My Life Changing Night (part one)

This is the first story in what may become a series of confessions and true stories about how I became the 39 year old woman I am. It happened in 1991 and is all true, the dialogue may be a little inaccurate but it's to the best of my memory.

I should explain a little about me to set up a bit of a back story: When I left school I was overweight and had been for most of my teenage life. Also (for reasons I won't go into) I had to look after my Mum a lot of the time, so I left school with next to no friends, no social life and a bit of a belly. I was shy by nature and was happy to sink into the background within my first job as a trainee legal secretary. Probably because I wasn't into small talk or socializing, I was seen as studious and determined and I excelled at work and within a couple of years I was working as a fully trained legal secretary for one of the senior partners, Jennifer. I had also lost weight but kept my ample size breasts, but still at eighteen years of age, I'd still not been kissed or anything beyond that.

These events happened the week after my eighteenth birthday, which I had not celebrated or made known at work. I had been helping Jennifer prepare for an important meeting in Derby, which is a good few hours drive from where we were based, so because the meeting was at 2pm, Jennifer had booked us both a hotel room each for the Friday night. This was not unusual, I had been away with Jennifer before, but would normally spend the day sat in the lobby in case I was called upon, this was the first time we would be returning at the weekend.

After Jennifer's meeting, which I had not been called upon to assist with, she came to find me and asked me to join her for a drink in the bar. This was rare because normally she had a meal with the clients but being a Friday afternoon, they had left for the journey home. It was just before 5pm and Jennifer told me that we could leave if I wanted to but she would much prefer to open a bottle of wine and return the following morning if I had no plans. I never had any plans so was happy to stay.

We moved to the bar and Jennifer ordered a bottle of champagne.

"Champagne" I asked, "the meeting went well then?"

"The meeting went very well" Jennifer replied, "but the Champage is to celebrate your eighteenth birthday last week"

"How did you know that", I exclaimed, "I never told anyone".

Jennifer explained that she had made a point of noting each of her secretaries birthdays on her computer and had been annoyed with herself for being too consumed with this meeting to not get me anything. I told her not to worry, I'm not really one to celebrate my birthday anyway.

"Didn't anyone make it special for you, then?" Jennifer asked.

"I don't really know too many people, to be honest" I answered.

"You must have a boyfriend surely, a young girl like you" she asked.

"No" I answered, looking slightly embarrassed.

"A girlfriend then?" she asked.

"No, nothing like that" I answered, rather too quickly, "I've just never met anyone"

"NEVER met anyone, really?, NEVER met anyone, at eighteen?" She asked, seemingly surprised.

"Eighteen and never been kissed" I told her and immediately drank down my flute of champagne that the waiter had poured me, rather ashamed at blurting out such a confession.

"Goodness" said Jennifer and refilled my drink and toasted my birthday. We chinked glasses and I drank my second glass. I don't drink but it would be a lie to say that I was drunk. I was light headed but still had all my senses about me.

"Why don't we make a nice evening of this?" Jennifer asked, "let's drink too much and wake up late morning and get home late afternoon? What do you say"

I nodded, "why not, I've never been drunk" I answered, which was true.

"There's so much you've not done Deborah, believe me" Jennifer told me.

Jennifer said that we should get changed and come back down to the restaurant. As we were walking up the stairs, having already shared a bottle of champagne, she asked me to bring my stuff to her room and we'll get changed together. "We'll put some music on, I'll get another bottle sent up to the room, it'll be like having a girls night out" she told me. I agreed, I'd not unpacked, so I got my overnight bag and made my way to her room.

When I got to Jennifer's room, room service were there delivering the champagne and Jennifer immediately poured me another glass. She spoke to me about the meeting that day and complimented me on the job I was doing and as she spoke, she undressed down to her bra and knickers and got herself a robe. I was rather overwhelmed with her confidence and didn't want to appear like some prudish young girl, so I did my best to join in the conversation.

"Why don't you have a shower first" she asked me, "I need to make a couple of calls anyway. "I'll get in after you" she said. I agreed and went into the bathroom to change.

"Leave the door Deborah" Jennifer called after me, "I need to get my wash bag when I'm done here".

I left the door open and got undressed in the corner away from the view of Jennifer. I wrapped a towel around me and went back into the bedroom to put my clothes on the bed. Jennifer was talking work on the phone and smiled at me as I walked back into the room.

I went back into the bathroom and hanging the towel back up, I entered the shower cubicle and turned it on. Within a few minutes, steam rose from the cubicle thankfully steaming up the glass, which I remember being very pleased about in case Jennifer came in for her wash bag.

