A 55-year-old Virgin

"I love watching a woman cum, especially when I've had a hand in it."

"Did I look normal when I came, like other women do when they cum?"

"Yes, you did, why would you ask that?"

"Oh, I don't know if I should say."

"Try me, Amy."

"I have never cum with a man before."

"What do you mean?"

"Just that, Jason, I have never let a man touch the erogenous parts of my body so intimately that I've cum."

"Really! You're not telling me you've never cum before?"

"No, I didn't say that. I have never cum in the presence of a man because before tonight, I have never let any man get close enough to put his fingers on my pussy."

"What? Any man at all? You mean, no man has ever got inside your panties?"

"How many ways do I need to say it? No, I have never let any man do what you just did with your fingers to get me to cum. Even my breasts, my nipples ... only you and one other man have ever sucked on them, but I never let that other man near my pussy."

"In your whole life?" I must sound incredulous, but I am. How could any woman go through 55 years of life and never experience a man in a sexual way? And why did she choose me now when she must have been celibate for all these years?

"So, you're a virgin then?"

"Hello, Jason, now you're getting it. Yes, I am, never touched, never entered."

"That's why you were so tight when I tried to finger you?"

"Yes! So, Jason, do you want to be my first, to initiate me?"

I gulp, never expecting this. My mind whirls, "Err ... I guess so if you want me to."

"You don't sound very excited at the prospect. I thought that was the big thing for guys to show off their manhood, their masculinity, by claiming that last barrier to a woman's body."

"Yes, I guess it was when we were in our teens. The prospect of deflowering a virgin looked to have passed me by when I married."

"So, your wife wasn't a virgin?"

"Oh no, she'd had her share of guys. Then again, I'd had quite a few girls by then."

"I should have let you claim mine back when we dated, Jason. Our lives could have been so much different. It is one of the big regrets in my life. I was very attracted to you, but I was raised with such high moral values that I considered myself too young to get on the sexual merry-go-round that most of my friends indulged in." The hand holding the bulge of my erection, still within my trousers, clamps tighter on me.

Interesting to hear Amy express her regrets now. I never saw her as being that intent towards me back then. But hey, we were twenty, and at that time, I was mostly thinking through my cock. After Amy, I had three more steady girlfriends that I, at times, thought might be the one before I settled down and married.

"Don't beat yourself over that, Amy. The past is the past and we can't change that. Seems like it's a good thing that I found you on Facebook."

"So, should I ask you again, would you like to take my virginity, Jason?"

This time, I gave her the enthusiasm she obviously expected at first, "Of course, Amy. A thousand times yes."

"Oh, that's much better. Oh, I should quickly add that it won't be tonight, in case you think we're about to do it. I want it to be something special, like a big event. Something to look forward to. For us, nobody else will know ... unless you choose to share with a buddy, that's up to you. I don't mind if you want to. But for me, it's momentous after all these years and I want to anticipate it and think about it for days before."

"I wonder if breaching the hymen becomes any more difficult when you're older? But whatever, I will make it happen for us both."

"I have no idea. That sort of fine detail is up to you. Your assignment is to take me and with a minimum of pain ... got it?"

"Yes, Amy. Is this why you've been reading Fifty Shades of Grey? To learn more about what happens in sex?"

"It is why I have been re-reading it this week, now that we have connected again after all this time. I first read it when it was first released, and it was more out of curiosity to see why the book was so popular. This time, it is my textbook," and she giggles. "So Jason, what about you?" She tightens her grip even more on my shaft to indicate she is talking about my obvious erection. "You have told me you haven't had any woman since your wife died?"

"That's right! Actually, I haven't had any sex since long before my wife died. She wasn't up to it in the last few months of her suffering, I guess it's been over a year since my trusty old cock has seen any action."

"Would you like me to do something for you tonight? You know, to make you feel good just as your lovely fingers did for me? One good turn deserves another."

"Oh, that's an exciting offer. Yes, of course, but only if you really want to do it. I wouldn't want you doing anything that you didn't like."

"I wouldn't have offered if I didn't want to. I told you, Jason, I've been using Fifty Shades as my textbook. I may still be a virgin, but I've learned a few things that a woman can do to have her man feel good."

