My Girlfriend's Dirty Past Pt. 02

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Steve agrees to pursue Helen's dirty desires.
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Part 2 of the 7 part series

Updated 08/09/2023
Created 06/25/2023
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This story directly follows on from part 1 of My Girlfriend's Dirty Past, and should be read first.

As always, my stories are a mix of fact and fiction, or embellishment on true events.

The next morning I woke up feeling a bit fuzzy from the drink. It was about 8.30am and already really bright in the tent. Helen was sitting up and putting on a t-shirt and shorts,

"Morning, how are you." She said with a crooked smile.

"Hmm, OK, bit of a thick head." I said.

"Yeah, me too, I need a shower badly to wake me up." She said picking up a towel and washbag.

"Hang on, Helen, we need to talk."

"Really, I thought everything was cool. Didn't you enjoy yourself last night?"

"Well, yeah, I certainly did. But I wanted to ask you more about all those guys...that...er..."

"That I fucked?" She said, effortlessly finishing my sentence."

"Well, yeah."

"I'd be happy to tell you all, but not now, really I have got to get a shower, but I'm assuming you are happy to carry on."

"Carry on, how do you mean?" I asked.

"Well, we are on holiday aren't we, we should have some fun especially as nobody knows us around here, it's the perfect opportunity."

"Opportunity for what exactly?" I asked to clarify.

"For me to enjoy an extra cock or two."

I swallowed a little nervously, and Helen leant over and put her hand on my cock and gently squeezed my balls through my underwear.

"Would you like that?"

"Yes, I would." I said definitively.

"Good boy!" She answered emphasising each word with another squeeze of my balls,

"I'm off to shower, why don't you see if Dave is alive."

We both chuckled as she left the tent with her towel and washbag under her arm. I just lay there for a few minutes trying to take in all the information. This seemed like a huge shift in our relationship and one I had not anticipated at all. I smiled gently thought about the events of yesterday and of what sort of a girl my girlfriend was turning out to be. It still seemed a bit unreal. Had she really been fucked by 45 different blokes, Christ! What a slut.

I sat up and groaned as my head ached and made my way to the tent opening and stuck my head out. It was another beautiful day, bright and sunny, which made my eyes hurt a bit.

"Dave!" I called out to my friend in the next tent. No answer.

"Hey, Dave!" I tried again a bit louder.

"What?" Came the slightly irritated reply.

"You awake?"

"I am now, you wanker!"

I laughed and crawled across to his tent and stuck my head in. Dave was flat on his back and stark naked. I was a bit surprised that he wasn't in his sleeping bag although it was really hot, I suppose, but what most surprised me was he had a huge erection. His circumcised cock was sticking straight up his belly, I looked a lot bigger than mine, at least 8 inches long, with a big head like a ripe strawberry on top. I couldn't believe how massive his cock was, and I couldn't help but stare at it momentarily in admiration.

Dave looked up suddenly and sleepily said,

"Oh, hi".

He sat up quickly when he realised I was there and put his knees up to cover his massive hardon.

"Oh, sorry was half asleep." He said.

I sniggered and said,

"Nice dream, was it?"

"Hmm, something like that."

He tilted his head a little and looked behind me to our tent and asked quietly,

"Is Helen there."

"No, she's in the shower."

"Ah, was dreaming of her!" He said cheekily.

"Yeah, it looked like it." I said, laughing again and motioning with my eyes to his crotch.

We both laughed together.

"Bloody hell, mate." He said.

"What?" I asked.

"Your girlfriend, I mean I know you said she was a real goer but shit! I didn't realise she was such a..." He suddenly trailed off as if he couldn't find, or didn't want to say the word, so I finished it for him,

"Slut!"

"Yeah, dirty fucking slut!" Dave added.

"I know, it was a bit of a shock."

"Too right, I could see by the look on your face when she told you she had fucked 25 blokes!"

"Oh, didn't you hear our conversation last night in the tent?"

"Well, I did hear quite a lot of stuff, she's not quiet when she's in the mood is she! And I heard her speculating about the size of my cock, which was nice to hear I must say! And then her begging to be fucked!"

Dave said laughing heartily.

"Oh, sorry about that."

"Don't apologise, Steve, it was lovely to hear she was thinking about me, and she was right by the way, I was having a lovely wank thinking about her gorgeous little titties, not to mention, that arse! Oh, and for the record, I would be more than happy to watch you two fucking."

