Friends Lose Their Virginity

"Can I talk to you about Jan? It is a really difficult thing to talk about but as her best friend I wanted to talk to you as her father."

"I hope you know that you can talk to me about anything Sandy. What is bothering you?"

"I am nervous and not sure how to raise this so I will just say what I am thinking. We are both off to uni at the end of the summer and we agreed that we did not want to go off as virgins. Jan knows her relationship with her boyfriend will finish before she goes off to uni. She does not want to complicate the breakup by having sex with him. She also wants to loss her virginity to someone with experience without any long-term commitment."

"You are right it is very difficult to talk about. I know you are both eighteen but she is still my little girl and although I know that she is bound to be physically involved with her boyfriend I have not yet really faced reality. There is logic to what you have said even if it does seem a little calculated. I am also not sure that finding someone who would be suitable would be easy."

"Well that is where I think you could help."

"What do you mean I could help?"

"Please count to ten before you say anything about my suggestion. There is only one person we have identified as possibly fitting the bill. That person is your best friend, my Dad."

It took every ounce of his self-control not to explode at the thought. In the five seconds before he said anything he had calmed down quite a bit.

"Your Dad? Your Dad sees Jan just like a daughter in just the same way I see you like a daughter. There is no way he would consider anything of a sexual nature with Jan."

"I knew you would say that and I respect that. You said yourself that there was some logic in the idea of Jan losing her virginity to an experienced man who cares for her but would not want to get romantically involved with her. Can you think of anyone who would be more suitable?"

"I didn't suggest that it was a good idea for Jan to sleep with an experienced older man only that I could see some logic. Bob is a good friend but I think that would make it even harder for me to even think about talking to him about it. It would be the strangest thing thinking of him making love to Jan."

"Thank you for not hitting the roof at my suggestion. You do seem to have at least got to the point of considering it."

"I am not sure what Jan would think about your Dad making love to her. He is obviously old enough to be her father."

"Trust me Mr. Booth let's just say Jan would not be upset by the possibility."

"How would you know what she would feel about?"

"How can I put this in a suitable way? Let's just say Jan has always found him very attractive and when we have discussed this possibility she has become very excited by it."

"You mean you have discussed your Dad making love to Jan with her?"

"Oh yes I would not be here talking to you like this if we had not discussed it in great detail. She asked me to ask you to ask my dad if he would be kind enough to do this for her. How could I possibly refuse?"

"Now I am really shocked. I thought we were just talking about a theoretical situation but now I realize it is something much more. What do you feel about your best friend making love to your Dad."

"I think it is really neat. I love my Dad and since Mum died,......... well enough said. I love Jan and I know it is something that she is desperate to happen. I know it is kind of strange but I think it would be lovely too."

"It is more than strange it would be the same as me making love to you. Oh sorry I should never have said that please don't be upset with me. I could never think of you in that way."

"You are right it is exactly like you making love to me. Right now Jan is probably having exactly the same conversation with my Dad about you and me. Now it is my turn to apologize. I did not want this raised in this way. I wanted my dad and you to talk about things. It is complex but Jan and I would love this all to happen. It would bring the four of us very close. I completely understand if you do not find me attractive as I know that would be necessary."

"Sandy although I have never thought of you in that way I can promise you that you are the most stunning girl I have ever seen. If anyone says otherwise they are a liar. The whole situation is huge and I cannot take it all in. I am due to have a drink with Bob tomorrow. If Jan has had the conversation about us by then I will at least raise it with him. That is absolutely all I am committing to."

When they met for the drink Bob was as stunned by the suggestions made as Pete had been. Their first reaction together was that it could not happen. Bob asked Pete what he thought would happen if they refused to go along with the requests. After much thought Pete said

"Knowing my daughter if she has decided to loss her virginity before going to college she will do so. She has clearly decided her boyfriend is not man enough for the job. I am a little worried she will do something silly. In the context of this thinking the idea of you sleeping with her doesn't sound so bad. I feel a bit like a pedophile even thinking about Sandy in a sexual way. She is a lovely girl but like a daughter certainly not a lover to me."