Amy moves her hand but only to grasp the fly zip and pull it down. That hand reaches in, foraging around in my underwear and pulling out my hard erection. I look down to see her wrapping her hand around my shaft, sliding it up and down, "Is this how I should do it?"

I draw in a deep breath to cope with the effect her appealing soft caress is having on my shaft, "Yes, you got it perfectly, just like that is great."

She wanks my erection several times, and then pauses. Still holding it firmly in her grasp, Amy asks, "Would you prefer me to use my mouth ... err, I mean like I could give you a blow job? That's what it's called, isn't it? Would that be better for you than my using my hand?"

"Amy, you do know, don't you, that a blow job is when you get as much of a man's cock as you can fit inside your mouth? But you don't actually blow, you suck on it."

"Yes, I've read about that. Do you want me to try?"

I couldn't believe I was in the midst of a sexual lesson for a 55-year-old woman, "Of course I would, what man wouldn't want that when it's offered, but are you sure, have you thought this through?"

"What do you mean, what's to think about? I told you I've been reading Fifty Shades."

"Well, I don't want to raise any negatives at all, but since this has the potential to be a long and wonderful relationship, I want to be totally honest with you. Some women hesitate to give a blow job because of what else the man's cock does. You know, a guy pees out of it, and I guess that puts some women off. I can assure you I did shower before coming here tonight, but I did use your toilet for a pee while you were clearing the table after dinner."

"I thank you for your thoughtfulness, Jason, but I have considered it thoroughly, even talked to my bestie. I planned to do it for you tonight anyway, but after how you made me cum before, I especially want to do it now."

"I'm happy if you're happy, Amy."

"Jason, I may be an old virgin, but I do read a lot, and I'm a big girl now. Anything else you want to tell me before I give my first blow job ever?"

"Err, yes there is. You know that the ultimate purpose of a blow job is to get the man to cum ... that will be an absolute certainty when your lips and tongue become too much for me to hold back. I do sometimes release quite a load, particularly now that it's been so long. I've never tasted cum, but my wife always told me how much she loved doing it. I have dated women when I was young who didn't like the taste and insisted that I warn them when I was about to cum and they would pull away. Even one woman who would accept it into her mouth but refused to swallow, she hated the prospect of semen in her stomach, so she would spit my cum out."

"Jason, if I were to pull my mouth away just as you cum, wouldn't that spoil the whole thing for you?"

"Yes, it's nowhere near as good as blowing into a warm, wet mouth."

"Jason, I want only the best for you, so there's no way I'll pull my mouth away until I have all of your cum ... and then I should swallow it all, is that right?"

"Darling, you are heaven-sent. Yes, that would be the ultimate."

"Ok, I'm ready if you are?"

I see her lovely smile before her head drops into my lap, pursing her lips and slowly sliding them over the head of my erection. Amazing! But then a pause, lifting back off. Already her mouth feels good, and I want to scream out, 'don't stop,' but she pauses only to say, "Tell me if I'm not doing it right, I need your guidance and advice so I can do it better than any other woman has ever done for you." Then, her lips close back over the head and slide down to half cover my hard shaft.

I do impart a tip or two along the way but generally, she has her technique right. Amy has taken in whatever she has read because, for a novice, she is extremely good. She even tries to deep throat me but gags when she attempts to sink more than two-thirds of my core inside her mouth. A muffled sound emits and her eyes water as she tries to take too much of me in.

I try to hold back as long as I can to enjoy Amy's first blow job to the fullest, but her warm wet mouth is enticing and, after about 5 minutes, I feel an overwhelming urge to let go and cum. I even hump my hips upward a couple of times, but I don't want to scare her by jamming too much of me inside her mouth.

She has agreed that she wants to take it all and swallow, but I feel an obligation to alert her. Once I feel my release is imminent, I call out to Amy, "I'm cumming."

She mumbles something unintelligible because her mouth is so full of me and seems to intensify her furious sucking of my cock. I reward her effort by blasting a powerful release, my cum spasming from the tip of my cock deep to the back of her throat. I hear a muffled grunt as she feels my creamy deposit hitting her tonsils. Amy never lets up until her lips and tongue have drained me. I have nothing left to give ... for now. She slides her mouth up and off my cock, her tongue licking her lips to capture any residue.

