A Journey with Emily Pt. 02

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A young man's discovery of a deviant life.
7.9k words
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Part 2 of the 2 part series

Updated 10/01/2022
Created 09/21/2011
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kanda42
kanda42
4 Followers

Chapter Three

I slowly came to on the Saturday and realised I was alone. I had slept really well and so guessed that my fuck buddies had finally spent the night in their own bed.

As I laid on my bed I heard Emily downstairs. She was humming loudly and making her usual noise in the kitchen. I needed to go to the bathroom, so I threw on my Ralph Lauren pyjama bottoms and a tee shirt and headed out the room. I noticed Emily's door was open and peered through, secretly wondering if Jamie was there, but he was not. I noticed her bed had no sheets again.

I went downstairs and into the kitchen. Emily was cheerily getting some fruit as she heard me enter.

"morning " she beamed. "sleep well?"

"yes, thanks" I replied. " I think so"

Emily laughed. "Jamie and I nearly came in but you were out cold and you looked so peaceful. Jamie also had to leave early to get back to London as he had to go to work this afternoon. He told me to give you this" and she kissed me on the lips.

Once she finished, then whispered "and I want to give you this" and kissed me again, this time her tongue and mine entwined.

Emily then said that we had loads to do. First though she said we needed breakfast. Emily commented that as it was a nice day and it was only us in the house we ought to complete our chores naked.

With that she removed her bath robe. I needed no encouragement and removed my clothes. Free at last.

We ate breakfast and then went to work on the house. Emily had washed her bed linen as she again had leaked sperm over them. We took the sheets into the garden to dry, completely oblivious to the fact we were naked. As we put them on the washing line to dry, Emily patted and lightly stroked my cock, stating that it gave her ass a really good session and she enjoyed feeling my sperm dribble from her bum for most of the night.

After an hour or so we were sorted. We sat and had a coffee. And a very long chat.

Emily said that she had pretty much planned the whole thing but was worried it might not go to plan. Jamie had been speaking to her about threesomes for ages, and she was reluctant at first but Emily, being deviant, turned the tables and said to Jamie that she would participate but it would have to be two guys. Both of them had been looking for a while for a suitable candidate but they never found anyone. Even during our late night chats walking back it never occurred to her that I may be the one. It was only when Emily went to London and met Jamie and confessed about our encounter that it dawned on her that the ideal candidate slept in the room next door to her.

Emily initially thought it would be a really hard to organise and that I may be reticent, but the whole thing clicked and blew her mind. Jamie and her were drifting apart and Emily knew this maybe the last time they were together, so she wanted it to be a time to remember. Emily said it was defintately the best sex she ever had, and watching Jamie and I together was utterly amazing and had really turned her on. So much so that she aksed would I be willing to be her occasional fuck buddy?

I agreed. It was a perfect arrangement.

Emily however said I could do her a huge favour and teach her how to suck cock. Jamie apparently said that I was the best by miles. Emily said that it was the horniest thing she had ever witnessed and that she wanted to be as good as me.

Emily asked how I felt about having a bisexual encounter. I said that it was the right time, place and person and it was really special. I added that the cum volume was a bit of a shock, but sucking it was easier than I thought, and the taste was not unpleasant upon swallowing. I told Emily that I was really pleased I had made Jamie cum, as he was my first one. Feeling him unload was a real turn on as Jamie must have enjoyed it too. I was actually rather proud! I agreed to do it again, but I was not sure about getting fucked in my ass just yet.

"Good" she said "because I want two bi guys again but you should let me fuck your ass though, as you have had mine. It may not be the Jamie next time. I also promise that I will try sex with a girl and if she's interested, see if she wants you as well. "

What more could I want.

We noticed the time and that one of the other housemates was due back. All the beds were made and we had managed to mask the lingering odour of sexual intercourse throughout the house.

We reluctantly got dressed.

I said I would arrange a lesson for Emily.

Chapter 4 : Lessons start

Emily was true to her word and never mentioned our liaison to any outsider. I guess she did not want anyone knowing that she had been fucked by both her boyfriend and me, and after she had watched me orally drain him!

