble! That's a new discovery; he'd been clean shaven the last time we kissed. It reminded me of scratchy hugs with my dad.

"Jesse you're as stiff as a plank. Do you want me to stop? I'm sorry. I shouldn't have pushed you. You don't want this do you?"

He hadn't liked it. Shit! Failure! I was failing already. How stupid of me to ever think I could please a man. What man could desire worthless shit like me? We'd hardly started and I was already failing. My darkness rose up and overwhelmed me.

"Sorry Jack. I'm sorry. This was a mistake."

I fled. Alone in my car I cried. I drove back to barracks and cried more.

The next day at work I achieved nothing. That night I stayed home alone until the phone rang. No one had the number not even Jack so I was reluctant to answer but with Claire on deployment I thought I'd better pick up in case it was important news. It was the gate guard station. A civilian had pulled up and asked for permission to visit me in barracks. Visits were allowed but the guard had to verify the person was who they said they were first.

"Who is it?"

"A student from the University, drivers licence says Jack Hesler."

"Yes, I know him. Please let him through."

I'd been sitting in the dark in my dressing gown and slippers. I quickly pulled on a pair of jeans and a t-shirt. The room didn't need to be tidied. One of Claire's rules was that I had to keep things tidy. I obeyed even when she wasn't home. It was only five minutes before there was a knock at the door.

He looked like he was nervous but pretending not to be. I couldn't help but smile as I pulled him inside and looked back down the corridor to ensure no one had seen him arrive. Soldiers love gossip. Strangely I wasn't nervous. At the time I didn't think about it but I've since reflected and come to understand that it was because we were in my domain. This room was my place and I wasn't afraid of Jack. By coming to me here he had done exactly the right thing. Already he was living up to his promise; he was making me feel safe.

"Look Jesse, about last night, I'm really sorry. I was pushing you..."

"No Jack! I'm a mixed up girl, that wasn't your fault. That was me. I want what you're offering so much but I'm afraid... and I feel guilty too. I feel so guilty, for Claire."

I had found my voice, there in my safe room with the door locked and the familiar items of my life around I'd found my voice and the bravery to use it.

"Jack I have fallen in love with you, I promise you that is true no matter how much trouble I have with anything more. Last night I failed you. You wanted a kiss and I couldn't even do that right. I don't know how to please a man. I've never even thought of pleasing a man before. I don't think I'm going to be able to give you what you want. But I'll try. You can punish me when I fail and I'll try harder next time."

He was looking at me with a funny look in his eyes.

"Jesse, I hardly know where to start. You are right you are a mixed up girl but I love you for it. You are so vulnerable that it makes me want to bundle you up in cotton wool and protect you from the world. You are wrong about failing last night though. Love isn't a test. There is no pass or fail. We will explore together and we will learn what works and what doesn't work. We will find what's right for us and if some things don't go so well then that's fine too. I'm not going to be punishing you for anything Jesse. That's just not me."

His words left me confused. Of course it all sounded wonderful and lovely but how would I know what to do? Where were the boundaries? How would I know when I was being good?

"I don't know what to do Jack. What am I supposed to do to please you? I'm not wired like other people. I need discipline. I need you to tell me what to do."

"You need that?"

"Yes. It's just who I am. I can be good but you have to tell me what the rules are."

"Ok sweet heart, I understand now. This is what I'm going to do. I'm going to kiss you again. This time you're not allowed to run away. Afterwards you have to tell me honestly if you liked it or not."

He was a clever a man, I could see where this game was going and I liked it!

"Will I get rewards if I do this well?"

"Yes definitely!"

"And punishments if I don't?"

"No! I've already said no to punishments. There will be no more punishments Jesse. I know you well enough to know that you will try to be good for me. You will won't you."

"Okay Jack." I meant it. I was falling deeply in love with this gentle man and I was going to be good.

He stepped forward and awkwardly I accepted his embrace. We were still breaking the barrier that had existed between us and the new intimacy was not a comfortable fit yet. But when his lips met mine it was pleasant enough to melt any unconscious resistance. It was our third kiss and I was expecting the whiskery prickles this time. I wasn't nervous and I wasn't stiff as his arms wrapped around me. His kiss had none of the powerful intensity of Claire's. He'd never 'own' me with a kiss like this but I liked it. It was a kiss he could 'love' me with.

Claire had a habit of slipping the tongue straight away in a kiss, invading my mouth like a conquered territory. Jack was much more subtle; he kissed each of my lips separately. First sucking on my lower lip a bit and then when my mouth opened in response his tongue licked gently along my top lip just inside my mouth. I felt an instant response as cold fire ran across my skin and found a home between my legs. I couldn't help but moan and he stepped away. He left his hands on my hips though.


I was breathless and excited, definitely aroused but too shy to say so.

"Jack it was a lovely kiss. I liked how gentle you were with your tongue. The only thing that could have made that any better would be if it had gone on longer and if you had gone on to do more."