"Like a pro," I thoughtlessly suggest.

"Have you ever been to a pro?"

"No, never!"

"Never wanted to or never needed to?"

"Both, I guess. You were excellent, did you learn all of that from a novel?"

"Err, not quite, Jason. We do have a lot of how-to books in the library, some that only a librarian would know about, and I did ask my brother's wife for advice. He's always telling me how sexual his wife is."

"Really, you're full of surprises."

"Jason, I hinted at it before, but I do have serious regrets that I was so stupid to let you go when we dated. I thought I wasn't ready for the sexual demands of a 20-year-old boyfriend, but I hadn't realised how much you meant to me. When you posted that message on my Facebook page, I couldn't believe my luck. I had never expected to see you again. After we talked on the phone, I knew my life without love, without sex, was about to change in a good way. I was determined not to let you slip away this time. I am ready to give you all of me."

"Wow! That's a big call."

"Jason, do you know that the cock I have just had in my mouth is only the second I have ever seen ... in the flesh, I mean. Like, I have seen them in movies, but yours is the first I have touched."

"Whose was the first one you got to see?"

"My father's, and only a few years ago. Poor old dad got Alzheimer's, didn't know us and didn't know much of what he was doing toward the end. He used to walk around with his cock hanging out of his pants whenever we had a family gathering. Sometimes, he even had an erection. That was embarrassing because we all wondered whether any of us women in the family inspired it. I have to tell you that I loved your cock, loved having it in my mouth, loved sucking on it to make you feel good. It must have worked, you sounded and looked like you enjoyed it, and there was so much cream for me to swallow."

"You were great, honey. Just perfect!"

"I had no idea what to expect ... you know, circumcised or not, long or short, thick or thin? Of course, I have nothing else to go by, but to me, it's great and I know I'm going to love the feel of it going inside me ... oh, perhaps not the first time, but after." She gave that cute little giggle again, "Your wife was right too, you do have nice tasting cum."

"Amy, sounds like you could have been planning for something to happen tonight. We have barely kissed since we started dating this time, so that was a big jump to expect to see my cock tonight."

"I guess so, but I remember how sexual you were back when we first dated, so I knew it would only be a matter of time before you would want to kiss me and kiss my breasts too."

"So, you've been waiting for me to make a move. Was that why you invited me to dinner? To hurry me along?"

Amy gives me her best innocent look, "Could be! Oh Jason, I so want you, want this," and she squeezes what remains of my erection. "Ooh, it just jumped."

"It's reacting to your sexy talk and your touch."

"Does that happen a lot?"

"Yes, whenever you say something really sexual and if you were to appear naked in front of me."

"No full nudity tonight, I'm saving that for our special night. So, I hope you're going to leave here tonight feeling very satisfied."

"I was horny when I came here tonight, have been for most of our first four dates. You can be very proud of what you did for me tonight. I feel very, very satisfied ... thank you, Amy. So, is there a date yet for your deflowering?"

"I need to think a lot more about that. How do you feel about it, Jason? You haven't said much about my gift. Or do you not see it as a gift, is it more of a burden or a challenge? I guess you've never had a virgin before. Are you ok with doing it? If you have any doubts, maybe I could ask my doctor if there is some minor surgical procedure he could do to rid me of my hymen? I don't want you to stress about doing it. Tell me if you'd rather not."

I couldn't get my mouth in gear quickly enough, "NO, no, I'm good. I've never had a virgin before, but I'm sure I can take care of it. The reward for both of us will be the great sex that will follow, heaps of pleasure."

"I hope so. That's good, I'm pleased you're ok about it. My god, I never expected to be in this position. Once I'd reached 40 and hadn't had sex, I thought I'd be buried intact and untouched."

I finally withdraw my previously roaming hand from under her skirt, and Amy lets go of my now flaccid cock. I push the remains back inside my underwear and zipper up. Meanwhile, Amy is securing her breasts back within the cups of her bra.

When I was driving here to Amy's house for dinner tonight, I harboured a hope that I may even get invited to stay the night. That isn't eventuating, nevertheless, the evening has been a huge success, and with much promise ahead.

