Dear Diary by allinmyhead (Story)
This is a diary style story I had written about me by a fetlife friend.
Dear Diary,
My daughter’s boyfriend is so sweet. He is so devoted to her. Always doing nice things. I love watching them together, they are such a cute couple. I must admit to being a little worried though. Hard as it is to believe in this day and age, they are both virgins. They’re old enough to drink and haven’t had sex yet. I’m proud of them, but I don’t want my daughter’s experience to be ruined because Ricky doesn’t know what he’s doing. I’ve decided that I’m going to teach Ricky how to do it and maybe coach him through his first session with Diana. I’m just undecided on hands-on his instruction should be. I think I’ll speak with Diana and see how she feels about it. After all it is her virginity. LOL
Dear Diary,
So I spoke to Diana about her and Ricky’s relationship, about how close she thought they were to having sex, what questions she might have about the actual act, etc., etc. She was a little embarrassed, but the fact that I’ve always been open and honest with her in all our discussions helped her be the same. She is a little afraid of it hurting, but she is more scared of doing something wrong. After we discussed everything that could happen, and the fact that there wasn’t much she could do wrong during the actual PIV portion, we got out my dildo and I showed her some hand- and blow-job techniques. I have to say the girl’s a natural. Takes after her mother. I’m so proud. I also showed her how to put on a condom and impressed its importance on her, even for their first time with anyone. Start with good habits, stay with them, I always say.
Dear Diary,
Diana came to me today and said she had spoken to Ricky and that they would like me to teach him, but that they wanted to keep his virginity for her. I have to admit, Diary, that the thought of initiating that cute, young man into the ranks of the actively sexual is very arousing. All that smooth, muscled flesh and the innocence. Yummy. Just the thought makes me need my vibrator.
Dear Diary,
I spoke with Ricky today. He is quite eager to begin his lessons. I asked him what he had done so far. Can you believe all he has ever done is kissed a girl? Hasn’t even fondled a boob. Not even through a top. Amazing! I made him kiss me, just to see how well he does that. He was rather stiff at first. I guess kissing your girlfriend’s mother is hard to deal with. He’s not fooling me though, I saw his erection. He did relax when I reminded him that Diana had agreed to this. He wasn’t bad, a little mainstream. I showed him some tricks. I had to pretend not to notice when he ejaculated in his pants. I didn’t want to embarrass a very promising pupil, but I must say I really enjoyed the sense of power I got. Diana came to me later and thanked me. I guess he went to her to “practice”. LOL
Dear Diary,
Today I showed Ricky how to feel up a woman and make it seductive. I told him to kiss me and while we were doing that, I took his hands and had him feel my breasts and my ass. By the way, I must say his “practice” with Diana paid off. He’s a much better kisser. I actually got wet. I had him slide his hand under my top and slip it inside my bra. I soon had him thumbing nipples, rolling and pinching them and squeezing breasts like a pro. I even had a mini orgasm when he kissed and licked my neck. Such a fast learner. Diana also seems to be very pleased. She keeps thanking me.
Dear Diary,
Today we have progressed to taking off shirts and actually dealing with naked skin. Oh my, I haven’t felt muscles like those in years. It started out well but then youthful enthusiasm got the best of him and it turned into a bit of a mauling. I’m afraid I got very stern with Ricky and even spanked him a bit. I must tell Diana that he really seemed to enjoy that. I extended our session today until Ricky was able to treat breasts with the respect and reverence they deserve. Once he calmed down he was able to transfer his new kissing skills to my breasts. Quite divine.
P.S. I think he may need to throw out his underwear, he came many times. Ah, youth and its recovery time.
Dear Diary,
Ricky is progressing quite nicely. Today’s session reviewed all he had learned so far and added fingering the pussy with pants on. I had him stand behind me, while we stood in front of the mirror. I showed him how he could hit the erogenous zones of the neck and ears, fondle the breasts and play with the pussy all at once. I had him slide his hand down the front of my pants and tease my clit through my panties. I told him when the panties got soaked it was time to go flesh to flesh. It didn’t take long. While his fingers explored I explained to him what he was feeling and the different things he could do. I let him play as long as he wanted and rewarded his efforts with a massive orgasm. You should have seen the astonishment on his face when he realized I had cum. He was so proud of himself. Definitely got an A from the teacher.
Dear Diary,
Diana came to me this morning wondering what was wrong with her. It seems Ricky showed her his lesson and she didn’t cum. I explained to her that sometimes it takes a while for young women to have orgasms. That some people have an easier time than others. I said it would happen eventually as long as she didn’t stress over it. I asked her if she enjoyed it. She said she did for a while but then it got painful. I said that comes from trying to force it. She was so upset about her perceived deficiency, that I finally had to prove to her that she was capable of cumming. I had no idea my girl wasn’t even masturbating. I got out the lube and Hitachi and talked her through it. It took some time for her to find the placement and setting that worked for her, but when she finally did, she had such a spectacular orgasm, she spent the next hour in a daze. She was so beautiful, Diary, watching her was so arousing. If she hadn’t been my daughter I would have had to have tasted her and helped her out. As it was I had to go to my room and put my toys to good use. Does that make me a bad mother? I did warn her to not expect the same reaction with Ricky and to not rely too much on vibrators as they could make her less sensitive. The fact that she proved to herself that she could have an orgasm cheered her immensely.
Dear Diary,
It seems today is about reassuring young people. Ricky was also upset about Diana not orgasming. He thought he had done something wrong. After repeating my explanations, I had him show me what he had done. I even held back for a while to see if he changed his tactics when he got impatient. He was able to pull an orgasm from me even with me holding back. I told him not to worry, that he was doing fine. I let him practice everything for as long as he wanted. I must say I find teaching greatly rewarding.
Dear Diary,
We took a big step today. I taught Ricky how to pleasure a woman orally AND how to control himself a little bit so that he didn’t cum as soon as he was touched. After explaining how each woman was different, both in what her pussy looked like and what she reacted to, I stripped and lay on the bed. I had Ricky get up close and personal and explained what he was looking at. I had him get me off with his fingers so that he could see the changes my body went through. He was quite impressed with my clit’s ability to play hide and seek in its hood. Once he was comfortable, I had him lick me. We experimented for hours. Tonguing, sucking, nibbling, with fingers, without. I made him do everything I could think of. I showed him how to tell the difference between a “that doesn’t feel good” wince and an “Oh yes! Do that again” tremor. I lost count of my orgasms. Once I felt he was fairly confident I had him take off his clothes and I played with his cock. Diana will be pleased, he has an impressive package. He came as soon as I grasped his cock. I told him that would never do. Thanks to his quick recovery time we were able to work on his stamina. Although every time I added something new, we had to start over. I loved filling my mouth with his heavy cock and the reaction I got when I sucked his balls was delightful. We finished the session with a satisfactory 69 with me on top. Mmmm, yes, quite satisfactory.
Dear Diary,
Today was my last session with Ricky. I’m a little sad, but I’m pleased with his progress. He will make sure my little girl enjoys herself as much as possible for a first time. I made him keep his underwear on so that we wouldn’t inadvertently slip up, or in as the case may be. ;-P I showed him all the different positions and what benefits he could derive from them. I really wished that Diana didn’t want his virginity for herself, but promises are promises. Then we had a long talk about what he might expect from Diana. I told preparation and going slow would be paramount for her comfort and how he could distract her at the moment of penetration so that it didn’t hurt too badly and the pleasure outweighed the pain. Then I gave him a final kiss and left him to it.
Dear Diary,
Diana and Ricky came to me today and asked me to be with them during their first session. They wanted to make sure they did everything correctly. I tried to decline, I really did, but they were adamant. So I sat in a chair next to the bed and watched them come together for the first time. I tell you Diary, it was all I could do to keep my hands to myself. Watching those two beautiful young bodies experience sex and all its wonders was so beautiful. And the connection and love they shared brought me to tears. Ricky did me proud. He went slowly, just kissing her for a long time before removing her top and nuzzling her breasts. He soon had her moaning and begging for more. And when he took off her pants and knelt between her legs, I thought I was going to cum just watching him make love to her pussy with his mouth. She actually orgasmed and it was so touching how he just held her afterward. Then he removed his clothes and I saw a glimmer of fear in her eyes as she saw how big he was. I’m sure she was wondering how it would fit. She grabbed my hand and I reassured her that it would be okay. I made Ricky lie down and took Diana’s hand and stroked Ricky’s dick with it. I had her kneel over him and told Ricky to play with her clit. When she was writhing and moaning again, I placed Ricky’s cock at the entrance and pushed her down while Ricky pushed up. I made him stop and wait, still playing with her clit, until she moved on her own. Then Ricky started moving slowly and I left them to their beautiful passion.
Dear Diary,
Diana came to me today. She hugged me and told me what a wonderful experience she had. “Amazing” was her word. She said I helped them so much that they told all their friends. Diary, she gave me a list of young men who want me to teach them how to be better lovers. After all these years I’m to be a teacher. It brings me to tears. I’m so happy. I’m sorry Diary, I have to go. The door bell is ringing.