He didn't say anything; he just pulled me back in for more. My desires were a match for his and I found that in fact I didn't need to be commanded. I didn't need to be dominated. I didn't need to submit. I could actually really, really enjoy just participating. This was a strange new experience this kiss. He was pulling me towards one of the beds and I pulled my face free for a moment.

"That's Claire's bed, I'm not allowed there unless she says. This one."

I pulled him down to my bed. He was pulling at my clothes and I helped him get my T shirt up and over my head. I wasn't wearing a bra underneath and without waiting he pushed me back down and started kissing my breasts.

Intense pleasure!

This was not at all like when Claire kissed them, his stubble was scratchy and I loved the little prickling around my soft areola as he sucked gently on my nipples. The combination of pleasure and light pain had me gasping his name as I ran my hands over his upper back and through his soft brown hair. He was a slight man but compared to Claire he was solid. She was muscular but petite he was splendidly proportioned but big, lean and strong. The differences fascinated me. The feel of his back muscles moving under his shirt fabric was getting me all hot and steamy.

Somewhere a detached part of my mind was as fascinated by my own responses to this man as I was by the man himself. How strange that an interest I had never felt before was wakening.

He'd moved his scratchy wonderful kisses down to my lowest ribs now. His hands were working at the buttons on my jeans and I was tugging ineffectually trying to pull his shirt up over his head. I was on fire and I was about to give my body up to this man. Goddess forgive me I was about to do it. He was pulling my jeans down my hips and tight as they were they dragged my panties with them. I'd achieved enough success with his shirt that he had to pause his activities long enough to finish the job or it would be in his way.

Holy hell what a glorious sight was revealed then! Lightly hairy and pleasantly tanned his toned torso was unveiled. He'd sat up on my naked thighs to pull his shirt free and almost involuntarily I followed him up to apply my face to his body. Was this heterosexual desire? Was I actually capable of it? Apparently yes! I pressed my face against the centre of his chest and kissed this man's body. Between my legs my desire was a fire that needed attention but I was trapped in the twisted jeans still tangled around my knees.

"Fuck me Jack! Please? I need it? Take me! Teach me how to please a man?"

He didn't need much encouragement. He had to climb off me to free my legs but that gave me a moment to bury my fingers in my exposed pussy as he pulled his own trousers and boxers off. There I was naked before a man with my fingers ploughing over my clit and into my body as his manhood sprang free. What a sight that was too. He wasn't too large. That had been something I'd had a little secret fear about. I'd seen some porno pictures and those men looked huge. Jack's cock was beautiful. About as long as my favourite vibrator and just a little bit broader. He would stretch me open without going uncomfortably deep.

I had a little feeling of relief but that was almost immediately overwhelmed by a powerful and unexpected lust. I wanted to touch this thing, to feel it. I hadn't expected this impulse but it was so much like and yet nothing at all like the toys I had become accustomed to. I needed to know more and I wanted to do something special for Jack to show my appreciation. I sat up.

"Jack would it be ok if I tried a blow job of you? I haven't seen a real cock before? It's beautiful. You're beautiful. Can I try it? I've always secretly wondered what it's like."

That was true. I had been curious. He let out a groan of pleasure that I took as permission because he was guiding it towards my face. Too fast... I flinched a little, expecting unpleasantness as he forced it into my mouth but that didn't happen. To my surprise and relief he'd noticed my reaction and stopped.

"Its ok baby, in your own time."

I don't know if you can really understand how it felt to hear those words. To be allowed to have this experience at my own pace. This was to be another of many first experiences I'd had but it would be the first of my firsts that ever happened on my terms at my pace. If for nothing else I will love my gentle husband for ever for the feeling I had in my heart at that moment.

I kissed the head of his cock. It was warm and a little fluid from the tip smeared on my lips. I tasted it with my tongue. Warm, salty and nothing at all like Claire's fluids. Jack wasn't fully erect though I didn't know that at the time. As my lips touched his head he passed some critical point in the erection process and the foreskin that had covered the tip slid back revealing a dark purple moist knob on the end of his rod. His erection was coming on fast though his cock was not getting any longer, just a fraction fatter and standing up.

This was all a new experience for me and I was so fascinated watching I almost forgot to continue but he coughed lightly and I giggled at the lack of subtlety. I took his shaft in my hands and very gently stroked, it was amazing how the skin moved. As I stroked up the foreskin would pop back over the head a bit, as I stroked down the skin pilled back revealing a kind of ridge at the back of the head. I was worried that I wasn't being gentle enough but Jack's groans were undeniably pleasure.

I opened my mouth and took the head in. I was careful not to scrape it with my teeth but I found I had to open my mouth uncomfortably wide to accommodate his girth. Jack was doing little nudges with his hips. At first it was alarming but nothing bad happened and it was clear he wanted me to take more in my mouth. I'd love to tell a lie now and make myself sound like some kind of super porno star but I wasn't that. I was just an inexperienced young woman and I took as much as I dared but I wasn't brave enough to try deep throat or anything like that.