I bid Amy goodnight, thank her for a wonderful dinner and for her magnificent and unexpected blow job. I call her again the next day and she tells me that she feels very good about us as a couple. It is moving very fast, but I have no regrets. I liked her very much when we dated as 20-year-olds and consider myself fortunate to have found her again.

We go for a picnic by the lake on Sunday. After lunch, we stroll hand-in-hand along the water's edge and Amy reveals, "Jason, that was a stupid suggestion of mine to have a doctor remove my hymen. I am totally rejecting that. It is you or nobody, and I am certain that you will introduce me to the joys of sex as only you can."

"Thank you, I will admit that I wasn't too happy with leaving it to some outsider. Have you thought of when, is there any reason why we need to wait?"

"No, none at all, really. I guess the only reason that I didn't want it to happen on Friday night was that I wanted you to have time to absorb the news that I am still a virgin. I was so eager to see your reaction. You are such an honest, straightforward man that I knew if you had any doubts about us as a couple, you would express them before I give myself to you. I want to give you this, something precious that I have held sacrosanct for 55 years."

"No, I love that we have found each other again, and I am honoured that you chose me to initiate you into the wonderful pleasures of sex."

"Good, then there's nothing to wait any longer for then."

I half expect her to ask me to take her home and complete the job tonight, but instead, Amy asks, "How do you feel about coming to stay over this weekend. I'll cook dinner for us Saturday night and you can take me to bed, claim my virginity, and show this innocent maiden how good making love can be."

"Sounds great," I confirm.

On Monday, I call my closest buddy, we have known each other from school days. "Hi Matt, I need some advice from you. I seem to recall many years ago that you told me how you had a virgin ... you know, back when we were footloose, getting around with lovely young singles."

"Yeah Jace, I did. Why do you ask, buddy? Don't tell me you've found some young chick, and she's a virgin. Man, are you cradle snatching now?"

"No, you're not going to believe this, but I have been dating a woman of my age and, incredibly, she's never had a guy ... inside her, I mean."

"What the fuck, are you sure? She's not pulling your chain, is she?"

"No, genuine man, she really is a virgin ... a 55-year-old virgin."

Since we've been friends since school days, Matt would remember me dating Amy all those years ago, but I am not about to reveal who it is to him out of respect for her privacy. He will eventually find out who it is when I tell him we are regularly dating.

"So, what do you want from me?"

"Well, you've had one, I never have. I recall when we were kids that we used to joke around, tell each other how good it would be to have one. Now that I'm faced with a grand deflowering, I'd like some friendly advice, any tips you can impart."

"Really? Oh, buddy, that was so long ago, hang on, let me think. Yes, I remember it wasn't completely cut and dried, so to speak. Her hymen was really tough, and I couldn't break through initially, and she panicked, started screaming the place down, telling me how much it hurt. I had to stop for a while. I gave her some time and some soothing and encouraging words and then, about an hour later, we gave it another go. It was still tough pushing through, but this time I succeeded."

"Thanks, Matt, not exactly what I needed to hear, but thanks for your honesty."

"Do you have any plans when this is going to happen?"

"This Saturday night, I am staying over at her house."

"And she's ok with your plans to do it, Jace?"

"Not my plan, Matt, it's her plan."

"No shit. Man, you sound like you've lucked into a good one, if she's held out all these years and wants to give it up to you. All the best, good buddy."

I did Google virginity during the week, read about as much as I could to prepare me for the coming event. The big day arrives. I shower at five, dress and turn up at Amy's house at six. I carry with me a small overnight bag, but don't expect to use the pyjamas in it. When she swings the front door open, I am amazed to see her standing there in a flowing negligee, somewhat see-through. It seems so out-of-character for the demure virgin librarian.

"I feel overdressed," I tell her as I step across the threshold and take her in my arms to kiss her fervidly.

"Oh, Jason, it's so good to see you and hold you. I've been nervous all day, literally shaking at times. I nearly called you twice to ask if we could postpone it. I don't mean the dinner; I mean the afters. I'm worried that I placed too much importance on the occasion. I should have just let it happen instead of planning for it. We may have been better to be just making out sometime at the end of a date, and I would be so overcome with the heat of it that I would open my legs, and you would take charge and do me."