tagMatureVirgin Man's First Sex

Virgin Man's First Sex


This story happened not so long ago. I was 20 years old working as an intern for a communications company in New York City. At the time I was a student at NYU going to classes in the morning hours, and interning the rest of the afternoon. As an intern, I was basically a glorified gofer. Bringing coffee to the boss, filing paperwork, answering the phone, and assisting in work no one would ever want to do.

I was working with this company for a couple of months, and I absolutely hated it. The only reason why I didn't quit was because it's worth 3 credits at college; otherwise I would have been out the door.

This story begins late one winter Friday afternoon. I just finished a grueling calculus exam. I didn't study as hard as I should have and needless to say, I knew I failed. In order to pass this class I knew I would have to Ace the final exam, and that alone worried me. How can I put my self in such a position?

An hour or so later I walked into the company building, distraught, aggravated and depressed. The last place I wanted to be this very moment was in this place, but I now needed these 3 credits more than ever. I took the elevator to my floor, punched in, and started filing paperwork, neatly piled for me. About 20 or so minutes later my boss called my name.

"Jack, I need you to bring this package down to the mailroom, it needs to get out today."

"Yes, sir" I replied.

"But Jack, you have to wait until it's picked up by the carrier, I don't care how long it takes, wait there"

I was about to tell him to bring the fucking package down himself; I politely complied, picked up the "five ton" package, and brought it to the mailroom.

The elevator carried me down to the basement level; I walked to the steel door labeled mailroom, and rang the bell. A few seconds later the door opened, and I was introduced to the Mailroom Supervisor, Ms. Betty Taylor. At the time I assumed she was in her late 40's. Her eyes were dark black, however looked maternal, warm yet focused. She had long frizzy black hair, and beyond a few slight wrinkles caused by age, her skin seemed soft beyond her light facial complexion, only subdued by her slightly red lips. As I looked beyond her face, and focused on her body, beyond the dark button down shirt and khaki pants she was wearing, I saw a perfect specimen of a slightly overweight woman, whose weight was perfectly proportioned. Her breasts seemed most ample, her thighs and ass thick. As she walked, her body didn't jiggle, but was as firm as that of a young skinny 20 year old. She stood at about 5'6".

As we made our introductions and I explained the situation to Ms. Taylor, she informed me where to place the package, offered me a seat and a cup of coffee. As I sat down, she sat across from me, and asked where I went to school. The name badge I wore on my lapel gave away that I was an intern, so I answered her. She then asked how I was doing in my classes, and it was then I answered "alright" in a completely upset tone of voice. She then knew something was wrong and tried to fish out the answer, I then told her of my miserable exam in calculus, and how I didn't study.

"Well dear why didn't you study," she asked in that motherly way.

"Just busy I guess," I answered.

"Come on, busy with what, what's more important than your studies."

"I guess I just have other things to deal with."

"Girlfriend, isn't it," she immediately said, with out doubt.

"How did you know," I asked surprised.

"When you're my age dear, with 2 grown boys, and a girl, you know these things, so what's wrong with you and your girlfriend."

I wasn't sure how to answer, if I answered honestly, I would embarrass myself, and if I lied, she would probably know.

Betty smiled, and said she knew what it was.

"What," I asked; as if she would know?

"Sex, it has to be sex, something to do with it, not to do with it, but sex nonetheless."

I couldn't help but smile, I found her amazing, and she was like some kind of soothsayer. At least back then I thought she was, as I got older I understood how she knew so much.

"So dear what is wrong with your sex life."

"What sex life," I answered.

"What do you mean?"

"She says she wants to wait till she's married, so we don't have sex, barely even kiss."

Betty nodded her head, and offered that motherly assurance. "But sweetheart, if you love her, it shouldn't matter."

"I do care for her, but I'm not sure whether I love her, I just, I... I'm sorry, it's just to personal."

"What, what is it, what are you afraid of?"