I laughed at that, but blushed a bit, Dave had obviously heard a fair bit not surprisingly as Helen refused to keep her voice down last night, I'm pretty sure she was getting off on it knowing Dave could hear almost everything.

"Oh, and I'm not sure if I heard right but, did you come on her?" He asked.

"Yes, she asked me to come on her face!"

"Fucking hell, nice!" He said, obviously very excited about the idea.

"But did you hear the real bombshell, about all the guys she let fuck her?"

"Well yeah, I was there when she told us both mate. Blimey, how drunk were you last night, she has let 25 different blokes fuck her, she's a total slut!...My kind of girl really!" He said laughing again.

"No, no, you didn't hear what she told me in the tent, Dave!"

"Oh, shit, was she just bullshitting! I knew it, she was just cockteasing."

"No, Dave. She told me she hadn't fucked 25 blokes, it was more like 45! She actually lost count after that!"

"Forty-fucking-five!"

I sniggered again, "Yes, 45!"

"Bloody hell, what a dog!" Said Dave automatically, then he turned to me looking slightly more serious and said somewhat concerned,

"Are you OK with that?"

"Well, I must admit I was really freaked out when she first came out with it, it felt really humiliating, and I was pretty embarrassed that she came out with it in front of you as well, in fact it felt even more humiliating, but to be honest she's right that we weren't together then so what does it matter really? But when we were discussing it together in the tent last night, although she didn't go into much detail, I couldn't help but get really turned on by it, I think I had one of the biggest orgasms of my life."

"Really!" Said Dave.

"Yeah." I said thoughtfully, "She thought it was really funny, and she was tormenting me last night, like I said she wouldn't go into much detail, but just kept going on about all the men that had been up her pussy, and the more she talked about it the harder my cock was."

Dave looked at me shifting his sitting position to get slightly more comfortable and subtly pulled his sleeping bag over his legs and adjusted his cock, and then asked,

"Hmm, I'd certainly like to hear a few more details if she fancies a chat!" Said Dave cheekily.

"I'm sure she'd be happy to talk more when she's had a couple of drinks". I said mulling it over.

"So would you like her to carry on then?" Asked Dave.

"What, fucking other blokes?" I said.

"Hmm." Said Dave.

I took a deep breath as I considered it and looked Dave in the eye and said,

"Well, yeah, I've already agreed at least on this holiday she can, and as long as she stays with me, I think it could be a real turn-on if she fucked other men."

"Hmm, nice!" Said Dave, very happy to hear that I was fine with it.

"Well, I think she's got the hots for you mate, I think she would be well into it!" I said,

"That was quite a view she gave me when she was on all fours leaning in the tent yesterday, I must say I would love to see more of that gorgeous arse of hers, the only thing that could improve that view would be if she were over my knee with her knickers down feeling the palm of my hand tanning those cheeky buttocks!" Said Dave very enthusiastically.

"Wow, really, you'd like to spank Helen?"

"Oh god, yeah, I would love that!" He continued.

We both laughed again.

"I think I'd like to see that too, Dave!" I said, giving him a wink.

I heard Helen calling from down the hill and looked over to see her returning from her shower. She was in a little blue vest top and her very short denim skirt again and sandals.

"Oh, Helen's coming back. We should go and get showered. We're thinking of heading down to the beach this morning."

"OK, great, with you in a minute."

Chapter 2

Dave and I got back from the showers and Helen was just putting a few things in the car ready for the beach.

"I thought we should go in the car because the beer chiller is a bit heavy and we also want to take the wind cheater, as well as some food, so we might as well park near the pub and walk from there." Said Helen.

"Yeah, good idea." I agreed.

Helen opened the boot and bent over putting some bags into the car, pausing to adjust the seat at the back to give us more room. She was bent right over again with her pert little bottom shifting in her tiny denim skirt. Both Dave and I stood there absentmindedly staring at her arse as she waved it invitingly in mid-air, her skirt just a fraction below her panties, (so near but so far!). I looked at Dave who was already way ahead of me as he glanced back and pursed his lips, sliding his tongue across his mouth. She backed out again and turned to look at us both as we all stood briefly staring at each other blankly. I think Helen suddenly cottoned on to what was going on and just smiled at us both wryly and said,

"Nice and clean after your shower boys?"

We both just smiled back at her. I think she had made a little display of her arse deliberately, dirty girl.

