Girl's Intro to Friend's Older BF

"I am fed up; sex has got to be better than what I am getting right now. I rarely orgasm and when I do it is not as good as when I masturbate. Is it the same for you Maddie?"

"Well, to be honest, the answer is no. I am loving the sex I am getting right now. Maybe you should try an older man like me. Mike is amazing, no one of my age has ever got close to being so good as Mike. He seems to know my body better than I do. I never know what we are going to do. He is totally in charge and I love it."

"Sounds great but I don't meet with older men who might be interesting or interested in me. How did you meet Mike and has he got any friends who would like to meet a frustrated young girl like me."

"Gail, there are lots of older men who would love to meet you, trust me. I wasn't suggesting all older men are great lovers, only that I have found one. You must meet him some time. I have told him lots about you."

"When, when can I meet him, he sounds fantastic. How often do you two get together?"

"I am due to be seeing him tonight at the pub. I can't wait, we have got the whole evening and night together."

"Can I come with you and meet him? He might even have a friend with him. Please can I come?"

"Funny you should ask. Last time he and I were together he asked me whether he was going to get to meet you. He seemed very keen to do so."

"What did you say?"

"I said, of course he could, as long as he promised not to fuck you."

"You didn't say that........ did you?"

"I most certainly did. However, it was a bit of a concern when he said that he was making no promises. I thought he was joking, but he just smiled at me and said 'it could be quite exciting, couldn't it?'"

"Are you still happy for me to meet Mike? I might want him to fuck me, and it might be quite exciting if he wasn't joking."

"I will ring him and see what he has to say about tonight. You must understand that I have never challenged Mike, on anything important, and I do not intend to start now. I cannot promise anything if you come with me tonight. If he agrees to you coming along it is completely up to you whether you accept the invitation. Do you understand?"

"You make it sound rather scary..... you make it sound very exciting. Please let me meet him tonight, I need some excitement in my life."

Mike was delighted to hear from Maddie that Gail was keen to come with her to meet him at the pub. Gail was excited about the prospect of meeting Maddie's older lover. Maddie was excited but apprehensive about her best friend meeting her lover.

Gail agreed to meet the couple in the pub before going home to change. She showered and spent much longer than usual selecting what clothes she wore. She tried different combinations on before settling for her favourite summer dress. It was short enough to threaten to give glimpses of her thongs, opaque enough to go braless, plunging enough at the front to tease and tight enough to show off her small but shapely figure. When she looked at herself in the mirror, she knew she looked sexy.

There was instant chemistry when Mike met Gail. Maddie spotted it immediately and although pleased how they bonded was slightly worried. She knew that if he decided that he wanted to get sexual with Gail, she would find it very difficult to deny him anything. She had never denied him anything, or wanted to.

Mike asked Gail about her recent boyfriend and sympathized when she complained about him. It was Maddie who explained to him that Gail's sex life was a major frustration for her. Mike listened and asked Gail what she had particularly enjoyed sexually in the past. It was a simple question but the young girl struggled to give any sort of answer. He prompted her asking whether she had enjoyed, giving or receiving oral, exhibitionism, voyeurism, bondage, spanking, anal play or role playing of any kind. This did nothing to help her give a cohesive answer as she was now embarrassed.

To try and help, Mike offered up that Maddie loved to be very submissive to his dominance. Maddie chipped in agreeing and adding that she loved to experience many things including anal play and bondage. Maddie perked up at this comment as she imagined her friend tied up having her bottom played with. It was Mike who then said,

"Would you like to try being submissive to Maddie and I for the evening? We could see whether you enjoy some of the things you quite clearly have not had the chance to try. Or would you rather we went back to my place and tied Maddie up and teased her until she offered to do anything we wanted if we allowed her to orgasm. I do so enjoy Maddie when she is desperate."

Gail looked at Maddie as if asking for help, or was it permission? Without saying anything Maddie made it clear that she would be happy with whatever her friend wanted. It took Mike to move things forward.