Our other flat mates were back from their weekends away, and all our lives returned to normal. The mundane week started and Emily and I carried on as normal. Jamie had called on the phone a couple of times but it was pretty clear that their relationship had reached the end of the road. Emily was a little sad to start with, but she knew it was the right thing. I had decided that I would leave her some space before I reminded her that she had some lessons.

After two weeks or so I was at home on a very dull afternoon when I decided she needed a lesson. Emily was out. I placed a note under her door which simply said "lesson 1 -10pm"

The four of us who shared the house always congregated around supper time at about 730pm and we hung out together until bedtime, unless we were going out. Emily never said anything about the note and all four of us sat and ate and watched rubbish television; our usual routine.

I went to do some work at about 930pm in my own room and guessed Emily would duck out of the little challenge of the lesson that I had suggested.

10pm came and went and Emily did not appear. I assumed she was apprehensive as our flatmates were downstairs, which was understandable.

At 1020pm and there was a tap on the door. In walked Emily quickly, shutting the door behind her

I was sat at the desk.

"sorry I am bit late" she whispered "it took ages to get all this stuff on and Stephanie kept talking to me"

I frowned as she was wearing pyjamas and slippers. Emily laughed.

"Not this you idiot - I put this lot on so I could get from the bathroom without anyone wondering what the fucks going on."

Emily then took her pyjamas off to reveal underneath a beautiful black basque with vivid fuscia lacework, suspenders holding up black lace topped stockings, with tiny pink bows at the back, and a delicate lace g string.

"wow" I gasped "you look stunning"

She turned around showing herself off and boy did I want her.

I would have been happy just to look all night, but no she said, she wanted her lesson and removed my shorts freeing my cock and balls.

She bobbed down in front of me holding my erect member, and said "Right what shall I do?"

I told her how what parts of oral sex really worked for me. I taught her how to go around the inside of the foreskin with her tongue, use lots of eye contact and to say dirty comments. I told her to say how nice the cum tasted, that it was a big cock and that she loved sucking cocks. I told her to mix it all up, and to basically treat it carefully and make love to it, be slow, then a bit faster and look like you're in love with it and then act like a whore.

I gave her a guided tour in a sense, pointing out where to stroke and lick, reminding her not to forget ass play, as I really liked mine being stroked whilst sucked. I taught her about sensing an orgasm was close and how to masturbate and make the cum shoot from the cock.

Emily wanted me to come like Jamie had with me, so I talked her through how to hold and what to expect and how to anticipate an orgasm. I told her for a guy, its really hot for you to show your mouth full of cum before you swallow, or to have it splash on your face.

Emily said she wanted to taste, so I masturbated really close to her open mouth and dutifully obliged and shot my load in her mouth. Like a good girl she showed me her cum filled mouth and swallowed.

"That was yum" said my pupil as she swallowed my warm load. "I think that's the first time I have tasted your cock properly. It's nice and not too salty either"

I said to Emily that she was amazing and that was the best blow job I had ever received. She was very proud. We curled up on the bed and I stroked her hair. Her ass looked amazing in the basque and I told her so. It made her look exquisite and special.

"Thanks" she said " I don't normally wear this sort of stuff, but I was given this a while back and have not worn it yet. I wanted to try it out on you first"

"Well it works a treat" I added.

Emily said she ought to get back to her room quietly.

As she got up, she glanced in the mirror and noticed how lovely she looked.

"I may wear this Saturday night" she announced.

"Are you going out then?" I enquired

"Only to see Jane, my friend from class at her flat. She has promised to cook supper" said Em, still admiring herself in the mirror.

"That will be nice. Is she the one with the food allergies? What do you reckon you will eat then?" I enquired innocently.

Emily turned and looked directly at me. There was a long pause before she quietly said

"Errmm I imagine it will be pussy. It's just me and her for dinner. I think she wants to fuck me."

Startled I asked if she would

"Of course; she's attractive, intelligent and I imagine good in bed. You really enjoyed your little bi journey and I want to have a one too. If we do fuck, I promise I will tell you if she says I can, and I may see if she wants to join our little club"

She winked , got dressed back into her pyjamas and kissed me goodnight.