Still Jack seemed to appreciate my efforts and soon I was bobbing away with my mouth taking his head and maybe an inch or so more with my hands stroking the shaft outside my mouth. I had seen pornos and I was just copying what I'd seen. He tried to pull out of my mouth when he was about to cum but I didn't allow it. I know it was very daring of me but his gentle treatment was already emboldening me, healing the wounded mess of scar tissue that was my self esteem and ego.

I was extremely curious about cum and I sure as hell wasn't going to let my first ever blow job finish without tasting it. I sucked him till he blew and I swirled it round in my mouth with a surprised smile on my face. I liked it! It was much the same as the pre-cum but with a descent quantity I was able to properly appreciate its strange warm goodness.

'Oh my God Jesse! You are so fucking hot! I can't believe I just got sucked off by a Lesbian. Are you going to swallow that? It's kind of weird what you're doing."

I swallowed and laughed at the expression on his face and his obvious excitement at my orientation. I mean honestly what is it with men and Lesbians? Why was the fact that I was gay making this more exciting for him. There I was with his cum in my mouth and fond amusement in my heart. Who was this happy girl? Someone I vaguely remembered from my past perhaps.

His words and the site of his saliva coated cock slowly wilting in front of me rekindled my own desire and I pulled him down on top of me as I lay back on the bed. For the first time ever I felt a naked male body against mine but my inexperience was limiting me. I didn't know what to do. Jack was ready to retake the control now anyway. Perfect!

He pushed himself between my legs and I felt his now semi flaccid wet cock pressing against my equally wet pussy as he began kissing my neck and shoulders and his hands explored my body in ways that only Claire had ever done before. I had a secret hope that he would go down on me but I was too shy to ask and he didn't. Later I would have the pleasure of that experience and it was wonderful but this first time he didn't.

He did know what he was doing though. With his lips tongue and one hand he gave my breasts as much love as they could cope with. He had me squirming in no time. His other hand had made its way teasingly slowly down across my abdomen, over my little ginger racing stripe pubes and found my pleasure button which had already fallen completely and madly in love with him and was obediently rising to the challenge his fingers were presenting. He was driving me wild and my gasped pleasure had him hard again very quickly.

"Are you ready Jesse?"


Hissed between my teeth as my body became his to command, to take, posses and cherish. Most of those privileges had been Claire's; she'd claimed them as rights. Now though I gave them willingly to another, to a man. My betrayal was consummated. He entered me. It felt wonderful, he took his time. He didn't need to, I was very wet but he did and I appreciated it. It was unique, not at all like toys, not even like when Claire used a strap on with me. His cock was a real living part of him and the wonderful slow sensation I was having as he entered me was one half of the experience.

In his eyes and the lust on his face I could see the other half and it made my half all the more intense. He stopped when he was all the way in and kissed me. I took the moment after wards to whisper a breathy thank you to him. He seemed to like that. He began an equally slow withdrawal. It was an exquisite torture to feel his beautiful fat cock sliding out, dragging that big head back down my silky wet inner walls. He thrust in again and though it was only his second thrust the slow deliberate pace was driving me wild and I knew I would have an orgasm soon.

We stayed in that one position, missionary, with our faces just inches apart as slowly he built up a little pace but every stroke was a full stroke, all the way in, all the way out. I kept my eyes glued to his and his eyes locked me in the present. I experienced this; there was no escape to the safe room inside my head. I was a participant. My orgasm was building like a storm on the horizon and I knew it was going to be wild, once before I had felt this kind of intensity in the build up but only once.

It was like this the time Claire punished me with the deodorant can, way back during our basic training. She'd taken me to a place like this but that time I'd passed out and not felt the storm that was to follow. This time that didn't happen. This orgasm I remember. It was so intense it was almost pain. Exquisite pain though. Pain Like I had always needed. My body clamped down on his cock so hard that he stopped mid stroke on a withdrawal. He was in a rhythm so he cried out with some kind of intense sensation but as my muscles relaxed before a second powerful spasm he thrust back in to his full depth and my body locked down again.

He stayed deep inside me this time as my body pulsed. Each pulse was a wave of pleasure so intense that my back arched up even with his weight on me and I ripped a hole in my sheet with my left hand. My right hand was behind his back and I slid it down to his bare buttock where I could feel his muscles clenching in time to my own rhythm. Moments later there was a corresponding pulsing inside me and I could feel his hairy testicles moving between my thighs as he emptied his second load into my body. My eyes shut and for the longest time I couldn't move at all. I was actually paralyzed. Maybe thirty seconds, possibly longer. When I regained control my back was still painfully arched and he had collapsed on me, I fell back against the bed myself and he popped out of me. That was a little painful. We were done but so too were Claire and I. We were done.

Report Story

byUggg© 1 comments/ 3617 views/ 3 favorites

Share the love

Report a Bug

4 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: