I am glad to have helped my daughter's best friend. Who knows, maybe she will take me as her substitute boyfriend someday, if I play my cards right.
I have always been faithful to my wife, even in light of what happened recently, which is the subject of my story. When my daughter was in the second grade, she developed a friendship with cute little Melanie and it continues to this day. They are best friends.
Melanie is quite tall. She reached 5'8' as early as 14 years old. Presently, she is 20 years old, 5'9', very thin, about 30A-20-32 in my estimation. Her tiny tits have teased me for years and I'm glad they seem to have stopped growing at size A. I always liked it when she came home with my daughter, especially for sleepovers. Sometimes she dressed very provocatively, showing off her long legs and bare midriff. On more than one occasion I managed to sneak a peek down her top. In the summers, she often came over wearing flip flops which she kicked off inside the house, as if to tease me to distraction with her long thin legs and pretty, shapely feet, in addition to her other charms.
Sadly (in my mind), she paid me no attention whatever. In her eyes, I must have been just my daughter's doddering old father.
I knew that Melanie was having relationship problems with her boyfriend. She and he have been sexual together since high school, but outside the bedroom, they often seemed to fight. She wanted him to pay her more attention and he wanted some space. She was too clingy for him and he was too aloof for her. Classic dynamics, I thought to myself.
A recent flare-up left her in tears when she came over to commiserate with my daughter. I could hear from the bedroom her occasional sobs between their murmuring voices. I managed to gather most of the salient details through the door. But don't accuse me of eavesdropping because.... well.... OK, I was eavesdropping. Who could resist?
When they emerged from the bedroom, I told Melanie that my shoulder was always available for her to cry on any time she needed it. (Her parents had divorced when she was very young and she had no father figure. Her relationship with her mother was rocky at best.) She looked at me oddly for a moment then thanked me and left.
A couple of days passed and she called me to ask if she could take me up on my offer. Of course I told her to come over.
When she arrived, I could see in her face that she had been crying. She looked so vulnerable. The most impure thoughts crossed my mind. I offered her a spot on the sofa and we sat down together. She leaned her head on my shoulder and started to sob. I held her hand and basically listened without saying a word, just stroking her hair and comforting her as she recounted her tale of boyfriend woes. It seems he cares only for his own pleasure and never gives her an orgasm. I was surprised, pleasantly so, that she was telling me this. I would be lying to say my dick hadn't hardened up, uncomfortably so.
After she talked herself out, we just sat there a couple more minutes, my arm around her shoulder. I was holding her left hand with my right. Out of nowhere, she looked up at me and asked if I have a good relationship with my wife. I said yes. And she said 'No, I mean sexually?'
After a moment of disbelief that she would ask something so personal, I told her we have our share of problems but that when we have sex, I always attend to her pleasure before my own, because once I cum, I fall asleep. What can I say? I do. I'm not so young any more. So I have to give her an orgasm or two before indulging in my own selfish pleasure. If not, she is left in frustration with nothing to do but go solo or forget it.
She asked me how I do that and I said usually I masturbate my wife until she cums, then climb on top of her. If she doesn't want intercourse, I will masturbate myself while she caresses and kisses various zones that feel good.
Melanie apologized for getting so personal and I told her it was okay, I was glad to help. I gave her advice about being more assertive in bed and getting her boyfriend to do what she wants. And if he won't, to cut him off from her favors until he changes his ways. Or simply dump him.
Then she did something that knocked off my socks, literally: She looked me in the eyes and said 'Would you give me an orgasm the way you do it for your wife?'
I pretended to refuse, citing my marital vows, the age difference between us (which to me wasn't an issue) and anything else I could think to stammer out. But she argued that I wouldn't be unfaithful because we wouldn't be having intercourse. (Dammit!) Then she confided in me that she already spoke with my wife and got her permission for me to diddle her.
I didn't believe her. She told me to call my wife and just say 'Is it true?' So I texted her cell: 'Is it true?' to which she replied 'Yes but nothing more, she needs it' 'OK, thanks Sweetie, you're the best.'
I looked back at Melanie and she locked eyes with mine and started to unbutton her blouse. She was wearing no bra. Like a fool, I just stared, not believing what was about to happen. She stripped down to her panties and was about to take them off and I said 'Stop, leave them on.' I stripped to my briefs, took her by the hand and walked her to the bedroom.
I laid on my right side and directed her to spoon up in front of me. I started lightly caressing her, my hand slowly running a circuit to include her tiny tits, stomach, hip and thigh (coming close but not touching her pussy). I did this for a few minutes to get her relaxed and feeling good. At the right time, I put my arm tightly around her waist and rolled onto my back, pulling her on top of me, facing up. I positioned my dick, now harder than it has gotten in years, between her cheeks to lessen the painful pressure of her weight pressing on it. I told her to hold onto the headboard with both hands and to spread her legs. I proceeded to caress, with one hand, her delicious tits so invitingly exposed, while with the other hand explored as far up and down her nubile body as I could reach, but not touching her pussy, though getting closer to it each time I passed by that area.
Eventually, I zeroed in on her pussy, lightly masturbating her over her panties, rubbing up and down the length of her slit, circling around, occasionally sneaking inside her panties for a rub around her pussy directly on the skin. Gradually I increased the pressure and focused my ministrations on her clit and slit. I developed a rhythm and kept at it. My other hand was still playing with her titties alternating between them and tweaking her nipples.
We kept that up for some minutes until her breathing deepened and quickened as she entered the throes of her orgasm. I continued masturbating directly on her clit and lightly teasing around her nipples for at least a full minute while she was bucking her hips, contracting her abdominals and softly moaning with each exhalation. It was far more exciting to me than when I do the same thing to my wife.
When her orgasm subsided, I rolled back onto my side, bringing her back down, spooned in front of me. I hugged her intimately, hands on her tits, and let her come down gently and warmly. Her hand went to her crotch and she lightly masturbated herself while coming down.
I whispered into her ear how much I have lusted after her and told her that I had dreamed about doing that to her since her adolescence. I also confessed that I had cum in my underwear while she was cumming. I apologized for making a sticky mess on the back side of her panties. She cooed how good it felt and thanked me for being so kind and not to worry about the mess. She said that she now understands what her boyfriend problem is. She said she wished I was her boyfriend.
Wow, what a shock! Of course it can never be, but let me tell you, it's all I can think about now when I masturbate or have sex with my wife. I told her (my wife) about that. She seems open to letting me help Melanie again if she ever asks for it.
I think I can encourage that along somehow and if I play it right, maybe I can acclimatise my wife to the idea of letting me serve as Melanie's substitute boyfriend. Ultimately, I hope it develops into a full-on sexual relationship, for if ever I get that green light, there will be no stopping us.