Angela’s First Time With A Much Older man

"The first time I watched another guy fucking my girlfriend"

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This is a true story about a girl I used to date, and eventually married, many years ago. The events here took place a few months before David came onto the scene for us, and looking back, I believe served as a pre-cursor to me being so amicable about him fucking her, for so long.

Angela was nineteen at this time, and I was twenty-one, we had been dating for a few months and were relatively happy, and we planned to buy a house together in time.

Angela was a very pretty girl with soulful green eyes, a wide mouth, beautiful glossy dark hair, and a small petite frame.

I say relatively happy, as I always had a nagging feeling she wanted something more sexually, something darker, perhaps more taboo. I couldn’t put my finger on it however until the events below unfolded.

She was 5’2” tall and always very slim and slight despite being so short. Angela had a gorgeous tight little ass and perfect 32a cup breasts that seldom required her to wear a bra.

Angela was highly sexed during our time together and though submissive in the bedroom she could also be quite wild and abandoned when the mood took her.

She dressed sexily too. She loved wearing short skirts with high heels and tight little shift dresses if we went out together anywhere decent. With great legs and a small tight bum, Angela drew admiring looks from men often which always gave me a thrill.

We both had good jobs back then and also a good social life with close friends. Her work, however often arranged social events with employees and their respective partners welcome.

During this time we went to many works parties, Halloween nights, Christmas parties, and the like.

She once told me about a guy she knew through her job, who made it obvious he had the hots for her. I knew she often saw him for lunch during the week and she told me things never went beyond flirting and suggestive conversations, yet I could sense she found him attractive, despite us being firmly attached.

Several months went by, and one night we were chatting about Martin, the guy in question, and I asked her more about him. She said he was forty-four, and a bit of a cad with the girls throughout the company she worked for, and that his reputation was well known.

She half-jokingly said to me one night, ‘How would you feel if I let him have sex with me?’ I don’t think she expected a genuine reply from me, or perhaps she thought I would shoot her down in flames but I simply said, ‘Why, would you like to then babe?’

After a few minutes of silence she confessed to me she had thought about it many times but didn’t want to hurt me. ‘I would never cheat on you,’ she added, ‘Not for anything.’

We hugged and kissed, and I said, ‘I know you wouldn’t my love, you do not need to say so.’

There was an awkward moment of silent pause between us, so I took the plunge and said, ‘What if I said I wouldn’t mind if he did fuck you?’

She stared back at me, her green eyes wide with apprehension, ‘Are you serious?’ she asked.

‘I would not have said it if I wasn’t,’ I replied.

I could tell she still thought I was joking so I pipped in with, ‘Look darling I know you fancy him, I knew you did ages ago, and I know he wants you. It’s only sex, not love and I would be lying if I told you the thought of him fucking you did not turn me on,’ I added.

Angela listened and looked at me, her face showing surprise and she was flushed, ‘Babe I can’t believe you are saying this, do you really mean it?’

‘Yes, darling I do,’ I said, ‘I would truly love you to let Martin enjoy your gorgeous little body.’

‘I don’t want an affair with him,’ she said, ’Nothing like that, but just a bit of occasional fun.’

’Then go for it sweetheart,’ I said, ‘Enjoy yourself on the side so to speak.’

‘You realise his age,’ she replied, ‘Of course I do,’ I said. ‘But be honest, isn’t that part of the appeal? The naughtiness of it, the taboo?’ I added.

‘Yes it is very much so,’ she replied.

She told me Martin, had wanted her for some time, and he had told her he preferred submissive younger girls to women of his own age.

She said he was very explicit about his sexual kinks and what he enjoyed did excite her a lot.

We talked at length about it that evening, and more over the coming week. A few weeks went by and she told me about a birthday party coming up that was planned with her work colleagues. It was for the coming Saturday evening and employees and partners were all invited. It was being held at a venue not far from where we lived that had a dance floor and bar, and food was being laid on as well.

‘Will Martin be there?’ I gingerly asked her over dinner that evening.

‘Yes he will,’ she said.

We both looked at each other and smiled, I saw a spark in her eyes and almost together we said, ‘Maybe a good chance to be naughty with him.’

‘You really want me to don’t you?’ she said, as put down her knife and fork and looked right at me.

‘I do my love, I mean it,’ I said. ’No strings, just enjoy yourself with him,’ I added.

We kissed deeply, and looking into my eyes she said, ‘Darling thank you.’

Saturday arrived and as the evening approached, Angela had gone upstairs to shower and start doing her makeup and get dressed for the party. She had bought this beautiful outfit, very much of the time back then.

It was white and consisted of a long straight tight skirt made of thin silky material with an asymmetrical hem, that was long on one side but went higher on the other. The hem was trimmed with white lace, Cindi Lauper eat your heart out!

The top was styled to look like a fitted jacket, long-sleeved with three buttons on the front, that wrapped round double-breasted fashion. This was also trimmed with white lace.

The whole look was of delicate femininity and elegance. Angela partnered the outfit with these amazing metallic gold high-heeled court shoes, the same heels she wore a few months later during our first visit to an adult cinema together. The shoes were, again very much of the time.

‘You look incredible,’ I told her as she was styling her hair.

’Thank you, darling,’ she said.

‘What do you have on under it?’ I asked her.

‘Bra and knickers both in white,’ she replied, ‘Why?’

‘I dare you to go naked under it,’ I said.

She giggled and said, ‘You pervert. Really? You want me to wear nothing underneath?’

‘Go on you minx, I dare you,’ I said.

She flashed me a radiant smile then reached under the skirt, sexily slipped her white knickers down her legs, and dropped them on the bed. She then unbuttoned the top, slipping it off her shoulders, and reached round to un-clasp her bra which then ended up on top of her knickers.

After re-buttoning the top, she smiled at me again and said, ‘You corrupt me you know that.’

We both laughed and I replied, ‘Hopefully it will be Mark the does that my love.’

Without a bra on, the low front of the top showed plenty of cleavage, even though Angela was quite small in that department her tits were pert and firm.

However, when I looked more closely at the skirt it was quite obvious she had no knickers on. I could see the shape of her bum through the back and at the front, I could see a hint of the shape of her pussy, despite her keeping herself always shaved back then.

I told her these points and she simply said, ‘Well you dared me so…’

Angela looked stunning that night and oozed sexuality, her makeup was perfect, and she partnered the outfit with a delicate gold necklace and matching earrings.

We called a cab and sat around downstairs waiting.

I had to come right out with it so I said, ‘I think you know who is going to be blown away with how you look tonight babe.’

She smiled back at me and said, ‘Do you think so? If he makes a move on me shall I go along with it?’

‘I think you should make it obvious to him tonight that you are up for some fun at some point yes,’ I said.

‘If it’s what you want then I will,’ she said.

The cab arrived and we were soon on our way to the party, on the way there I could not help placing my hand on her leg and I teased the delicate lace hem a little higher up her gorgeous legs. She did nothing to stop me but sat there smiling to herself.

I glanced at the driver who was casually looking in his rearview mirror and smiling at me. I slowly lifted the skirt hem higher above her knees, as I did so, Angela parted her legs slightly looking at me. I teased the hem a tiny bit higher, and she just sat there still looking at me.

I glanced back at the driver who was switching between the road ahead, and the erotic view he could obviously see in his rearview mirror.

We eventually arrived at the venue, and I paid the driver, ‘Gorgeous girl you have there my friend,’ he said with a grin on his face. His gaze followed Angela’s legs in those gold heels, as she swung them out of the cab and stood up waiting for me.

’Thanks, yes she is, I am a lucky guy,’ I replied.

At the party the atmosphere was great, people were chatting, drinking and dancing. As we mingled it became obvious people had noticed how semi-transparent her white skirt was and what was missing under it.

Martin came over and said hello to us both, then went to the bar and began chatting with some other people, so Angela and I took a table, then went dancing for a while. I could see him by the bar looking at us, or at Angela, I should say.

‘You are being watched from the bar,’ I told her.

‘I know,’ she replied with a naughty look on her face.

As we danced, Angela made a bit of a show with the lace skirt and she grabbed the hem lifting it higher up her legs and sort of swayed it from side to side as she danced. As much as I enjoyed this, I knew it wasn’t for my benefit and I could see Martin at the bar staring and smiling at her.

He and I exchanged glances, and pretty soon I told her I needed to use the toilet, she nodded and carried on dancing. Upon returning from the toilet she was no longer dancing and had moved over to the bar and was chatting with Martin.

I picked up my drink and sat back at our table and watched the two of them. Every now and then either she or Martin, would turn and look over towards me then carry on talking. I had no idea what they were saying of course but I had a pretty good idea.

After about twenty minutes or so, she picked up her drink and walked over to me. She looked so sexy in the white outfit and those gold high heels made her legs look incredible.

As she walked towards me the light from the bar area was right behind her and it illuminated her body through the thin white material of the outfit. Anyone else watching this would be very aware she was naked underneath.

Right then she looked as sexy as I had ever seen her.

She came and sat beside me and whispered into my ear, ‘I am going outside for a minute with Martin to have a cigarette. Is that ok with you babe?’ she asked me.

‘You go, darling, I’ll be here when you come back in,’ I said.

‘I might be a while,’ she said with a wicked grin on her face.

With that we both smiled at each other, then she walked back towards the bar and a waiting Martin, who took her arm to lead her to the way out.

I sat for a while drinking and checking my watch. It had been about ten minutes, so I got up and casually walked towards the exit they had left through.

It was very dark by now but there was a bright moon beaming down through the cloudless night. I looked up at the stars and wondered which way she and Martin had gone.

Walking around the side of the building silently I noticed there was a sort of boarded-off storage area for chairs and Summer tables, and it had a clear Perspex-style roof.

As I drew closer, I started to hear faint voices. I soon recognised Angela’s, so I stopped and went wide around some parked cars until I ended up hiding in the shadows, right next to a big white caterer’s van.

My eyes slowly adjusted to the reduced light, and as they did so I could see her and Martin standing under the Perspex canopy. He had her against the side wall and they were standing close together, his hands around her waist.

She looked so tiny standing next to his six-foot height, even in those very high gold heels. I could feel my heart now pounding in my chest as my mind reeled at what I was seeing. Making sure I kept my breathing shallow, I knelt and froze to the spot, watching intently to see what would happen next.

I could see a couple of cigarette butts laying on the floor, so they had obviously been smoking, but I was hoping things would get a little smokey between them. I couldn’t hear what was being said, but it seemed to be mostly from Martin and Angela was shaking her head, side to side. He spoke some more, and she did it again.

Then he pulled her to him and grabbed her head in his hands kissing her deeply. I watched in awe as she slowly brought her hands up and pulled him closer, their kissing now much more passionate. After some time, they became locked together in frantic lustfulness, kissing more urgently now.

I watched open-mouthed and almost holding my breath as slowly Martin’s hands moved round to the front of her white top. She quickly grabbed his hands and words were exchanged but he pushed her hands away and back to her sides.

They stood there kissing as he slowly began to undo the buttons of the top, Angela, I think now resigned to the fact that he was going to undo the top and expose her naked tits.

I couldn’t take my eyes off what was happening and the realisation then hit her that he was going to slip the top off her shoulders.

Again she tried to stop him and I overheard her saying ‘No, Martin, not here.’

He ignored her and for a second time pushed her hands down a bit more forcefully. I could almost see her trembling at that moment, and I could only try to imagine what was going through her mind.

Skilfully, Martin slipped the lacy white top completely from her body and placed it on top of his folded jacket, on the top of a Beer barrel.

She stood there now in her heels and the white skirt as Martin caressed and kissed her tits neck and shoulders. I could see she had her head bent backward and could hear soft moans as he enjoyed my girlfriend’s now semi-naked body.

After about fifteen minutes or so, Martin then began reaching around to Angela’s bum and his hands were then caressing her ass through the thin white skirt.

My eyes were well accustomed to the moonlight now and Angela’s naked top half was clearly lit before me as Martin groped her bum and kissed her lips, neck, and shoulders again. Then his right hand stopped and began undoing the single button on the back of the skirt.

Quicker this time she reached round and grabbed his hand and I clearly heard her saying, ‘Stop it, you can’t.’

‘Oh I can, and I am going to babe,’ he said.

A brief struggle ensued but Angela could see-I think- she was fighting a losing battle with Martin’s hands.

The button was now undone he turned his attention to the little zipper at the back, and slowly as I stared in disbelief he slid the zipper down her bum, the back of the skirt parted and he eased it down over her bare bum, where it fell silently to the floor.

I could see Angela frantically looking around to see if anyway else was outside, but the pounding music from inside the venue must have reassured her that they were alone.

She stepped out of the fallen skirt, Martin picked it up and placed it where he had earlier placed her top.

I was now transfixed at the sight before me. My girl was now completely naked apart from her gold high heels, with Martin feasting his eyes on her wonderful little body.

Slowly I could see her start to relax and enjoy what he was doing to her.

I have never understood young girls being self-conscious about being naked in public, especially with a body like Angela had. She had her hands around his head again and was kissing him as he groped and caressed her naked body before my eyes.

Slowly she started to kneel and she began pulling and tugging at Martin’s trousers.

He reached down and unzipped himself and her delicate fingers found what she was looking for so urgently. His already hard cock sprung out before her face and without pause, she engulfed it with her lipsticked mouth.

I watched her sucking and licking his swollen cock and could also feel my own cock getting harder by the minute. Angela used her beautiful mouth and hands to slowly work him into a frenzy, and I could hear him moaning and gasping.

Eventually, he just grabbed her head with both hands, and furiously fucked her mouth by jerking her head back and forth on his cock. She steadied herself, by holding his thighs with her hands as he did this. Watching this was simply incredible!

If there was a signal, I missed it as Martin suddenly grabbed her, pulling her into a standing position, he then spun her round so she faced the wall, and just as quickly he grabbed her hands, and before she could react, he had them both together in his left hand. He then pulled her hands up high above her head, his other hand was now working his rock-hard cock ever closer to her.

Using his feet, he pushed her heels apart, a little more, then further. Her bum looked white and pert as he readied himself to fuck my gorgeous girlfriend right there, under the moonlight. She then bent her head back as Martin entered her from behind, no condom, he just took her there and then. Angela made no effort to stop him now, despite him fucking her bareback. Knowing as I did that she wasn’t on the pill at that time, this surprised me but she seemed to have dismissed all thoughts about that as he fucked her.

I stayed hidden in my hidden position as he fucked her, slowly at first then built up to a fast urgent pace. The two of them were moaning in unison and Angela began her usual soft gasps that she often did during sex.

I thought then of her safety as he looked like he was building up to cumming inside her, but then he stopped, pulled out, and re-positioned himself, using his free hand he guided his cock at a higher angle.

I knew what was to come as Angela gasped and said, ‘Oh my god, oh fuck!’ as he began sliding his glistening cock into her bum. Slowly he inched further into her ass, and she had her head fully back as he was kissing her neck at the same time.

She gasped much louder now, as Martin entered her little bum fully. He had to put his hand over her mouth as she then cried out louder, ‘Oh my god!’

Fully inside her bum he now began fucking her, slowly building up his rhythm with each thrust.

I had to take a breath, as I realised I was subconsciously still holding it. Watching the vision before me as Martin began thrusting harder into Angela’s bum. I could see her legs trembling and her knees bending slightly as he held nothing back and used her ass to the hilt.

He still had both her hands held high above her head tightly and used his other hand to wrap around her tummy as he fucked her bum harder and deeper with each minute. Every so often he would suddenly without warning spank her bum hard with his free hand, then carry on fucking her. The sound of his bum slaps echoed loudly in the night.

This incredible scene went on for what seemed like an eternity but was probably half an hour or so. She just stood there, bucking back and forth as Martin fucked her ass furiously now. I could see her fingers flexing constantly and hear her gasps, and little grunts getting louder with each passing minute.

Also, I could clearly hear the sound of his thighs slapping hard into her as he pounded her ass relentlessly.

Martin then moved his free hand upwards and round towards her face. He then wrapped his hand firmly across her mouth which muffled her gasps as he reached his summit.

I am sure she was cumming then, but her gasps were overpowered by Martin’s own cries of pent-up eruption as he buried his cock as far inside her ass as he could while he came.

He cried out, ‘Oh, fuck! ‘ as he must have erupted his cum deep inside her used ass. He stayed buried inside her bum like that for a few minutes, then pulled out of her, and grabbed her by her hair, pulling her down to her knees. He then made her clean his cum-covered cock, straight from her own ass. Angela didn’t hesitate and spent a few minutes licking and sucking his still-hard cock clean for him.

This was almost too much to watch, my cock was now bursting through the front of my trousers as I watched her cleaning Martin’s glistening cock, straight from her ass.

Angela stood up, shakily on her high heels, suddenly she produced a loud bum fart, and I could just make out the tell-tale splatters of Martin’s spunk shooting from her used ass. Martin gave her ass one last hard slap, then he kissed her, pulled up his trousers then gathered up her skirt and top.

As they both descended into reverie together and began getting dressed, I quietly made my escape back around the cars and to the venue’s front door. I returned to our table, feeling hot, and sweaty and my mind was barrel-rolling like an out-of-control fighter plane! I sat and gulped my drink, trying to calm myself down so it wasn’t obvious I had been anywhere other than right here.

I waited for her to return.

After about five minutes I saw Martin walking back in and towards the bar, he looked like he had just stepped out for a moment. There was nothing to indicate what he had just done to Angela. Shortly after that, she returned, her hair looking out of place and windswept, her face devoid of lipstick, her outfit was back on, and though she walked a little unsteadily no one suspected anything more I am sure.

She walked over to me at our table smiling.

‘That was some cigarette’ I joked, ‘You have been gone ages.’

She looked at me like a cat that’s found the cream and said, We did a little more than smoke ciggies darling.’

She asked if we could go home, saying she was really tired.

‘Was he that good?’ I asked.

‘He was more than good babe,’ she replied.

‘I bet you wish you could have watched us?’ she asked.

I said, ‘Oh god yes, that would have been really something.’

During the cab ride home, she kept her legs firmly together this time, but secretly I knew exactly why!

After we got home she hurriedly went upstairs saying she needed a shower before bed. I noticed as I got up to our room that she had only put the top of the outfit in the wash bin. I looked down at her gold high heels, cast on the floor, and thought to myself, ‘If shoes could talk!’

Published 2 years ago

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