"I love my daughter to bits but I had assumed that she had been sleeping with her last two boyfriends. The idea of her rushing into selecting someone to take her cherry is really disturbing. We seem to be coming to the conclusion that their idea really does have some merit. Could you live with the idea of me sleeping with Jan?"

Both men had a couple of drinks more than usual and before they left to walk home from the pub they had agreed to consider the proposition. Both of them knew that the idea of sleeping with the girls was completely ridiculous but both also found it disturbingly intriguing and if they were really honest exciting.

The girls had also had a meeting at the same time. Their discussion was excited, as they were certain that they could persuade their fathers that it was the only solution to their problem. The discussions were about how to set it up and how good they thought the sex would be. They agreed that they wanted to be wined and dined and spend the night at a nice hotel.

It was a week later that each of the fathers picked up their date for the evening from their friends houses. The men had suggested a double date in a posh hotel but the girls had said that they didn't want their dad's anywhere near them on their special night.

When Bob picked Jan up from Pete's house he was shocked by her appearance. She was beautifully made up and she was dressed with sophistication but eye-popping sexuality. She looked far older than her years with a maturity that was comforting.

"You have taken my breath away. You're looking frighteningly beautiful. I have to ask you are you sure you want this?"

"I want this more than I have ever wanted anything in my life Uncle Bob."

"If you call me that one more time I will walk away from you straight away."

"Sorry Bob it was a bit of a tease. The answer is still yes please."

The hotel restaurant was quality and unlike anything Jan had experienced before. Bob was initially nervous that he would look like a pedophile but Jan behaved with such sophistication that the young attractive waiter soon realized he was wasting his time. Jan had made it very clear that this was not her father but a partner who she found very attractive.

It was strange but both of them grew in confidence as the meal progressed. They talked about Jan's expectations of University life. Bob said Jan should look to live the University life to its fullest. Yes work hard but don't miss out on the social or sporting aspects. Jan asked Bob about his romantic life after his wife had died. He admitted it was as good as non-existent. Jan asked him whether he had used Internet dating and when he said no her reply was.

"You are an incredibly attractive man. You are also incredibly illegible. You have given your life to Sandy but she will soon be off to Uni. It is your time make sure you use it."

This comment almost reduced Bob to tears but he realized it showed maturity beyond her years. For the first time he could imagine making love to this stunning female as an equal not as the daughter of his best friend. At the end of the meal he ordered coffee to be taken in the lounge.

Their enthusiasm to retire to the bedroom was mutual but they both loved the anticipation that had been building all evening. Their coffee and chocolates were taken with an excitement that was for the first time in the evening purely sexual.

When they eventually closed the door of their room Jan was hit by an excited panic. Suddenly it was all very real and she became scared as well as aroused. Part of her wanted to rip his clothes off and devour him. He sensed her confusion and took her into his arms. This calmed her significantly.

"You don't have to do anything that you don't want to. I would be very happy if you would like just to curl up together and I could cuddle you until you fall asleep. You are free to say whatever you want to Sandy or anyone else, I will not contradict you."

"Would you really do that if I asked you to? You are amazing. There is nothing I want more right now than you to make love to me but it is nice to know that there is no pressure."

He suggested that they took just their shoes off and lay on the huge bed before starting to undress each other. They took their time taking turns to take a garment off the other one. There was no rush and it was many minutes before they were left in only their underwear. His were a pair of jockey shorts that were not doing a good job at hiding his erection. Hers were a matching set of opaque bra and panties. She was delighted that even when covered she was sure he was bigger than her boyfriend who she had only seen naked on a few occasions.