Dear Diary,
My daughter’s boyfriend is so sweet. He is so devoted to her. Always doing nice things. I love watching them together, they are such a cute couple. I must admit to being a little worried though. Hard as it is to believe in this day and age, they are both virgins. They’re old enough to drink and haven’t had sex yet. I’m proud of them, but I don’t want my daughter’s experience to be ruined because Ricky doesn’t know what he’s doing. I’ve decided that I’m going to teach Ricky how to do it and maybe coach him through his first session with Diana. I’m just undecided on hands-on his instruction should be. I think I’ll speak with Diana and see how she feels about it. After all it is her virginity. LOL
Dear Diary,
So I spoke to Diana about her and Ricky’s relationship, about how close she thought they were to having sex, what questions she might have about the actual act, etc., etc. She was a little embarrassed, but the fact that I’ve always been open and honest with her in all our discussions helped her be the same. She is a little afraid of it hurting, but she is more scared of doing something wrong. After we discussed everything that could happen, and the fact that there wasn’t much she could do wrong during the actual PIV portion, we got out my dildo and I showed her some hand- and blow-job techniques. I have to say the girl’s a natural. Takes after her mother. I’m so proud. I also showed her how to put on a condom and impressed its importance on her, even for their first time with anyone. Start with good habits, stay with them, I always say.
Dear Diary,
Diana came to me today and said she had spoken to Ricky and that they would like me to teach him, but that they wanted to keep his virginity for her. I have to admit, Diary, that the thought of initiating that cute, young man into the ranks of the actively sexual is very arousing. All that smooth, muscled flesh and the innocence. Yummy. Just the thought makes me need my vibrator.
Dear Diary,
I spoke with Ricky today. He is quite eager to begin his lessons. I asked him what he had done so far. Can you believe all he has ever done is kissed a girl? Hasn’t even fondled a boob. Not even through a top. Amazing! I made him kiss me, just to see how well he does that. He was rather stiff at first. I guess kissing your girlfriend’s mother is hard to deal with. He’s not fooling me though, I saw his erection. He did relax when I reminded him that Diana had agreed to this. He wasn’t bad, a little mainstream. I showed him some tricks. I had to pretend not to notice when he ejaculated in his pants. I didn’t want to embarrass a very promising pupil, but I must say I really enjoyed the sense of power I got. Diana came to me later and thanked me. I guess he went to her to “practice”. LOL
Dear Diary,
Today I showed Ricky how to feel up a woman and make it seductive. I told him to kiss me and while we were doing that, I took his hands and had him feel my breasts and my ass. By the way, I must say his “practice” with Diana paid off. He’s a much better kisser. I actually got wet. I had him slide his hand under my top and slip it inside my bra. I soon had him thumbing nipples, rolling and pinching them and squeezing breasts like a pro. I even had a mini orgasm when he kissed and licked my neck. Such a fast learner. Diana also seems to be very pleased. She keeps thanking me.
Dear Diary,
Today we have progressed to taking off shirts and actually dealing with naked skin. Oh my, I haven’t felt muscles like those in years. It started out well but then youthful enthusiasm got the best of him and it turned into a bit of a mauling. I’m afraid I got very stern with Ricky and even spanked him a bit. I must tell Diana that he really seemed to enjoy that. I extended our session today until Ricky was able to treat breasts with the respect and reverence they deserve. Once he calmed down he was able to transfer his new kissing skills to my breasts. Quite divine.
P.S. I think he may need to throw out his underwear, he came many times. Ah, youth and its recovery time.
Dear Diary,
Ricky is progressing quite nicely. Today’s session reviewed all he had learned so far and added fingering the pussy with pants on. I had him stand behind me, while we stood in front of the mirror. I showed him how he could hit the erogenous zones of the neck and ears, fondle the breasts and play with the pussy all at once. I had him slide his hand down the front of my pants and tease my clit through my panties. I told him when the panties got soaked it was time to go flesh to flesh. It didn’t take long. While his fingers explored I explained to him what he was feeling and the different things he could do. I let him play as long as he wanted and rewarded his efforts with a massive orgasm. You should have seen the astonishment on his face when he realized I had cum. He was so proud of himself. Definitely got an A from the teacher.