As the conversation continued she tried her best to get me to spill my guts, she kept asking question after question. She crossed her legs, placing her right leg over her left, and mildly shaking it. After about 5 minutes, I eventually cracked and admitted that I was a virgin. Oh the shame and agony a 20 year old man admitting to still being a virgin, and admitting it to an old lady, I only first met half an hour ago.

"Oh dear, now I get it, now you're with this girl, and she won't give you any, and your horny body can't take it."

I agreed and we laughed. About a minute or so later she asked me if I ever felt her up, and I explained that my girlfriend was almost flat chested so really there was nothing to feel.

"She's not as big as me then, huh."

I stared at her chest, agreed, and then immediately caught myself, and showed an obvious sign of embarrassment.

"It's ok, you can stare, I can't remember the last time a young good looking man like you stared at me."

It was at that moment the most peculiar, erotic; stimulating act ever occurred to me, she started to unbutton her shirt. I wanted to ask what she was doing, but some unknown fear prevented me from opening my mouth.

"You want to see my breasts," she said.

"I...I..." I was in a complete loss of words.

She laughed and her shirt was completely unbuttoned. She wore a black lace bra, her cleavage protruding out. If I were to put my hand between her two enormous breasts, my hand would enter invisibility. Then she grabbed the tops of the cups of her bra, and brought them down. Boing. Her two breasts hung over her bra, visible to my virgin eyes. They were huge, each sagging to her thighs as she sat down. Later I would learn they are GG's. What was more exhilarating were her nipples. The areolas were a dark brown, the size of pancakes, and in the center were her nipples, each about an inch long and thick. As I stared my cock hardened, pushing against my pants.

"You like what you see," she erotically asked.

"Oh yes," I answered.

"Stand up and come here sweetheart."

I stood, and she placed my hands on her breasts. Slowly moving my fingers along the sides, ending at her nipples, rubbing them with the palm of my hands. She closed her eyes, tilted her head back, and had a look of ecstasy. Here I was turning on this 40 something year old lady. Then I felt her hands unzipping the fly to my pants, at this point I just about came. She reached in and grabbed my cock, lifting it out cupping it in her hand.

"Wow, sweaty you have one big beautiful young dick."

Her lips opened, and she aimed my 8" cock inside the warmth of her mouth. The wet walls of the inside of her cheeks and the roughness of her tongue moving around the base of my manhood was more than my young cock could take. As she made love to my dick, within seconds I was ready to cum. I said stop, knowing I was going to cum, she stopped, and put my dick between her cleavage, and worked her breasts up and down.

"Stop, please stop, I'm going to cum"

"Cum, baby cum, let me taste your cum"

At that moment I ejaculate a waterfall of cum, her mouth opened and she swallowed every drop. She licked the head of my numb cock, pulling on my balls, draining every last drop. I was about to faint.

"How was that?"

"It was great, I can't believe it."

"Believe what, this is just the beginning."

As I put my cock where it belongs, and zipped my fly up, she quickly buttoned her shirt, walked to a table, grabbed a pen and paper, and scribbled something down.

"Here is my address, come over at 8:00, and we will finish this."

"Finish," I asked.

"Yes my dear, your gonna make me cum next."

We passionately kissed, her tongue and mine together, her breasts against my chest, my cock beginning to hard again, and then the phone rang, she answered, the courier is outside to pick up the package. She said see you soon. I knew this would be a night to remember.

A few hours later, I was on the subway making my way uptown to the home of the lady I would be losing my virginity to. What was I thinking, she was twice as old as I was, really not that attractive, I mean, she wasn't ugly, just old, she was fat, in the conventional sense, she really looked like a soccer mom or something. Yet I wanted her, wanted her so badly. Couldn't wait to feel her mouth on my cock again, touch those enormous tits, lick those finger tip size nipples, and most of all feel my cock inside the wetness of her pussy. I was going nuts as I left subway walked a few block and made my way to her apartment building. I rang the bell to her apartment, was buzzed in and made my way to her door, before I could knock the door opened.

