My daughter had been dating Tom for about four weeks. It seems Tom had recently suggested that the two of them do what most of the others in the district were doing and have a weekend away in a motel or resort either alone or with another couple. Jan liked him enough to agree to his suggestion but was concerned as she is a seventeen-year-old virgin and Tom is a few years older.
Tom, she informed me, has had sex with at least two other girls she is aware of. She wanted to go and was prepared to sleep with him, thus losing her virginity. She wanted my advice as we are remarkably close and have no secrets. We had previously discussed my loss of virginity as I had regretted the experience I had with her father.
She mentioned the possibility of STI and pregnancy as the sex education class had discussed this. She also mentioned many of her friends had begun using oral contraceptives, just in case, as she put it.
She asked me what I would suggest. I told her it was her decision; I would help and support her in making any decisions in that regard. I told her I would like her to enjoy her experience and not suffer as I did with my unfortunate experience. The matter of oral contraception was a good one and I suggested she begin using it to be prepared.
I am a young widower in my late thirties. Since my husband's death, I have taken advantage of a few opportunities to have an occasional casual affair during business trips but always with guys that are not employees of the company I represent. I have enjoyed one or sometimes two nights in their bed. I am aware some are married and ensure that they know and understand my rules. Jan is aware of my sexual experiences.
Jan, it seems, had made up her mind and that she was going to sleep with Tom. There was a tennis tournament in a couple of weeks, and they would be staying overnight at the tennis ranch in motel suites. Two girls would be sharing rooms and she had arranged with her girlfriend Sue, who was already sleeping with Jack, to swap rooms so each would be able to sleep with the guys in their rooms.
I told her she was so lucky to have a friend like Sue who understood.
I suggested Tom come around one night and we could discuss it if he would not be too embarrassed
Jan thought that would be a good idea for both of us. Jan and I could discuss it and afterwards and decide if I believed he was the right guy to start with. She said she was sure there would be others later, but she wanted her first to be memorable. She felt that if the three of us discussed it, it could be the night of her life.
Jan talked to Tom and he suggested the chat just be with himself and me. Had Jan been there, our discussion may have affected her decision as she listened to two experienced people discussing sex clinically or humorously. Tom did not want anything to be a concern to her, apart from being her first time.
Jan and I are extremely close and after the two of us discussed his proposition she believed that Tom and I alone would be the best way to discuss the ways for the two of them to get the best result possible.
The week before Tom and Jan were to have their weekend away, Tom agreed to talk about the planned weekend. He was not sure if it was a good idea but Jan had convinced him I was happy for them to enjoy their weekend together and wanted to ensure they were both aware of the consequences.
I had told Jan that I was happy she had chosen to use a motel rather than in a car for her first time.
I was more than happy to explain my situation to Tom and assure him I had no objections to him sleeping with Jan and that he was aware of the importance of it to Jan, and me.
…………
Jan arranged for Tom to come over to our home the night she had a tennis meeting to attend.
One of the first questions I asked of Tom, was if he knew she was a virgin, and this would be one of the biggest events in her life.
Tom told me he realised her situation. Jan had discussed it with him, and he explained all girls will tell you it is the first time. She was also aware that the two other girls he had sex with were anything but, and that was the reason he asked them. I asked him if he had ever had sex with a virgin girl before and he said he had not.
He mentioned he had heard stories from two guys that had ‘busted’ a virgin, as he put it, and the stories were both different. He said he wanted his experience with Jan to be more pleasurable.
I asked him to explain what he had heard and what he expected the experience to be like.
It was awkward for a few minutes. I then suggested he tell me about his two previous girlfriends.
I wanted to learn if he was aware that girls have orgasms? Did he last long enough for the girl to enjoy her experience with him? Did the girls say anything about his performance after it was over? Did he use a condom or what form of contraception did they use?
He was somewhat embarrassed to go into details with me. Gradually, I managed to get him talking. He thought I might be thinking he just wanted to have sex with Jan to achieve what his two friends had with their girls. Once he realised I only had Jan's well-being in mind, he opened up.
I then had to convince him I was not going to object to their relationship, I was more concerned that Jan’s experience would not be a disaster as mine had been. I admitted that at Jan's age I was having sex with boys and soon had a reputation, and I did not want Jan to get the same reputation. He seemed to relax a little. I was happy having learned Tom was twenty and mature. He was three years older than Jan, and somewhat experienced, having admitted he has had sex with two of Jan’s teammates. Jan already was aware he had fucked them, and they had enjoyed it.
After a short discussion, we both discussed the questions and it soon became obvious he knew girls had orgasms and both girls seemed happy with their experience with him. It had not been their first time and he had used a condom on each occasion as the girls were not using contraception.
Tom told me both girls agreed what they did was only for fun and they were not looking for a relationship with him. They had already fucked other guys. Their main consideration was they didn’t get pregnant.
He had later asked for another date with them, but both had said no. One of them told him she had a new boyfriend, the other the wrong time of the month, and asked wasn’t he dating Jan now?
Tom explained both had been back seat affairs in his car, and he admitted it was uncomfortable and was looking forward to being in a proper bed with Jan.
Both girls were friends of Jan’s, and she was well aware of his experiences with them.
After he had recounted his experience, he seemed far more relaxed and said I had not embarrassed him
I laughed and told him it sounded like a few of my experiences at their age. He relaxed and admitted he was looking forward to his first experience with Jan and honoured to be allowed to be her first lover.
He said she had initially rejected his request to have sex with him, but she had changed her mind after discussing it with me.
I questioned just how far they had gone together, and he admitted it was only hand play, neither had been completely naked together yet. He told me they had both engaged in some foreplay and masturbated each other. Jan had got him to ejaculate.
He also mentioned, one girl had volunteered to suck his cock rather than let him fuck her as she was concerned about pregnancy. Jan had not gone that far with him.
He then asked me straight out – was I really happy to let her have sex with him?
I said after our discussion, I could not be happier. I was sure Jan would enjoy her first fuck with him. She and I have agreed it will be exciting for her.
He then asked me about how I felt, knowing Jan knew I had sex with different men.
I told him it would have been a bit like his experiences with the two girls he had slept with. It was enjoyable and I had no feelings of guilt. Jan would never meet them.
The conversation became most relaxed and friendly and as I was sitting on the lounge next to him, I put my hand on his thigh. He then put his hand over mine and looked at me. and thanked me for being so understanding.
Our eyes met and there was something about the way we looked at each other. There was a distinct feeling of attraction, I got this strong desire to kiss him.
As he looked into my eyes, I shivered and I felt goosebumps, my nipples hardened, and I began to get wet. Our eyes never left each other which was rather erotic. The desire to kiss him was overwhelming. Suddenly the age difference faded.
I blushed a little as I had a fleeting thought of what he might be like in bed. I could not help myself, I asked what he would say if I suggested we go to my bedroom. Without waiting for his reply, I pulled him to his feet, took his hand and put it on my breast.
I squeezed his hand so he could feel the soft flesh of my breast. He realised what I was suggesting and began to resist. As he tried to remove his hand, I stopped him. He looked me directly in the eye.
He asked in a profoundly serious tone if I was serious. I replied by drawing him to me and kissing him. I wanted him so badly now.
He resisted for a few seconds. With my lips pressed to his, I slipped my tongue into his mouth and immediately felt him relax and begin to respond to my kiss and then our bodies embraced.
We continued to kiss and felt him adjust his position as I guessed his cock hardened in his pants. I was experienced enough to recognise his reluctance turn to acceptance. He said nothing but did not pull away.
I drew his body to mine, and he did not resist. I then kissed him again passionately pressing my groin into his and I could feel his hard cock and erect in his pants.
Without a word I took his hand and began to lead him to the spare bedroom.
He stopped and said that we should not be doing this. He was having second thoughts as I was Jan’s mum and it would be wrong for him to have sex with me. Fucking both mother and my daughter was wrong.
I assured him that what we were about to do was not wrong. It would be beautiful.
"Tom, you will enjoy this better than you have ever enjoyed anything in your life before," I was pleading with him. I would be devastated had he not gone on with it. I would have been shattered having taken him this far and not finished it. I was virtually out of control.
I assured him this would not impede him having sex with Jan. It would be an experience in his life that he would never forget or regret after he and I had fucked each other. He would probably not have the opportunity to fuck another woman as old as I am. It would be a milestone in his life. I assured him I desperately wanted him to fuck me.
He asked what Jan would say if she ever found out. I assured him she knew I fucked other men and he would be just another man.
I suggested that we keep it just between us. Jan and I do not have secrets, but this would be one I would be prepared to keep.
I could see he was not altogether happy about what I wanted. He resisted for a few seconds and then I believe my pleading was convincing him. "We will be good together. I am sure this was meant to happen. Please, please do not spoil it for me," I pleaded. "I promise you it will never come between Jan and you."
He took my hand and followed me into the bedroom. My heart was beating like a drum. I was terrified he may not have gone ahead with it. I let my dress slip to the ground and removed my bra in a swift movement and I stood bare-breasted before him.
As he slipped his underpants off, I slid my pants down to reveal my shaven vagina.
His hard circumcised cock stood erect in front of him. He was built like a man should be, his cock was thick and straight, longer than my late husband's. I was not going to be disappointed and I thought of Jan taking that into her for the first time. She would be more than satisfied.
I could see him looking at my bare vulva. He seemed fascinated seeing it bare. I doubt he had ever seen other girls shaved.
I asked if he liked it. He responded saying her had never seen a woman that had shaved her pussy.
Then he asked me if I was sure what we were doing was right. He was still concerned about fucking either an older woman or Jan’s mum, or both. I was not sure. I had to move quickly.
I held both his hands and looked into his eyes. I assured him it would be perfect and to have no fear. I wanted this to happen, he should not worry about it and to enjoy what we were about to do. Jan and I have shared many things and his cock would be one more thing. I said, "We have gone this far, please don’t let it stop now."
I told him I wanted to make sure that when he and Jan made love together, he knew how to treat her properly and gently, the first time. I knew he had fucked other girls, but I wanted to be sure he would satisfy Jan in the way a girl should be sexually satisfied.
I then put my hand on his cock and told him how wonderful it was. He was a real man in every way. "I will enjoy this as much if not more than Jan."
I stroked his cock a few times and then knelt before him taking his cock head into my mouth. I was so relieved when he accepted me and didn't try and retreat from me.
He stood still as he felt my lips and mouth cover his cock. I licked his pre-cum from the eye of it ran my tongue around the rim of it. I then felt his hands holding my head gently. He was enjoying the pleasure I was giving him. After a couple of minutes of sucking his cock, I took his cock out of my mouth and told him I did not want him cumming before he and I made love.
He said nothing. He was in awe of what was happening. I was not taking any risks.
I did not want to risk him being unable or unwilling to fuck me if I had got him to cum. I then went to the bed preparing myself for him to fuck me.
He followed, realising what was required of him. He had previous experience but fucking on a bed is different from in a car. He was going to have real sex in a real way with a real woman.
It seemed he had overcome his reluctance to fuck me and was now preparing himself for our experience. Tom asked me if it wanted anything different from a normal fuck.
I was curious. "What is a normal fuck?" I asked.
"Missionary," was his reply. I gather he had fucked the other girls in more ways than one.
"That sounds perfect for her first time," I told him.
I suddenly became Jan’s mum again.
I told him not to rush it. "Jan has decided to let you have the pleasure of her body and her virginity. She knows what she is doing but has no experience. She must be allowed to realise what it is that the two of you are doing and given time to recognise what you are doing with her. Once your cock is inside her there is no going back."
He was realising that fucking me would be different to fucking Jan. I was experienced and older, and Jan’s mum. It was me who was taking the initiative and directing him rather than him being in control and the dominant party.
He realised I knew what fucking was all about, it was not always to make babies. I was going to judge him. In other words, I was deciding if he was good enough to fuck Jan and get her virginity. Fucking me was no opportunity fuck, it was a test.
He was beginning to realise now that in fucking me, he was showing me that he knew what he was doing, and how to do it properly. He had to make sure Jan’s first fuck was something special. I would not be there to guide and correct him.
He would be fucking me, and he had to realise that in fucking Jan he had to make it feel special. He needed to tell her he loved her. Tom was now beginning to realise what I was trying to achieve.
My ambition was to make sure Jan’s experience would be one hundred per cent better than my first time. So many girls had no idea of how their first fuck would be remembered all their life and may affect their entire sex life. Some I knew as a teen, regretted their first experience because either it hurt them, or the guy had cum and just used her. He had no feelings for her or the fact it was her first time.
Pregnancy was also feared as many guys tried to convince a girl she could not fall pregnant the first time she had sex and would not use a condom.
Very few boys considered what a girl would feel like after her first time. They got what they wanted and that was the end of it.