It was his turn to remove an item of her clothing and he was slightly nervous. In fact he had no need to be as she was very keen to show off her breasts that she knew were so admired by both her male and female friends. She was amused at how he managed to unbutton her bra without the usual battle her boyfriend always encountered. He caressed using his palms to cover the whole area of her compact and firm breasts. She loved the way his palms excited her nipples without concentrating on them, as it was arousing in a gentle sensual undemanding way.

"My turn now. I cannot wait to see your cock."

His erection caught on the waistband of his jockey shorts as she nervously took his last garment off. She was delighted at the sight of his erection. It was bigger than her boyfriends with a large head that was already dark reddish purple. In reality Bob was only a little more than average size but to her his cock felt excitingly big. She explored it with her hands fascinated that it was so hard and yet silky at the same time. He was amused that her touch was so light particularly when she played with his balls.

Her boyfriend had always pleaded with her to take him in her mouth, something she always refused. She was so keen to appear mature and sexually relaxed she looked up into his eyes as she took the smooth head into her small mouth. He smiled inwardly wondering (wrongly) whether she really was as innocent as she made out. Innocent or not her mouth felt beautiful as she played gently with just the large excited head.

"Please Bob will you fu....., make love to me now?"

"I will make love to you when you are fully ready. Now just lay back and enjoy it as I help you get fully ready."

She went to protest that she was more ready than she had ever been but decided to just let him take charge. He laid her on her back and took hold of her panties with both hands. She raised her hips immediately to ease their passage and opened her legs after he slipped them off her feet. The warm sensual aroma that filled his nostrils confirmed to him just how excited she already was. Her dark nipples stood proud on her pale boobs that had not changed shape as she had lain down. Her stomach was flat but toned and her legs showed that she had clearly kept playing active sports. A small triangle of hair decorated just above and seemed to point to her pussy. Bob couldn't imagine a more perfect body. Her legs were far enough apart for him to find her pussy with his mouth and tongue.

She bent her legs and let them fall further apart to give him fuller access. Bob was amazed at just how neat, tight and small her pussy looked. He could see that her natural lubrication had pooled at the base of her swollen pussy even though her lips were barely open. They did open slightly at the top where he hoped to see her clit. As aroused as she was there was no sign of it. He eased the lips apart with his fingers and brought his mouth to where the hood was hidden. Her small clit soon pushed through the hood and Jan inhaled and held her breath as the sensations threatened to overwhelm her. When she did release her breath she gasped

"Fuck that is amazing."

He had never heard her swear before and it took him by surprise. The aroma and taste of her natural lubrication was intoxicating to the older man. He reflected to himself that even if he did not penetrate her tight pussy he would remember these moments for as long as he lived. As for Jan she couldn't believe that any sex could be this good. She had never had an orgasm with her boyfriend and although she enjoyed masturbating to orgasm this was completely different. He was just able to reach up and find both her nipples with his hands as she dropped her head back against the pillow with a deep sigh. She was desperate for penetration but even the promise of this was not enough for her to want what was happening to her to stop. As he sucked her expanding clit he was able to use his tongue to further excite it.

As wonderful as it felt eventually she pleaded with him to fuck her. He ignored it the first time but when she begged him the second time he found her nipples with his fingers and thumbs while increasing the pressure on her clit. She wailed as she realized that she was going to orgasm on his mouth not on his prick as she had always hoped. She had no time to protest as her whole body exploded with such force that he had to abandon her nipples to hold her still enough to keep in contact with her clit. The sight of her beautiful face becoming consumed by her climax was so arousing he was concerned he might orgasm himself. Finally her body relaxed between the occasional spasms that shook her body. There was a look of disappointment on her face that he didn't understand until she said,

"I wanted to orgasm with my first prick inside me why did you let me cum like that?"

"What is the rush, we have all night? I wanted you to be completely relaxed and ready to take your first prick. Your orgasm will relax you and hopefully make the experience even better. Now would you like to rest before we make love?"

"No I want to feel that cock of yours where I have been fantasizing it being for days."