"You clearly need a little excitement in your life Gail. I am going to set you a small challenge that I am sure you will find at least a little bit exciting. I want you to go and sit on that barstool and chat up the barman. While you are talking to him, I want you to show at least some of the people in the bar what panties you are wearing. Please undo one more button on your dress to improve the view of your lovely boobs."

Gail's first reaction was surprise, quickly followed by questioning but then into excitement. Looking Mike straight in the face with an expression of both submission but also fight she undid two buttons. Her boobs were small but now the view of them plunged down so that they could be seen from the side. She was sure her nipples hardened as she did so.

The barman welcomed the attention of the attractive Gail, as he served the customers in front of her. The stool was tall with no arms which allowed her plenty of freedom of movement. She was able to swing her legs round casually giving anyone watching a view up her short dress. She became very aware of her thong, which now seemed to have worked its way between the lips of her pussy and the cheeks of her bottom.

She loved flirting with the barman, something she would not have considered doing normally. She became very aware of her body. The barman was clearly enjoying the view he had and she wanted to ensure that she showed more than a few of the people in the bar her thong. Mike and Maddie watched on with amusement as it became clear that Gail was thoroughly enjoying her bit of exhibitionism.

Plenty of people in the bar noticed Gail, and in particular noticed the flashes of thong that she offered. For one person this display was too much to ignore. Brenda had watched Gail since she entered the bar and had loved what she had seen. She couldn't resist approaching Gail and shocking the young woman by saying,

"I love the view, you have been offering the world, of your red thong, but would love even more to remove it and kiss your pussy. If you would like to experience my tongue on your clit please follow me into the ladies."

Gail was shocked to the core by this outrageously blunt approach by an attractive older woman. She couldn't think how to reply before Brenda smiled and swept away to the ladies. The barman gave Gail a knowing look and put the third of Gail's drinks on the counter. When Gail had paid, she returned to Maddie and Mike feeling confused but buzzing at the same time. Maddie immediately asked what the woman at the bar had said to Gail. When she heard the answer she laughed and said,

"Please don't let us stop you. You wanted something different sexually and you have been offered it. Maybe you would enjoy a woman's head between your legs. Friends of mine have said that no man can give oral as well as another woman. I of course said that they had obviously not been with you Mike."

"I am sure I would much prefer Mike licking my pussy more than any woman. I think I will give her exciting offer a miss for tonight."

With all three now laughing, it was Maddie who teased,

"Well that is all sorted then, back to your place Mike and you need to show Gail just how skilled you are. If you fall short of expectation then I will have to see whether I can prove my friends right."

Maddie had been joking but none of the three could quite dismiss the idea from their minds as they drank their drinks quietly. When their drinks were finished it was Mike who enquired,

"Are you coming back to mine with us Gail?"

Gail realised that if she accepted, she was accepting much more than having a drink or a chat. That was okay because she wanted so much more than to talk and drink. Mike did serve up drinks when they were sitting in his lounge. He sat the two girls down next to each other on the sofa and sat opposite them in an arm chair.

"So Gail are you really interested in older men, or are you just teasing Maddie and me?"

"All I know is that what I am getting right now is just not enough. I would be delighted to try some different things and being with an older man would certainly be a start."

"Would being with you best friend and her older man be different enough? If so, if you feel like being an exhibitionist and a submissive, I might well be able to help you, right now. No probs if not."

Gail knew that there was no way she was going to say no to almost anything. She had been instantly attracted to her friend's boyfriend and Maddie had done nothing to suggest that that would cause a problem. In fact, Mike had talked to Maddie and she had not only been happy to agree to Gail joining the two of them, but had been enthusiastic and excited by the prospect. Gail didn't give a verbal reply but there was no doubt left in any of the three of them that she was in.

"Both of you open your legs. You will both masturbate with your panties on. You are to show me your arousal, but you are not to orgasm. I will see whose display is most exciting and who I therefore choose to fuck."

Neither girl hesitated and Gail particularly saw the competitive aspect as a challenge. Her levels of arousal had enjoyed peaks and troughs during the evening and it took little playing with her clit for her to reach a point where it would have taken very little to send her into an orgasm. Maddie was delighted to build her excitement slowly but was soon not far behind her friend.

