My [f]irst time [cheating]… I feel bad about it now, but I know I needed it then

I’m writing this post partly because I need to get it all down in writing so I can think clearer about it, and partly, if I’m honest about it, because the experience still turns me on a lot and I want to share it with other people. Please reserve your moral judgement – I’m doing enough of that to myself! I’m just going to tell you what happened, in all the steamy detail, and I hope you’ll enjoy it and tell me what you think.

My name’s Katie. I’m a 24 year old girl doing a PhD in English Literature at a well-known college. I might as well describe what I look like – I’m 5″8, have medium length, straight blonde hair and a big smile, and I’m slim and athletic. Since I’m sure you’ll want to know, I’ve got perky, medium-sized breasts, just the right size for guys (or girls, for that matter) to cup in their hands.

I have a long distance boyfriend whom I’ve been with since I was an undergrad. I care about him and when he visits we have a very vigorous sex life – and doesn’t my roommate know it! – but I’ve been finding it hard during term time when he’s away. I’ve never wanted to cheat, and everything that’s happened here was basically a mistake, but I’d be lying if I said it wasn’t a mistake I enjoyed making.

One of my best friends at college is a guy called Steve. He’s a Physics grad student, tall and handsome. He’s got stubble and wavy brown hair, and we’ve been close since Orientation week. Over this semester we’ve spent many nights watching films together and talking about everything, from politics to our romantic lives, and we also go running together on Saturday mornings. Steve looks amazing in running clothes, and I have to say I enjoy the feeling of him seeing me in my jogging shorts and sports bra. Over the course of the semester I’ve allowed my mind to wander sometimes and imagine what he’d be like in bed, particularly as the work-load started making me more and more stressed and I started looking for a release. I Skype my boyfriend often, but that’s not good enough for weeks on end, and I started craving a man’s touch on my body.

Well, the crisis point came last week, when we were sitting on my sofa in my room, watching Games of Thrones together. We’d been doing this for weeks, and we’d always been amused by the nudity and often talked about things like the difference between art and porn, and how realistic the depictions of sex were. But this time the sexual tension seemed higher than usual. We’d just come back from a late-night run, and there was a heady atmosphere of sweat and hormones in the air. I had changed into a medium-length blue dress, and he was wearing his lounge pants and a T-shirt. On the screen the action was becoming increasingly sexual, and I could sense that we were both getting aroused.

I looked over at Steve and smiled. ‘Here’s my daily reminder that I haven’t had any in two months!’, I joked. Steve grinned, and I tingled slightly under his gaze.

‘Imagine how I feel…’ he replied. Steve had been single since the start of the year, and except for a few mediocre Tinder dates hadn’t seen any action all semester.

Something about his reply turned me on, and I teased him, surprising myself with my slightly flirtatious language. ‘Well, you can at least take care of yourself, can’t you? I mean, that’s the only way I manage it…’

Steve smiled knowingly at me, and my heartbeat quickened. ‘Do you mean, do I jerk off?’, he said. ‘Well, of course I do… I’ll be doing it tonight probably, as soon as I get back.’

‘Why not do it now?’, I suddenly blurted out. I couldn’t believe what I was saying. Somehow my stress, sleep deprivation and general horniness were making me impulsive.

Steve looked at me with wide eyes. ‘Katie, are you serious?’, he said.

‘Sure… we’re close friends’, I said hesitatingly, more trying to convince myself than him. It was too late to row back on what I’d said, and although I didn’t want to cheat on my boyfriend I was already trying to justify it to myself internally. Watching someone masturbate isn’t cheating, surely? I mean, I’d watched people do far more in porn and that definitely wasn’t cheating.

‘I wouldn’t mind if you took care of yourself now….’ I said softly, blushing and averting my gaze. I looked down at his lap, and the unmistakable outline of his growing erection was emerging through his pants. I felt a familiar warmth and tingling sensation between my legs, and I added cheekily, ‘Besides, it’s not like I’ve never seen a cock before.’

That did it for both of us. Saying that out load made me flush bright red, and I could feel myself growing wet. Steve took a sharp intake of breath and looked at me with a hunger I hadn’t seen before. He hesitantly slipped his fingers under the waistband of his pants, looked at me once more as if for confirmation, and pulled them down to his knees.

