It's A Girl's Life Ch. 01

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The night I lost my cherry.
5.6k words
4.12
90.9k
27

Part 1 of the 3 part series

Updated 10/06/2022
Created 07/03/2011
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True story!

Greg greeted me in a very shy and timid manner when I opened the front door to him while I was desperately hoping that my own nervousness wasn't too apparent to him.

Earlier on in the afternoon, I'd spent a few hours getting ready with the help of my old lover Cathy, who'd come round to offer moral support and a few new makeup tips to help me get ready for my big date. I've known Cathy now for about 9 years now and though we're no longer lovers, we have become the very best of friends.

Years ago, Cathy had came home one night and caught me walking round our unit in slinky lingerie and after the initial stunned silence followed by the inevitable temper tantrum, had calmed down enough to try to allow me to explain myself. In the end she finally accepted and realized, that I was far happier wearing women's clothes then men's and that my feminine side was starting to take control. The end result was 1 ex-lover who was somewhat shitty with me at first, but eventually and very surprisingly considering the circumstances, 1 great and longtime best girlfriend.

Over time she'd come to accept my lifestyle change, although the initial split up was far from pleasant. As time passed, we stayed in touch and were always there for each other, especially when she needed a helping hand financially or an emotional shoulder to cry on after various boyfriend breakups, to the point where she finally came to look at me, not an ex lover, but as a loyal friend. Over the years that turned into what we had now which was a very close friendship where we were always willing to answer each others calls for help or advice or to borrow clothes without question or hesitation.

It was, through her efforts earlier in the afternoon, that I had been made to look 'very' femininely attractive...for a 30's something male. In fact the make up suggestions were so good, I actually looked totally feminine and it was only the voice that gave me away. She'd not only helped with makeup ideas for this evening, but helped me critique and choose my clothes for the date.

Her sarcastic comments when I put on a white smooth front bra which, by the way, had had soft gel inserts that gave me a 34C cup bust, turned to ribald suggestions when I put on a white satin suspender belt and silk stockings. But she was completely speechless and the look on her face was priceless, when I reached into my underwear drawer and pulled out a pair of electric blue silk crotchless panties before putting them on.

"Couldn't find a pair in white to buy" I quipped to her, as I wiggled them into place. "The damned problem with them is that they may look sexy, but where do I put my prick? It's got no support for my balls down there at all!"

"I always thought that you'd be a slut, if you were a woman" she laughed, as I paraded around in front of her showing my underwear off.

The dress I'd picked out and we both agreed was hot on me, was of a long flowing white silk with a slight lining built into it, so while it was not diaphanous, in places or with certain lighting behind it, it hinted it was and while near floor length, the split at the front was over lapping and parted to about midway between knee and thigh so it showed off a fair amount of my legs when I walked or sat down. The top half of the dress was cut in such a way that with my bra on, it also emphasized my bust as well. The obligatory 3 inch white strappy stiletto heels and the auburn colored wig which came down and curled onto my shoulders finished off the outfit.

Cathy had brought around some of her jewelry for me to wear, including a gorgeous imitation diamond choker necklace, which not only drew attention away from my legs and upto my neck but with the cut of the dress also drew attention to my bust as well.

"GIRL, I'm thinking that you won't need to borrow my clitoris clamp," Nicky laughingly said as she showed it to me before putting it back in her purse.

A small white shoulder handbag completed the picture so when I looked in the mirror, I actually liked what I saw, which was a woman who was nice to look at, not a raving beauty but easy on the eye, 'definitely' feminine and with a good figure. I knew a few men who would have looked twice at me, with the sole intention of dragging me into a bedroom and ravaging me, but the person I was hoping who would do that was Greg.

"You look DEFINITELY fuck-able merchandise Nikki. If I was a guy, I'd give you one!" Cathy admiringly told me.

I 'knew' that I looked desirable and believable too. Not like those TV's I've seen coming out of clubs late at night, sporting outlandish sized boobs, the long blond wigs, the tight short skirts and legs that come up to their arse, that the skirts never quite seemed to reach down to cover and screamed to you they were men in women's clothes.

I was sure that Greg wouldn't regret being seen with me dining in public, or for that matter...in the morning. That's if there 'was' going to be such an eventuality as me staying overnight at his place. And I knew it just HAD to be tonight or never. Greg had been dating me for about 6 months and he never rushed it with me. He knew of my thoughts on sex and although I did keep him interested with the occasional BJ, I wasn't sure until only a few weeks ago that he was THE one to take my cherry. He'd even had a medical to show that he didn't have any little nasty's and I'd more than hinted that tonight was going to be special for both of us.

Cathy reminded me to take a spare pair of knickers and a panty napkin, as well as my makeup in my purse. "Just in case you stay the night at his place. You'll need a change of knickers in the morning and the napkin is for emergencies!" she smilingly said. "Hon, I know you're a little bit nervous at the moment, but just keep your voice soft and demure, take your time, act timid, always concede to the guy, enjoy looking and feeling like a woman and you'll have a great time," Cathy said as the doorbell sounded.

"Good luck, girlfriend" whispered Cathy and slipped into the bedroom while I went to the front door and opened it.

When I saw the look of absolute amazement on Greg's face I felt all my fears vanish.

"Wow....you look positively gorgeous Nikki" he said, handing me flowers he had held behind his back.

I recalled giving flowers to a lot of my dates while I was still straight. But I'd never expected it too happen to me. Holding the bouquet in my hands made me start to slip into a girlie, mushy frame of mind. It got even better....he actually asked if he could hold my hand as he escorted me to his car. Opening the car door for me, he then gently leaned over me to pass me the seat belt and the smell of his cologne and the proximity of his body had me thinking, that if I was a real woman, I might be getting damp panties about now.

The restaurant he picked was excellent. Quiet, but pleasant, well cooked food and the way 'he' behaved and how he treated me throughout meal definitely had me in an aroused mood and very girlie feeling. Even my little penis was leaking a little bit, so I guess I was getting a bit damp.... down there!

With diner over, we got up and danced to a few tunes. My body molded against his, my head against his chest, while he had his arms encircling my lower waist, occasionally having his hands slipping down to caress my bottom.

He smelt so good, felt so warm and strong and just 'so' male and I felt safe in his arms and it felt so nice.......as we danced to the music. His occasional soft kisses on my neck were turning my legs to jelly so much, that I was almost clinging to him to avoid collapsing. If he asked me back to his place, I knew I was going to nod my head and say yes.

But while I 'was' hoping he would ask me back to his place, I was also very nervous too, because although I'd been wearing women's clothes and living that life now for such a long time now, I hadn't actually ever had a real penis inside of me. Sure I had gone out with men, given the occasional BJ too (well.....not so occasional), but penetrative sex....never.

Yes, my bottom was quite used to the vibrator that I'd often slip inside of me of a night time while I masturbated in my bed. I had tried to train my butt even more by walking around for entire weekends with a 'very' large sized butt plug inserted inside of me, but while several guys I had dated had gotten some sort of oral sex from me, that was 'all' they got!

Oral sex didn't exactly trip my buttons and what I needed and dreamed of, was to experience a male penis entering me and giving me a long session of passionate sex.

Around 10.30, we had just finished another dance, when Greg whispered if I wanted to go home yet, or go back to his place for a nightcap before he took me home. My mind was already made up, so I looked up at him and gently said that we should go back to his house as I snuggled into his shoulder while he continued to hold me close.

Everything was falling into place, the flowers, the meal, the dancing. I knew he was aroused because his bulge pressing against my dress while we danced was very reassuring to me that he wanted to get into my panties.

There was 'no way' tonight that I was going to say 'no' or put up a struggle. All I wanted was for him to caress me, hold onto me, cover me in kisses and be gentle when he took my cherry. Oh please let him be slow, gentle and patient, I silently prayed.

We drove back to his house, with my hand very provocatively resting between his legs and I'd brush it very gently over the front of his pants occasionally, just to keep him aroused. We pulled up outside of his house and went inside where he proceeded to the kitchen and made coffee for us.

While he was in the kitchen, I seated myself on the lounge arranging my skirt so the overlap was sliding off my leg showing part of my suspender belt and stockings.