"I want you each to tell me when you are right on the edge. Once you are both there it will be interesting to see which of you can climax quickest. Don't even think about cumming without my permission."

Maddie had enjoyed these sort of challenges before with Mike and loved them. Gail had never experienced anything like this with a partner and edging like this while masturbating had never felt this good.

"Fuck, I am so close please let me cum, so close....... Pleeaasse."

"Ok, you both look nicely warmed up. Please strip completely naked and resume masturbating. There is just one little difference and that is you are not to touch your clit whilst doing so."

"But you promised, you promised that we could race to climax. I was so close, so fucking close."

"I said, it would be interesting to see which of you would orgasm quickest. That is only one of many interesting possibilities for this evening. Right now I want you both naked. I will ignore your outburst just then, but that will be your last. There are many ways to punish young ladies. Some of them can also be pleasurable, but if you step out of line again you will not enjoy the punishment. Do I make myself clear Gail?"

Gail bowed her head and muttered, "yes sir."

Maddie smiled to herself realising that her friend was beginning to understand the situation. She hoped that she would not only understand the submissiveness but grow to love it. Both girls were quickly naked with minimal fuss. Maddie used both of her hands to play with her boobs and in particular her nipples. Her full boobs were capped off by thick, long nipples that instantly incorporated the surrounding areola. The contrast with Gail's was dramatic. Her boobs were smaller but were almost covered by huge areola surrounding small sensitive nipples.

Gail thought that Maddie was reaching for her clit with one hand and was waiting for Mike to rebuke her about it. Instead Maddie's hand reached further between her legs and found the crinkled skin of her anus. She worked a nipple with one hand and teased her sphincter with the other. Gail was working both of her nipples but this was not getting close to the levels of her previous arousal. She was a little shocked when Maddie moistened a finger before pushing it deep into her bottom. While Gail had enjoyed limited anal play she was shocked by her friend's lewd display, but was unable to ignore it. It was Mike who asked,

"You look rather disturbed my dear. Do you not enjoy anal play?"

"I, well I, I don't know I suppose I have never really done much. Once or twice I have enjoyed it being touched during my orgasm, but that is about all."

"Maddie be a good girl and show Gail how pleasurable a finger can be if introduced into a willing bottom. Just lie back and enjoy your beautiful breasts as Maddie tests that lovely tight bottom of yours."

Maddie knelt between her friend's legs and using just her middle finger teased her tight anus. It took many seconds before Gail relaxed and Maddie slipped her lubricated finger a couple of inches inside the warm orifice. She didn't push further until Gail relaxed again. Now Maddie pushed in deep and explored the area with the pad of her finger. It was Gail moving her hips that started her bottom being fucked by the single digit.

The young girl was stunned by how wonderful it felt and how her hips took on a life of their own, as they ensured that the finger reached new depths and travelled in and out of the previous virgin territory.

This lasted less than a minute before one of Gail's hands left her excited nipple and plunged between her legs. The instant her fingers found her clit her body exploded in a shattering climax. She screamed her excitement; she screamed her denial and then she screamed her apologies. Maddie's finger became demanding as Gail roared her way through the most violent climax she had ever experienced.

Mike let the exhausted girl settle before saying,

"Well what do I do with a girl who orgasms without permission. I will have to think what the correct punishment is. Do you remember how I punished you when you climaxed without permission the first time Maddie?"

"Yes, you wouldn't let me cum again for two whole, long weeks. That should have been punishment enough, but you brought me to the brink of orgasm every day during that time. I nearly lost my mind, but I have learned not to disobey you since."

"I think today, I will show young Gail some understanding. Go and get your pink butt-plug and ensure that her bowels don't get too much of a rest."

Maddie lubricated the butt-plug before taking her time burying it into her friend's bottom. It stretched the tight orifice but once it was settled in place Gail felt wonderfully full.