Chapter 5

Over the next few days I sensed Emily's growing excitement. All four of us went out as usual on Thursday and had a very boozy evening with our respective friends. Emily and I ended up meeting in the club, and left at about 1am. We had an agreement that if we were both alone at the end of a night we would walk back together.

I noticed Emily at the exit "You going home?" I enquired.

She nodded and we set off. On the way back I joked and said I was surprised that she had not managed to find a sexual partner for both of us that night. She giggled and said that she was on a no sex diet until the weekend.

"Oh that's nice,so my blow job does not count?" I grumbled.

"Don't be daft. That's part of the build up. It made me horny and now I really really need to masturbate, but I am not going to, so that by the time I see Jane on Saturday I am desperate for sex"

Emily mentioned that she was almost certain that Jane wanted to fuck her. Emily guessed Jane may be interested, as they had been doing some college work when an issue arose about how to resolve a gay or lesbian employee issue, and Jane said to Emily "if she's as pretty as you I would resolve it in the bedroom "

Emily had also mentioned to Jane about her decision to break with Jamie, and Jane had said if she ever needed anything all she had to do was ask, and had delicately kissed her cheek and seductively whispered "and I mean anything", and had gently patted her arse.

We got home and Emily went to bed.

The next evening Emily and I went for a quick drink together in the local pub.

The couple from two weeks ago who Emily flashed were there and said hello. I bought a drink and we sat down. Emily said she was really nervous about the following evening as she did not know what to expect. I told her not to plan anything just do what happens naturally. Don't expect anything to happen. I also said that if she wanted to mention our little experiment she could, but don't push it.

As we left the lady from the couple said "Bye".

I waved and Emily winked and said "possibly tomorrow evening" and laughed.

Saturday arrived.

I had been out most of the day playing sport, but hurriedly got back at 6pm. Emily was due at Janes' flat for 8pm, but luckily it was just a short distance from where we lived.

Music was blasting from her room. I went up and knocked at her door.

"Its me"

"Thank fuck" came the reply "Come in. I need help"

I stepped into chaos. Most of her wardrobe was on the bed. She had no idea what to wear, and was getting stressed out. She wanted to strike the right balance between pretty,sexy and fuckable, and was struggling to find something suitable.

"Has to be a skirt or dress and decent underwear. You can't turn up without wearing any knickers" I said.

"Let me sort your underwear and you get on with dresses"

"Its too warm for the basque so that's out" Emily said. "don't want to arrive sweating. Have a look and find something quickly"

I had a pleasant few minutes rummaging through her underwear drawer when bingo right at the back was a brand new set. Black and dark blue delicate lace suspender, bra and knickers. It was a deep vintage style suspender too, so it would be comfortable and also wearable during sex. Her arse would look lovely as the knickers and had a pretty pattern at the back which matched the detail on the suspender. Perfect. And I found some plain black lace top stockings.

Emily was now naked, and the midst of trying on dresses. Eventually she got it right and had found a simple strappy dress, a pretty dark blue and white floral number, just above the knee so not too short or tarty. She also added a simple plain knitted cardigan.

"Thanks" she said and kissed me "time for a bath"

"Don't forget to shave" I said pointing at her pussy "Jane will want to taste you and your cute arse so do a thorough job. I will tidy up your room"

It was intensely erotic for me helping Emily have her first lesbian experience. I was really hoping it was a success.

Emily came back and the room filled with a delicate scent of mandarin and jasmine.

"That's a lovely aroma" I said

Emily dropped her robe and showed me her shaved pubis asking me if it looked ok. She had shaved a lot closer that I had seen before and retained a tiny landing strip. She was completely shaven around the entrance to allow Jane unfettered access to her lips and little rose bud clitoris, should the need arise. I did lie and tell her that she had missed some hairs around her arsehole, and Jane may be put off , so I got to have a turn and shaved the entrance to her ass. Emily had a stunning bottom, with pert buttocks.

She dried her hair and put on her make up and I then helped her into her underwear. I adjusted the bra, so her boobs were lifted up and gently pushed together as she wanted to make an impression. Emily had wanted to wear the underwear properly, so the suspender went over her knickers so she had a perfect contour. I fastened the last front suspender to her stockings, and noticed the distinct odour of a sexually excited woman. I said she looked drop dead gorgeous and that if Jane did not fuck her then I would.