Dear Diary,
Diana came to me this morning wondering what was wrong with her. It seems Ricky showed her his lesson and she didn’t cum. I explained to her that sometimes it takes a while for young women to have orgasms. That some people have an easier time than others. I said it would happen eventually as long as she didn’t stress over it. I asked her if she enjoyed it. She said she did for a while but then it got painful. I said that comes from trying to force it. She was so upset about her perceived deficiency, that I finally had to prove to her that she was capable of cumming. I had no idea my girl wasn’t even masturbating. I got out the lube and Hitachi and talked her through it. It took some time for her to find the placement and setting that worked for her, but when she finally did, she had such a spectacular orgasm, she spent the next hour in a daze. She was so beautiful, Diary, watching her was so arousing. If she hadn’t been my daughter I would have had to have tasted her and helped her out. As it was I had to go to my room and put my toys to good use. Does that make me a bad mother? I did warn her to not expect the same reaction with Ricky and to not rely too much on vibrators as they could make her less sensitive. The fact that she proved to herself that she could have an orgasm cheered her immensely.
Dear Diary,
It seems today is about reassuring young people. Ricky was also upset about Diana not orgasming. He thought he had done something wrong. After repeating my explanations, I had him show me what he had done. I even held back for a while to see if he changed his tactics when he got impatient. He was able to pull an orgasm from me even with me holding back. I told him not to worry, that he was doing fine. I let him practice everything for as long as he wanted. I must say I find teaching greatly rewarding.
Dear Diary,
We took a big step today. I taught Ricky how to pleasure a woman orally AND how to control himself a little bit so that he didn’t cum as soon as he was touched. After explaining how each woman was different, both in what her pussy looked like and what she reacted to, I stripped and lay on the bed. I had Ricky get up close and personal and explained what he was looking at. I had him get me off with his fingers so that he could see the changes my body went through. He was quite impressed with my clit’s ability to play hide and seek in its hood. Once he was comfortable, I had him lick me. We experimented for hours. Tonguing, sucking, nibbling, with fingers, without. I made him do everything I could think of. I showed him how to tell the difference between a “that doesn’t feel good” wince and an “Oh yes! Do that again” tremor. I lost count of my orgasms. Once I felt he was fairly confident I had him take off his clothes and I played with his cock. Diana will be pleased, he has an impressive package. He came as soon as I grasped his cock. I told him that would never do. Thanks to his quick recovery time we were able to work on his stamina. Although every time I added something new, we had to start over. I loved filling my mouth with his heavy cock and the reaction I got when I sucked his balls was delightful. We finished the session with a satisfactory 69 with me on top. Mmmm, yes, quite satisfactory.
Dear Diary,
Today was my last session with Ricky. I’m a little sad, but I’m pleased with his progress. He will make sure my little girl enjoys herself as much as possible for a first time. I made him keep his underwear on so that we wouldn’t inadvertently slip up, or in as the case may be. ;-P I showed him all the different positions and what benefits he could derive from them. I really wished that Diana didn’t want his virginity for herself, but promises are promises. Then we had a long talk about what he might expect from Diana. I told preparation and going slow would be paramount for her comfort and how he could distract her at the moment of penetration so that it didn’t hurt too badly and the pleasure outweighed the pain. Then I gave him a final kiss and left him to it.
Dear Diary,
Diana and Ricky came to me today and asked me to be with them during their first session. They wanted to make sure they did everything correctly. I tried to decline, I really did, but they were adamant. So I sat in a chair next to the bed and watched them come together for the first time. I tell you Diary, it was all I could do to keep my hands to myself. Watching those two beautiful young bodies experience sex and all its wonders was so beautiful. And the connection and love they shared brought me to tears. Ricky did me proud. He went slowly, just kissing her for a long time before removing her top and nuzzling her breasts. He soon had her moaning and begging for more. And when he took off her pants and knelt between her legs, I thought I was going to cum just watching him make love to her pussy with his mouth. She actually orgasmed and it was so touching how he just held her afterward. Then he removed his clothes and I saw a glimmer of fear in her eyes as she saw how big he was. I’m sure she was wondering how it would fit. She grabbed my hand and I reassured her that it would be okay. I made Ricky lie down and took Diana’s hand and stroked Ricky’s dick with it. I had her kneel over him and told Ricky to play with her clit. When she was writhing and moaning again, I placed Ricky’s cock at the entrance and pushed her down while Ricky pushed up. I made him stop and wait, still playing with her clit, until she moved on her own. Then Ricky started moving slowly and I left them to their beautiful passion.
Dear Diary,
Diana came to me today. She hugged me and told me what a wonderful experience she had. “Amazing” was her word. She said I helped them so much that they told all their friends. Diary, she gave me a list of young men who want me to teach them how to be better lovers. After all these years I’m to be a teacher. It brings me to tears. I’m so happy. I’m sorry Diary, I have to go. The door bell is ringing.
9 years ago