Mike now stripped and offered Gail his erection as she knelt in front of him. She played with his balls with her hands and used her lips and tongue to tease the large purple head of his cock. When he was ready, he sat on the chair and invited Maddie to come and sit on his lap, facing her friend. His erection sunk easily into her aroused pussy. When he reached round her and found her clit her moan was one of pure pleasure.

There was no urgency as he fucked her gently and teased her clit with skilled fingers. She was practically purring as her clit responded by growing thick and long enough for him to trap it between his finger and thumb.

"Oh, Daddy may I please cum, you feel so wonderful?"

"You can cum whenever you want, but I will carry on fucking you until I am good and ready to flood you pussy with my juices."

"Thank you, Daddy, thank you. I am going to cum so haaaarrrrddd."

She fell silent as her body convulsed time and time again, holding her breath as it did so. Mike kept playing with her clit even as her body started to settle. She complained that she was too sensitive but this only led to him being even firmer. Her orgasm that had died seconds earlier re-ignited hitting her with two peaks of painful pleasure, before she slumped back against him.

"Gail get on your back on the floor. Maddie is going to show you just how good she is at licking pussy. No leave the plug exactly where it is."

He positioned Maddie so that he could enter her from behind and watch Gail as her friend latched onto her clit with her mouth. The view he had was wonderful and he was in no hurry to orgasm and give it up. Gail was not really in control of how quickly her excitement grew as she held her friends head until she exploded in pleasure. As she felt her friend climaxing, Maddie's arousals increased and sensing this Mike buried his thumb in the anus in front of him. Maddie found her clit with her fingers and her orgasm milked his cock until he emptied his balls deep inside her.

Gail thought that watching her friend orgasm was the end of the sex for the evening. Mike reminded her that she had not been punished for having her first orgasm without permission. He said she could choose her punishment. Her first option, was to receive a dozen from the cane on her bottom, her second option was for him to play with her supersensitive clit. To help her decide he used his fingers to rub her swollen pussy and test her clit. Gail's clit transmitted only pain to her brain but she was sure that the cane would be far worse.

She was soon sat, with her back to her friend who was sat at the top of the bed. Maddie's legs were hooked inside Gail's holding them invitingly wide apart for Mike. Initially Mike left the butt plug where it was and brought his mouth directly to Gail's clit. He was not gentle with it, but this in many ways felt better than when he allowed his tongue to gently tease it. Maddie used both her hands to find her friend's breasts and tease her sensitive nipples. Gail pleaded with Mike to leave her clit alone as it was far too sensitive. He offered to use the cane on her clit if she would prefer it.

Gail wondered what Mike had in mind when he removed the butt plug. She thought he might replace it with his cock. She would not have fought him if this was what he intended. Her clit felt huge and raw sending only painful messages to her brain and she pleaded with him to stop touching it. She thought he was responding to her pleas as he temporarily gave her some relief as he inserted two fingers deep into her bottom. She was stunned how wonderful they felt, particularly when he curled them upwards and fucked her with them. When his mouth found her clit again the pain was just as bad, but along with it was arousal. Gail felt the two sensations battling to dominate her helpless body.

"Would you like me to stop punishing your naughty clit, or do you want to experience more?"

A minute earlier, she had wanted nothing more than the pain in her clit to stop, now she was totally confused. The pain was there but the arousal was strong and demanding. This was not how sex should be, not like sex had ever been but something in her didn't want it to end.

"Please don't stop, it hurts but it hurts in the most wonderful way. Punish my clit, my nipples and my arse."

There was no gradual build up to her orgasm like she always experienced. As the last words left her mouth the pain exploded in her head, the pleasure exploded in her head, the climax exploded in her head. Both Mike and Maddie worked her body with no hint of subtleness right through her violent orgasm that both frightened and excited her in equal measure. It disappeared as quickly as it struck and Gail curled up in a ball totally exhausted. She dozed to the sounds of Maddie and Mike making love before falling into a deep sleep.

Over the next months, Maddie was delighted to invite Gail to join her and Mike. Mike was delighted to welcome Gail into their bed, but most of all Gail was delighted to experience sex the likes of which she had never even dreamt of. He might have been the first older man in Gail's life but he would certainly not be the last.