I'd been in the shower for only a couple of minutes before I was jumping with surprise as I felt a cold draft on my back as the shower door was opened, I'm sure I almost screamed as Jennifer stood there. "Sorry Deborah, didn't mean to make you jump, I've got something here for you to use" Jennifer had her robe on but she said "hang on" and she closed the door before immediately opening again to reveal her naked body in front of me.

"Move over, I'll do it for you" Jennifer told me, I had my back to her and my arms across my chest. Jennifer showed me her hand to reveal one of those natural sponges and in the other hand a fancy looking bottle, which she squeezed onto the sponge and put on the shelf.

"It'll be easier of I just do it for you" Jennifer said as she then began rubbing the sponge over my back and telling me how she uses it every morning and night and it removes all the dead skin and other beauty regime small talk.

She didn't seem to think it was strange that we were both naked in the shower and her talking so calmly about gels and oils did relax me and the sponge did feel nice. Jennifer made her way lower towards my bum and I remember her commenting on how good my skin was and how she spent hundreds of pounds on cosmetics to help her stay young looking. As the sponge brushed over my arse I felt a tingling between my legs. Jennifer didn't spend any longer on my bum than she did on my back and she quickly began rubbing the back of my legs.

"Turn around" she told me. As I did I was faced with Jennifer standing naked in front of me and desperate as I was trying not to look, I could see her breasts which were smaller than mine but her nipples stood erect and I could see her neatly trimmed bush between her legs. I felt ugly stood next to her, it's true I was slimmer now, but I still had little self esteem and my bigger breasts made me feel fat and my hairy bush made me feel dirty and unhygienic.

Jennifer seemed to take no notice of my nudity and began rubbing the sponge over my neck. She did compliment me on my breasts and told me she would love bigger "tits", her crude language making me excited but also making me blush. I laughed politely not wanting to show how embarrassed I was and not wanting to say anything that made me sound like a stupid little girl. My nipples hardened and tingled as Jennifer rubbed the sponge over them and as Jennifer made her way towards me stomach, I distinctly remember her saying "lovely".

I was becoming aroused and alarmed that Jennifer was making her way towards my pussy (I didn't even have a name for it then!) I was worried she wouldbe able tell that I was turned on when the put the sponge over it and that she'd think I was dirty or that I was letting her down when she was being nice to me. I know that sounds stupid but with my age and lack of experience I had no idea I was being seduced!

Jennifer went from my stomach to my left leg and worked the sponge down towards me foot, I breathed sigh of relief. She then went onto my right foot and worked her way up my right leg. I froze and then realised that Jennifer had stopped washing me. I looked down and Jennifer was knelt down in front of me with the sponge in her hands looking back up at me.

We exchanged a look, a look I can't explain, but I felt that Jennifer was asking me permission to touch me there, I didn't want to say anything and I didn't want to nod so I didn't do anything. Jennifer carried on looking at me as she brought the sponge between my legs and I think when she could see she wasn't getting any refusal from me, she put her head down and stared straight at my pussy as she worked the sponge around it.

Even with the shower humming above me, I could still hear my breathing becoming heavy but even now, I still didn't know if I was misreading the situation and I didn't want to moan loudly in case I offended Jennifer. This changed however, when Jennifer brought her other hand up behind me to my bum and began squeezing my arse pulling me towards her other hand. I groaned loudly and when I felt Jennifer's fingers rubbing my clit, I looked down to see she had given up with the sponge.

"Oh god" I said loudly as Jennifer lifted my left leg over her shoulder and buried her head in my wet cunt. Her other hand was rubbing the base of my cunt from behind as a tongue entered me for the first time ever. I was grinding my pussy against her mouth and knew I was close to cumming.

Jennifer moved her head away and rubbed my clit with her fingers as the other hand fingered me from behind. I lifted my leg up higher to give her more access and I remember I just kept saying "Oh God, Oh God" as I began to reach my first ever orgasm with someone else.

Jennifer began rubbing her thumb over my arsehole as her fingers remained inside my pussy, her other hand rubbing my clit. When her thumb entered my arse this pushed me over the edge and it was at this moment I knew I loved fingers in my arse, something I knew nothing about up until now.

The orgasm very nearly took me off my feet and without Jennifer supporting my leg, I think I would have just collapsed to the floor. It was the most incredible thing that had ever happened to me. My whole body shook and I felt it was never going to end. Jennifer kissed and licked my pussy until the euphoria eventually faded.

Jennifer got to her feet and kissed me, again the first time I had even been kissed in passion. She told me to get dried and dressed. We were going down to dinner and the night was only just beginning and my God, how right she was.