I helped her into her dress and she looked in the mirror and was really pleased. Emily had deliberately chosen a dress that buttoned up at the front, so she could slip it off elegantly, revealing her lingerie if she wanted.

I patted her perfect arse, and asked if she had everything she needed.

"Yep" she said opening her bag "Keys, money, cards lippy, knickers and dildo"

"ha ha" I said.

Emily opened her bag and showed me an exquisite glass dildo with gorgeous coloured ribbed sections.

"I hope you really enjoy yourself" I smiled.

She walked downstairs and spoke to Lynn and Stephanie.

I came down and the three girls were in deep conversation, mainly quizzing Emily about where she was off to. Lynn and Steph were both teasing her saying that she must be meeting a man, as she had made a real effort and looked really pretty. Emily firmly said that she was going to see Jane and that was all.

The two girls asked my view about where Emily was going.

"Sefinitely a man involved" I said "do you want us to wait up in case you bring him back?" I teased.

"Fuck off" Emily joked. Lynn and Steph said that would want to know all about him. Emily said she had to go, and said a cheery "see you all later"

A little later Steph said she was going to meet some of her mates in the same bar that I was heading to, so we got ready and set off.

Steph on the way said she was sure Emily was meeting a man. I asked how so sure and Steph giggled and said as Emily left to go out, Steph was fairly certain Emily was wearing stockings.

"Really?. I never noticed" I added.

Chapter 6:

I awoke on Sunday, headed downstairs for a coffee and was quite surprised to see that Emily's room was dark. I then remembered that when I got back late last night, she was at home, as her door was firmly shut.

I hoped that the previous night had not been a disaster.

I made coffee and headed back to my room. Emily must have heard as she shouted out "white no sugar please"

I headed back downstairs dutifully and made her a coffee. I knocked lightly on the door and went in.

"Good Morning Emily. Surprised you came back ; how was last night?" I asked.

"I cant tell you now with the others about,you nosey deviant. I will tell you later when out the way of the other two. How about you meet me after work at 7 tonight and buy me a drink?"

Stephanie was now up, so I slipped discretely from her room.

The girls did the usual tease of her, and Emily left for work. She said she would be back really late to them as she had a full double shift, but on the way out mouthed "meet you at 7"

The day dragged for me. I watched the clock virtually every hour as I waited for the time to come so I could meet Emily and find all about her experience. I really hoped that she had an amazing time but also was concerned in case it was a disaster, as she had come back home after all

I met Emily and was a little early, so I had a drink and bought her one as she neared the end of her shift. She said she needed it!

Emily was clearly really excited we left her place of work. I did not need to even ask as the first things from her lips were

"Jane said I can let you know of our evening"

"Brilliant. Tell me all the detail you deviant girl"

We walked to the local bar with our arms wrapped around each other.

I bought a bottle of wine and sat down and Emily began to tell her tale.

As Emily set off from our house she was seriously turned on, but as she headed closer to Janes she began to get really nervous about what journey she was embarking upon. She felt a heady mix of extreme excitement and nerves, which was strangely enjoyable. She was in danger of turning back but luckily she arrived at the entrance to the flat.

Emily said she took great comfort in the fact that I had never had a same sex encounter before Jamie, but he claimed that I had given him an amazing blow job, probably the best he had, so she thought it can't be that tough to fuck someone of the same sex. She had a few deep breaths and managed to control her breathing and then opened the communal door.

Emily walked up to the second floor and resolved her inner turmoil by thinking "I am simply going to a friends for supper – nothing else"

She got to the door, took a couple of deep breaths and with a slightly trembling hand rang the doorbell. Her stomach tightened as she heard foorsteps behind the door. The latch was turned. Too late she thought and swallowed hard.

Emily was rather shocked when the door was answered by another lady, who she had never met.

Thinking she had the wrong apartment, Emily immediately apologised but the lady laughed:

"Hi – you must be Emily. Come in, please. Jane is still getting ready. I am Helen. Come in and make yourself at home. By the way you smell gorgeous and look pretty – love your dress"

Emily went in. She was apprehensive as she thought that it would be just her and Jane.

kanda42
kanda42
4 Followers