Sissy Diary... Becoming a Sissy

There are some life experiences that define when a person truly becomes a true sissy.

The following story was one of those defining moments in my developing sissy life.

When l was just 21 years old l met a lovely 19 year old girl called Sue and we fell in love. I asked her to move in with me after dating for a couple of months. She agreed to live with me and we were very happy for a while. Sex was good to begin with and she seemed content to enjoy our initial love making, even though my little undersized cock didn't making her cum. More often than not Sue preferred to give me a quick blowjob, while she demanded I ate her pussy.

Sue wasn't very sexually experienced, telling me she'd only ever had a few guys before me. She was reluctant to say more about her previous sexual experiences. I once asked if any of her ex boyfriends made her cum but she refused to answer and would argue not all women cum through penetration.

Later I found out she liked to have an orgasm, using her own masturbatory methods. This didn't worry me as I would jerk off whenever I felt the urge, even in the middle of the night lying next to her sleeping. I would use only one finger to jerk off like a girl fingering her clitoris. The situation of satisfying Sue did become more worrying as l tried my best to please her in bed. My premature ejaculations didn't help either to give her any sexual pleasure.

Things began to change quite quickly in our relationship when one evening I received a facebook message from Steve, an old college friend, who I'd not heard from for nearly two years. We'd lost contact after he'd got married but said he was currently involved in a messy divorce.

Steve was a good looking, six feet tall, dark haired guy. When at college he was always bragging about how many girls he'd had in bed. The girls would often want him as a trophy due to him being so "well hung".

As he was now free and single he wanted to check me out and revive our friendship. He knew l'd bisexual tendencies. Once in a drunken night out I even offered to give him a blowjob. He turned me down and laughed at the idea, saying i wouldn't be able to handle his big cock. After seeing him naked in the changing rooms at the college gym he wasn't lying about his size. Steve always kept himself very fit and loved bike riding. He knew l liked bike riding too. So he insisted we meet up one weekend and go on a long bike ride together.

Sue, my girlfriend, had never met Steve so l was a bit worried they wouldn't get on with Steve as he could be brash and overconfident. The weekend that Steve came to my home was the turning point in my relationship with Sue. He arrived at midday, the weather was very warm and sunny. I answered the door and he stood tall wearing bright red and yellow cycle gear. Steve had bought the whole lycra bike kit which showed a huge bulge in his pants. I couldn't help immediately noticing that his cock lay across his right thigh like a thick 5" sausage.

"Hi how's it with you bud? Do you like my new gear?"

"Sure, you look the part mate" I replied.

He followed me into the living room where Sue was sitting on the sofa. I introduced Steve to her and she stood up and awkwardly held out her hand, which he took and cheekily kissed it! She actually blushed and I noticed her eyes stray towards Steve's groin area and she actually licked her lips as she gazed at his large member! I know women often say size doesn't matter but that's bull. She was almost salivating as she sat back down. Steve sat next to her with his legs wide open and hands behind his head. His body language said it all, that he was in charge and Sue was well impressed.

I went into the kitchen to make some cold drinks. I could hear Sue giggling at Steve's chat up lines and by the time I returned to give them the refreshments Steve had moved closer to Sue with his hand on Sue's arm.

"So where shall we go for a ride Steve?" I asked.

"Oh, anywhere you like. How about the Lake which is 25 miles there and back? Are you coming with us Sue?"

"No thanks I don't ride".

"Oh, I bet you do Sue. I bet you do!"

Sue blushed again as Steve ran his fingers down her arm teasing her as she looked down at his bulge with her eyes fixed to his cock. I left the room to get changed into my bike gear. I'd bought some awful padded lycra shorts and a tight t-shirt. I stood in the full length mirror at myself and I thought l looked stupid at my small bulge which was hardly noticeable compared to Steve's big package.

I really didn't want to go downstairs to embarrass myself in front of Steve and Sue but had no choice. They were having a good laugh at one of Steve's bad jokes when I said it was time to go. Steve looked me up and down and sort of sniggered. Then he stood up tall next to me and said:

"Who looks the best rider to you Sue...Me or your little lad?"