From under them sprang out probably the most gorgeous penis I have ever seen. It was large, certainly, but what was really impressive was its thickness and the size of its well-developed head, which was the same colour as his lips. On his meaty tip glistened a drop of clear liquid. At the same time, I caught a sharp whiff of a musky, manly aroma, tinged with sweat from our run, but in a hot, rather than an off-putting, way. It was quite overpowering. I could feel my panties growing wetter, and I lusted after him.

Looking at me nervously, he slowly started to rub his shaft, groaning slightly as he did so. He paused Game of Thrones, and I stared at him hungrily. ‘You look… very sexy, Steve’, I murmured.

‘Do you… you know… want to do the same?’, he whispered to me. I thought about it. Touching myself in front of a friend wasn’t the end of the world. I’d done it with female friends before and my boyfriend hadn’t minded, and I’d even done it once or twice on webcam to strangers on a chatroom when I was really horny, though I had felt bad about this afterwards. I wasn’t sure what to do, but my exhibitionist instincts were taking over. I put my hands under my dress and slowly pulled my panties down to my ankles. In the middle was a warm patch of moisture, and I enjoyed the feeling of cool air in-between my legs.

Steve was rubbing faster now, and I watched as he pumped his hand up and down his engorged manhood. He stared into my eyes, and then looked down at my chest, and down to the panties around my ankles.

Suddenly I decided I wanted to give him a show. I placed my hands on the hem of my dress, and with one movement lifted it up over my waist, revealing my naked legs and pussy. I turned myself towards him and spread my legs wide. Steve groaned and started jerking harder, and I tentatively made circles over my clit with my fingertip. I slid my fingers up and down my soaking pussy lips to get them wet and then started touching myself more confidently, making eyes with Steve and feasting on the sight of my friend pleasuring himself right next to me.

We continued this for some time, I have no idea how long. I could slowly feel the wave of an orgasm approaching, and I bit my lips in an effort not to shout out and wake my roommate, who was sleeping next door. Then I came hard, moaning loudly. Steve looked into my eyes and smiled, then looked anxiously towards my roommate’s room.

‘I’m about to cum too’, whispered Steve, and he continued pumping his cock up and down. I was beside myself. Suddenly I threw all caution to the wind, and forgetting about my boyfriend, I simply said ‘Steve…’, and leant over his lap. He took his hands off his cock and unzipped the back of my dress, unhooked my bra and gently cupped my breasts in his hands. I slowly took the first few inches of his penis into my mouth, feeling its smoothness and warmth with my tongue, and enjoyed its musky, slightly salty tang. Cupping his balls in one hand, I rubbed his shaft with the other. I made my mouth as wet as possible, and started giving him the slurpiest, hungriest, most uninhibited blowjob I have ever given sober.

Suddenly, he gasped. His cock twitched, and a thick jet of cum shot to the back of my throat. I could feel it all over my tongue. Then there was another. And another.

I barely had time to swallow, and drops of cum dribbled down my chin and onto my breasts. I took his cock out of my mouth to lick my lips, and a final few pearly drops oozed out of his tip and dripped down the head of his penis. I leant over and squeezed them out, sucking him dry and giving his tip a quick kiss.

‘Oh my god, Katie’, he whispered, ‘that felt amazing.’

I kissed him briefly on the lips, and we hugged, more as friends who have just experienced something amazing than as lovers. Steve got me some water so I could rinse out my mouth, and we cuddled for an hour or so in our underwear, chatting softly and enjoying the evening together.

We talked about it the next day and agreed it was a wonderful, one-off thing. We’re still friends, and now Steve has a girlfriend, whom I really like.

I haven’t told me boyfriend, and I do feel very guilty about blowing my best friend behind his back, but please don’t judge me too harshly. I will try very hard not to do something like this again. But after a long, stressful semester, this was exactly what I needed, and I thoroughly enjoyed every second of it.

Source: reddit.com/r/gonewildstories/comments/829m3z/my_first_time_cheating_i_feel_bad_about_it_now