When Greg came in from the kitchen, his eyes were immediately drawn to the split in my skirt, as he handed me my coffee, trying to sit down without showing the prominent bulge in the front of his slacks.

As we finished our coffee, he stood up and put our cups on the side table before sitting back down very close to me.

He placed his arm around me and gently kissed my lips. In response to his kiss I moved my body around so he could put both arms around me while I kissed him back.

What started out as a tender kiss, found him gently probing open my lips and slipping his tongue inside of my mouth, while I reciprocated his every move? I leaned into him and he caressed the cheeks of my bottom in both hands, rubbing his hands over them.

My body had gone from a tense nervous block of granite to a quickly dissolving mass of jelly. I was not only jelly, but my passion was being quickly inflamed. The gentle kisses all over my neck and shoulders were turning me into a bitch on heat.

Once he realized he was kissing very sensitive erogenous zones on my body, and that I was now very pliant and submissively willing, he started to ease the zipper at the back of my dress downwards while my eager fingers were fumbling with his pants and shirt front.

All the while I was kissing his neck, shoulders and face while trying to fondle his dick, which was still inside of his pants.

All my pre-planned thoughts that I had previously decided on, for making this a slow, sensual search for my treasures, went out the door once he continued kissing my neck.

We both stood up, kissing and hugging trying to get undressed at the same time. He finally got my zipper down far enough so that I could shimmy out of my dress and his slacks were tangled in a heap around his feet and his shirt was completely unbuttoned.

In short order Greg was standing in front of me, naked and 'very' erect, while I was down to my bra, panties, suspenders and stockings.

With that, he simply picked me up, put me over his shoulders and carried me into the bedroom, with me giggling girlishly. His hands caressed my bottom, when he must have finally realized I was wearing crotchless panties and I felt a stray digit playing around the rim of my rosebud.

He gently eased me onto the bed and then leant down and got onto the bed beside me. I knew it was going to happen so as I was kissing his neck, I told him that I hadn't been all the way with a man before.

Suddenly, his whole being seemed to change. He paused in kissing me, looked deeply into my eyes and thanked me for giving him, my 'special' gift. He became determined to ensure I lost my 'cherry' in as gentle and womanly a way as possible.

We kissed and fondled for a while, with him slowly, but surely, easing my bra and suspenders off with the stockings bunching around my feet. I was fondling his cock, realizing that although it was not huge in length, it was certainly very thick AND hard.

Somehow I knew that 'now' was the time, so I slid off the bed and took off my panties and stood there before him. I keep my pubic area shaved smooth so he got to see everything, tiny penis and all.

I lowered my head slightly in a coyly submissive manner, thinking that almost every woman or girl reaches this point, where they willing submit their naked bodies to their lovers to allow them to take their virginity. THIS was 'my' moment.

In a quiet voice I said to Greg to be gentle with me. "But first, I want to do something for you" I whispered.

With that, I became completely and femininely submissive, dropping to my knees and gently placing the tip of his penis into my mouth and then I began to suck the tip of his cock further into my mouth, using my tongue to lap underneath.

"NO Nikki .... Tonight is for your pleasure," and I felt him gently slide his hands underneath my arms and gently ease me up to face him. He looked deeply into my eyes and I was completely helpless.

With that, he gently but firmly lifted me back onto the bed, asking me to turnaround and get on my hands and knees. He then placed both of his hands on my butt cheeks and slowly eased them apart and I was frozen in place, scared and frightened, when I felt him start to kiss my inner thighs moving up to my little crinkled hole, before his warm moist soft tongue started to push inside of me.

OMG! He's tonguing me I thought, silently thanking Cathy for telling me to thoroughly perfume douche myself, just incase things got heavy.

God forbid, but I moaned like a whore, while pushing back against his tongue. He continued to tongue and kiss my anus while I was meowing and whimpering, begging him to fuck me.

For some reason, a thought suddenly came into my head and I wondered if all women felt this way before having sex with a man for the first time. Me...I was nervous, excited, wanton, but scared if it was going to hurt, yet wanting it to happen too.

It was during these crazy, lust induced thoughts that Greg had stopped licking my anus and had reached over and gotten something out of his bedside table.

He leaned back onto the bed and I felt something cold and slippery touching my anus. He had coated his finger with some lube and he was rubbing it around the rim of my bottom.

Then he applied a little pressure to the hole and in popped his finger. It was sudden and it was a shock but it didn't seem to hurt me in any way. It was certainly a lot less thick than my favorite vibrator. Meanwhile he moved the finger round in circular motions, leaving me in a state of relaxed pleasure. Then he pulled it out and I was left with a feeling of being empty back there.

A moment later, his finger was back, pushing on my anal hole applying insistent pressure trying to burrow its way into me again.

"Relax," Greg soothingly whispered into my ear.

I did and the next thing I felt was a little resistance before 'two' fingers slipped back inside of me moving in a circular but more forceful pattern, trying to stretch me out. Then I felt further stretching and could now feel more fingers inside of me, stretching and prying me further apart.

Then.....I felt a jolt of electricity inside of me and dropped my head and elbows down onto the bed and let out a girlie little scream at the same time. I hadn't cum, BUT it felt like it.

"Its fun isn't it. You felt something like what a woman feels when she has an orgasm," Greg quietly laughed and told me that he had touched my prostate. - I 'knew' what he'd touched too.

My legs felt rubbery, and if this is what it was like with his fingers, what would it feel like with his penis. He still had two fingers in me and told me that he needed to stretch me a little more before he could fuck me with his dick.

'I' couldn't believe after using my butt plugs so often that he thought I was still tight!

As he continued to work his two fingers around inside of me, I felt his other hand rubbing around the cheeks of me butt. Then a firm insistent pressure on my hole and I suddenly felt that it was much fuller then before.

I realized then, that he now must have had fingers from both hands inside of me and judging by the pressure he was applying to my anal area was trying to force it further apart.

It was a little bit odd to know that I was being carefully pried apart, but it wasn't too bad, relaxing in some ways in fact.

Then he stopped all motion and I was actually humping back against his hands squirming and moaning in passion and desire.

When he pulled his fingers out, I cried out "NO....don't stop, please" and felt hollow and empty back there.

But he was stopping only to reapply more lubricant before slipping them back into me. I can recall becoming extremely aroused, whispering to him (actually it was pleading) to take me. I no longer cared or feared being penetrated; I just needed to have his penis inside of me. Then he eased the fingers from out of me,

I had my head down on my arms, thrusting my bottom back into thin air, panting and moaning, needing to fill the emptiness from when he had extracted his fingers.

I turned my head around and saw him rubbing lubricant thickly onto this dick. He saw me and smiled. The massaging inside of my anus had left me with a sexual desire and I was desperate to have him inside of me filling me up. I turned back around and looked pleadingly.

"Greg I begged, Wop it up my arse darling, please," I asked him.

"In a moment my little one," he replied.

Then he took his hand and placed it on my dick and tugged it till it was erect. He then got off the bed and came round to face me directly.

"You're ready now, so get back up onto your hands and knees for me darling. In a few moments you'll feel like you're in heaven!"

I felt the bed sag and his hands grab my hips, gently but firmly. I started to feel something stiff push against my opening and then felt him ease a little bit closer and grab my hips even harder.

I could feel an insistent pushing against my hole and it was starting to hurt a little.

"Relax your body and strain like your going to the toilet" Greg quietly urged me.

And with that I strained very hard and suddenly felt something very big squeeze into me. I was gasping, as was Greg.

I couldn't move and was scared and it felt like he was going to split me apart.

It felt like someone had stuffed a tennis ball inside of me, except I felt stretched and very full inside. But I knew it was just the 'head' of his penis. All the while Geoff was quietly talking to me in a quiet soothing voice.

"Relax, I won't push any further into you until you tell me it's OK to. I won't hurt you darling," Greg comfortingly told me.

That's what 'he' says I thought to myself. But it wasn't his bottom that had something in it I thought, that was the size of a large post and I was definitely nervous about what it would do to me, if he shoved the rest of it into me.

After a few minutes I felt the fullness back there become more comfortable, and gently tried to push back saying to Greg, that it's was very big but I didn't feel anymore pain.

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