We finished packing and I noticed Dave feasting his eyes on my girlfriend in her tight vest, still no bra, her nipples pointing obviously through the thin material, her short skirt and long bare legs. I got in the driver's seat, as I was the only driver amongst us and Dave got in the back. Then Helen surprised us both by insisting she got in the back with Dave.

"But there isn't much room with all the bags and stuff, Helen." I said.

"It's OK, I can sit on Dave's lap." She said briskly.

She opened the back door and spoke to Dave,

"You don't mind do you Dave?" She asked giggling a bit.

"Certainly not, Miss, it would be my pleasure!" Said Dave, most amused and no doubt very pleased with the idea.

"Well thank you, Sir!" Helen replied.

I looked back at the scene. Dave is a handsome dark-haired guy, and pretty tall at 6' 4" and has long legs, so he had to sit with his legs apart to avoid his knees pressing into the front seat. Helen managed to plonk herself down right on his bulge and nestled her arse against his cock, as she did this, she quite deliberately ground her tight pantied arse and pussy into his cock. Her skirt was so short that her knickers and some of her bare arse cheeks were pressed against his bulge, and well as her naked legs brushing up against Dave's in his shorts. The shock of Helen sitting straight on his cock obviously surprised Dave a bit and he automatically put his hands on either side of her hips as she was in danger of crushing his balls.

"Oh, sorry Dave!"

Dave breathed out briefly and then let her settle by shifting her weight a little in his lap and said,

"No, that's absolutely fine, thanks." He said with a smile, keeping his hands on her slim hips I noticed.

Helen put her arm around his neck and said,

"You're welcome." And offered a cute little giggle, and another little wriggle of her arse just for good measure.

Christ, what a tease she was, I thought Dave might actually come in his pants before we got to the beach. It was only a short drive luckily, or unluckily, depending on how you look at it I guess, and I drove with a big grin and a bit of a semi too as I kept glancing behind me alerted by the sound of assorted giggles and squeals, mainly from Helen as she took every excuse to bounce up and down on the rapidly growing bulge in Dave's shorts.

"Blimey, it's really bumpy isn't it!" Helen suddenly called out.

"You're kidding aren't you, the road is smooth as a baby's backside here." I called back.

"No, I mean my seat, Steve!" Replied Helen giggling again teasing us both.

Dave and I both laughed out loud as I tried to keep my eyes on the road.

Finally, we made it to the car park by the pub. I climbed out and opened the back door for Helen and Dave. They were both smiling broadly looking like they had had the time of their lives on the short ride. Helen lifted her legs and shifted her torso towards me whilst managing to grind down her arse one last time against Dave's by now, massively stiff cock, and he let out a little puff of breath. Helen smiled up at my face with a cheeky grin and winked at me, then deliberately parted her legs as she lifted them out the car giving me a nice view of her white panties, with a big red cherry on the front. She knew these were one of my favourite pairs of her panties, and she smiled again as she recognised the acknowledging smile on my face.

Helen finally planted her feet on the ground, and I held her hands lifting her up and out. I looked down at Dave who looked a little shell shocked as he clearly pushed his big cock to the side of his shorts and climbed out the car with a little difficulty. Helen and Dave were beaming at each other as we collected all our gear from the car and walked down to the beach chatting and admiring the view.

The beach was really nice, a large sandy cove with gentle cliffs on one side dotted with houses and cottages, and higher more dramatic cliffs on the other with about a quarter of a mile of beach in between. Not too many people around as it was not yet the school holidays. The sun was pretty bright with just the odd cloud for cover. We headed off towards the right and the seclusion of the higher cliffs. We dropped our things on the sand and Helen and Dave started to put up the wind cheater, which was more to give us a bit more privacy behind us, leaving the sea view in front and a nice gentle cooling breeze coming from it.

"At least we won't have to search for a mallet to get the posts in the sand!" Said Helen cheekily as she looked down at Dave's crotch, the remnants of his hardon still visible.

Everyone laughed again and I wondered if she could be more overt with her flirting, here she was openly commenting on my best friend's cock. Dave looked pretty happy about it though.

When we had just about sorted everything, Dave suddenly announced,

"Last one in the sea is a wanker!"

He then whipped down his shorts revealing his tight swimming trunks underneath, the outline of his cock clearly visible and then turned to run towards the sea laughing loudly.

"Oh, bloody hell, he's already got his trunks on, bloody cheat!" I shouted after him.

"Wankers!" He called back to us.