She looked different than when I saw a few hours ago, she was only wearing a white bath rob, tied around the waist. Her hair was wet hanging over her shoulders, and her face too was wet, and was pure natural, no makeup or tint. She came to me and kissed me passionately. Then in a dominate voice asked me to follower her. We walked into her bedroom, she sat at the edge of the bed, at this point I thought she wanted to suck me off again, I was about to take my pants off, when she said:

"What do you think your doing, now it's my turn."

She opened the rob revealing her complete naked body. Her breasts sagging as I remembered. She laid back on the bed and spread her legs, revealing to me her pussy. She had a hairy pussy, dark and thick. It almost reminded me of Kay Parker in the old porn movies. But what was more marveling was the pussy itself. Never in a magazine or a movie did I see pussy lips as thick as hers, hanging down from her clit, if she stood they would hang at least an inch. And her clit, oh my, her clit, you thought her nipples were huge, her clit made them look small. It was like a golf ball. She grabbed my arms and said eat-me, eat- me now.

I've never gone down a woman before, so I was definitely nervous. I moved my mouth towards to her love mound. The smell of soap and must was exhilarating. I first started to nibble on her lips, and use my tongue to go up and down her clit. I then started to suck on it like a lollipop. She tasted sweat yet slightly bitter. She then said, "hunny do me a favor, use the middle of the top of your tongue and move it up and down my clit. I did as I was told, and after her positioning my head just right with her hands, and a few more tutelage lesson from her, she was moaning like crazy. Her thighs were tightening around my check bones, as I hastily moved my tongue against her clit. Her screams became louder, her thighs tightened more, almost to level of pain, her hand pushing my face deeper insider her pussy. Within in a few moments later, she yelled that she was going to cum. And then it happened, never have I seen on any porn movie, read or heard of what she was going to do. She lifted her whole body up, and came, literally came jizm all over my face. Out of her pussy squirted this white creamy sweet cum. After the moaning subsided my face was covered in white cream. I lifted my head from her pussy, looking at her confusingly.

"Very few girls can do that my dear, I'm what they call a squirter."

"Wow," I said, in a loss of words.

"I haven't cum like that in ages Jack, you are great." Betty said as she tilted her head back, rubbing her breasts and then feeling her numb pussy, with a huge smile on her face. "It's been so long a real man ate my pussy like you have."

I was proud of myself, but also very horny, and after 5 or so minutes, she never mentioned having sex, so I thought I pleased her, and she was done. I got up from the bed, still fully clothed, and started to walk away, when she commanded me to get naked. I did as I was told, and then she stood up from the bed, and asked me to lay down. I laid flat on my back on her posterpedic mattress, and she starting sucking on my nipples. Her tongue ended at my cock, which was hard as a rock. She grabbed my throbbing meat in her hands, and commented that she has never seen such a beautiful, long, thick, young cock. She slowly jerked, and felt it throbbing, and then said she didn't want me to cum yet, but cum in her pussy. She then straddled her body against mine, and led my cock into her moist pussy. Her pussy was hot as hell, and so wet my cock glided right in, I grabbed her beautiful breasts, sucking at her nipples, as she trusted about 10 or so times, nice and slow, and then, I couldn't hold it any longer, and I came inside her. She pushed my cock deep inside her as I came, and she moaned louder than I, and again she had another orgasm, squirting her juices all over my stomach. She laid by my side, and I apologized for cumming so soon.

"It's ok hun, you're a beginner, you'll get better I promise."

Sure enough I did, we fucked that night 4 more times, each time lasting longer. She continued to teach me how to be the best fuck machine in town. We fucked in every position, practiced domination, and even took part in anal sex. And sure enough our relationship lasted for many years. Eventually we both got married, her remarried, but we continued our affair for a long time. I've been told I am a great piece of ass, and I know I have her to thank. Thank God for older woman, who take young men into tutelage!

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