Bob now loaded his fingers up with lubrication from a bottle. Unnecessarily he added it all around her pussy and up to her clit. He only just penetrated her pussy in spreading it inside her. Thinking it could be a real passion killer he turned away as he put on a condom and covered this in the same lube. Much to her surprise he laid on his back and beckoned Jan to kneel over him.

"This way you control the entry so that it is not painful for you."

Jan did not expect much pain as she had been using firstly a hairbrush and more recently a dildo during masturbation sessions. She was happy for him to believe that she was a virgin in every sense of the word. She knew that he was much bigger than anything that she had used and that she would be stretched like never before. She wanted to be stretched like never before. She took no time placing his prick at the entrance to her tight pussy. She looked into his excited eyes as she eased herself down onto his prick. For a second his erection, as hard as it was, threatened to bend until it found the correct angle and it eased a couple of inches into her welcoming but tight pussy. She held her breath expecting some pain but felt none only the pressure of being stretched. Suddenly the tension that had been building in her body disappeared and she exhaled very slowly.

"My god that feels good."

He smiled as firstly she lifted herself up before easing another couple of inches of him inside her. She felt so tight to him he was not sure it would be comfortable for either of them if he fully penetrated her. She had no such concerns and slowly increased the length of her thrusting down on him as the lubrication and the angle allowed. The heat and the tightness took him by surprise and he fleetingly thought that he might embarrass himself and disappoint his young lover.

Finally Jan was able to settle her weight on top of him as she was fully impaled on his cock. She was delighted to realize that she had been able to take the whole of what she had convinced herself was a monster cock without any pain. She looked down at Bob with a look of triumph and expectation. He couldn't resist just pushing himself up into tight pussy to see her reaction. Bob was delighted to see this was greeted by a huge smile. They were both a little cautious as they found a rhythm and depth that felt good for them. Jan loved the feelings but was sure that she would not orgasm a second time. She felt incredibly close to her friend's father and wanted to make this special for both of them.

"Can I kiss you, please?"

Bob found this question both lovely but also funny. They were both laughing as she lent forward and rubbed her lips over his. It felt so right for her and so different from the aggressive kissing that her boyfriend always offered. Bob loved the sensuality of this simple act. He brought his hands down to the side of her face and without thinking about it took her earlobes between his fingers and thumbs. Immediately Jan's gentle thrusting became far more urgent. Bob stopped playing with her ears until she told him that it was like having her clit or nipples played with. As his playing with her earlobes recommenced her thrusting went from firm to urgent. She tried to grind down on him to increase the pressure on her clit. She knew that everything felt great but it was Bob who realized first that she might well be building to another orgasm with surprising speed. He wanted to take hold of her beautiful bottom with his hands to give him extra control but decided that her ears were more important to her right now.

Jan was setting the pace until Bob sensed the time was right and bending his knees changed both the angle and the amount of purchase he could apply. He knew it was right as Jan let out a wail and let him take over. She knew now she could enjoy another orgasm if he kept their new rhythm going long enough. As for Bob he wanted nothing more than to see her loss all control as he fucked her firmly.

They both got their wish as they seemed to find that a certain rhythm and depth had her struggling for breath. Having found this her climax arrived with such speed he was able to hold his off as she exploded both verbally and sexually. She screamed praise at him, thanked him and frightened herself by promising everlasting love. When she did finally regain control of what she was saying she laughed off the reference to loving him while telling him that she had never enjoyed an orgasm so much. She was surprised when she noticed that he was still rock-hard. She had thought that he had cum while she did. Now she wanted to see him cum and she knew exactly how she wanted it to happen.

An image that usually paid a part in her recent masturbation was the image of her parents making love. She had come home early from some school event a couple of months earlier and had stood watching them make love passionately. They had both been kneeling and her father was holding her Mum's hips from behind and fucking her vigorously. Her Mum's exclamations made it quite clear that she was loving it.