Helen and I both sat on our blanket laughing at him as he charged onwards the hundred yards or so and splashed into the gentle current.

I looked around for my swimming trunks and started to get ready to join Dave when Helen spoke,

"Dave has a massive cock!"

"Yes, I know, it's fucking huge!" I answered.

"Oh, you've seen it?" Said Helen immensely curious to hear more.

"Just this morning actually, by accident. I went in to wake him up and he was just lying there naked with a huge morning hardon."

"Hmm, that's sounds nice, what was it like? Is it bigger than yours."

I felt a bit strange describing another man's penis to my girlfriend, but I knew it was only a matter of time before she got to see it and get to grips with for real.

"Yeah, it's bigger than mine, and circumcised, with a big strawberry shaped shiny head. I reckon it's at least 8-inches long, and a pretty big girth too."

"Oh wow, that sounds delicious!"

Helen made a slurping noise and added,

"I'd love to suck on Dave's big cock."

I smiled back at her.

"Nice."

"Would you like to see me with your friend's big cock in my mouth?" She asked, pushing me further.

"Yeah, I'd really like that." I said slowly, picturing it in my mind.

"And would you like me to swallow all his come, or maybe beg him to spurt all over my face like a true dirty slut would?"

I cleared my throat a little from the tension, I knew we were now crossing a boundary, and I continued a little nervously,

"I'd like you to beg for his come all over your dirty slutty face, Helen. I want to see your face absolutely covered in his come!"

Helen smiled looking very pleased with herself, and with me.

"Is the right answer!" She announced.

"Now go and join him, cool down a little bit in the water, I'll see what I can do to entertain you both a bit later." She added.

I went off to find Dave in the water feeling pretty excited about Helen's promise and we both swam and messed about for a while. It was refreshing but soon got a bit cold, so we headed on back to Helen after about 20 minutes.

Helen was reading a book and having a can of cider when we got back reclined fully on the blanket, her short skirt had ridden up about an inch above her panties, leaving them just visible and I noticed Dave look straight down between her legs as we got close.

"Good swim boys?" Said Helen lazily.

"Yeah, it's great, a bit chilly after a while though, we were waiting for you to join us." I said.

"Well guess who forgot to bring her bikini, maybe I'll go in a bit later, I could just wear my knickers I suppose."

"Yes, sure." I said, looking at Dave as we both smiled.

We both sat down and for the next hour or so had a couple of drinks. It was fairly quiet on the beach at least in our area still, with only one or two people wandering past every now and again. Dave was stretched out on his back next to Helen, his wet trunks clinging to his penis as they slowly dried in the sunshine.

"Boy it's getting really hot now." Said Helen, "You don't mind if I take my top off do you Dave?"

Dave's face immediately pricked up, as did my ears.

"Erm, no, of course not...I don't mind at all." He said turning his head first towards her and then to me and smiling.

"Yeah, there's hardly anyone around anyway, it's fine." I said encouraging her.

"Cool." Said Helen.

She sat up as both Dave and I watched intently as she pulled her vest up over her head and placed it behind her baring her lovely small breasts, showing them off for me and Dave, but I guess, mainly for Dave. Dave's eyes lit up as he stared at them, and he swallowed slightly nervously. I felt a rush of excitement at my girlfriend allowing my friend to see her breasts. She looked down at Dave who immediately averted his eyes.

"It's OK, Dave, you can look at them if you like." Said Helen quietly, calmly.

"Ah...erm, right." Said Dave hesitating but looking back at her breasts, his hand shielding his eyes from the sun in an effort to see them properly.

"There's not much to show really. God, loads of the boys at school and even at the campsite last summer used to take the piss out of me because my breasts are so small."

"Really!" Said Dave, "but they're gorgeous!"

"Oh, thanks Dave!" Said Helen, sounding genuinely flattered, and shifting her shoulders around looking down at her small boobies.

Dave and I just marvelled at the sight as she moved them around for our obvious delight. She absentmindedly poked her finger around the areola of her right nipple adding,

"My nipples are quite sensitive though, and I think the sun is waking them up." She said, as she continued to play with her nipples, moving between each breast and toying with them casually.

Helen suddenly averted her gaze from her own breasts straight to Dave's trunks where his cock was stirring with obvious vigour.

"Wow, Dave, you do like them, don't you!" She said still staring at the movement between his legs.

Dave quickly placed his hand down to his cock and attempted to hide his swelling member.

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