Sue being diplomatic replied we were both super fit and as she stood up she squeezed Steve's arm and walked out of the room in a sassy sort of way women do. I felt she was turned on by Steve and while we were on our long bike ride I couldn't help thinking, "l bet right now she's fantasizing about being fucked by my old college pal". This thought kept running around through my mind all the rest of the day, as we cycled over the hills and valleys to the Lake.

Steve couldn't stop talking about how lucky I was to have such a sexy woman like Sue in my life. His marriage was a major disaster as many of his relationships with women had generally been. If he had a nice easy going woman like Sue, who understood his needs and desires he said he'd be really happy. I said it's not easy to find a live with partner who was completely compatible, as there were always some things that weren't fully satisfactory.

"You mean your sex life isn't so great? asked Steve.

"Well...sort of... err not at the moment...not really".

"How's that then...you can't fulfil her with your small package?" Steve chuckled.

I didn't reply but looked over the Lake at the swans. After we finished our snack we got on our bikes and rode back over the hills to return home. We parted at the nearby crossroads and Steve went back to his flat in town and I went back to my home. When I got home Sue asked me a dozen and more questions about the ride, interspersed with questions about Steve. She wanted to know more about his past, where he lived and how long he was married. I could see she was impressed with Steve, especially his fit physique and confident manner.

"Are you seeing Steve again for another ride out?" Sue enquired.

"We've not arranged another time. I expect he's going to be very busy chasing skirts, as he said he was horny as hell and wanted to make up for lost time after being in a fixed, messed up marriage these past few years."

"Oh I see" said Sue looking a bit disappointed.

I added: "Maybe I should go and visit Steve one evening at his flat to see if he's not getting too depressed because of his break up?"

Sue thought that was a bad idea and he might see it was prying into Steve's private life. Sue later asked me again where Steve lived in the town, so I told her I'd kept it in my address book along with his phone number. She seemed to smile when I said that as though it logged in her mind to consider her own future options. I realised later it didn't take long for her options to become a reality as her demeanor and normal habits began to change over the coming weeks and then I suspected my girlfriend was having an affair with my pal Steve.

The signs of Sue's infidelity were made clear when she began to buy and dress up in new outfits. Not coming home at the usual time after work and especially at weekends on her long shopping trips. When she came home from being with Steve I could smell the sex emitting from her body and Steve's testosterone sweat coming from her clothes.

She would quickly would go and shower and change her clothes and throw her underwear in the washing machine to wash later on. I began to be obsessed with taking her panties from out of the washing machine to see if they were stained with cum. They were always semi wet with stains as l put the crotch to my nose and lips to taste a sweet mix of her wetness and Steve's cum!

I felt like a pervert as l tasted her damp knickers, My clitty got hard as l thought of her traveling back home with Steve's cum still leaking out of her wet pussy. The second time l took her wet cum stained panties from the washing machine l couldn't stop myself jerking off with them wrapped round my dick. it was such a fucking thrill!

Sue's infidelity was most obvious when she refused to have any kind of sex with me. Made up excuses that she was "tired" and getting constant "headaches" from stress related work.

Steve didn't contact me to arrange another bike ride, so I sent him a facebook message. He replied a few days later that his bike needed an overall fixing, adding he was having problems sorting out his divorce proceedings. Of course l didn't believe him. So l decided that when Sue was going on one of her long shopping trips on a Saturday, I would go to Steve's flat a short while after she left home and hope to catch them at it.

Steve lived in a 50's style block of flats with communal stairways that were easily accessible. I'd been to his flat a couple of years ago to collect some software and a printer. I remembered his flat was very small with a sitting living room with a double bed and only a couple of chairs and a cupboard. The kitchen and shower room were also very small.

I gave my girlfriend plenty of time to get to Steve's flat, as l suspected she'd be there for at least a couple of hours before going shopping to cover her tracks. Steve's flat was situated on the second floor and his front door was facing the back of the building. I knew the front door went straight into his bedsit living room so I would hear any noises if l stood near the door.

It was just after 1pm when I got to Steve's flat and boy was I nervous as my heart was beating fast. I stood outside his front door and tried to listen to any voices coming from inside. It was very quiet except for some music playing in the background. Then I heard his voice talking to someone and saying how much he liked the music. Then it went quiet before I heard a woman's voice but it didn't sound like Sue's voice until she laughed. Then I knew it was my girlfriend inside Steve's flat. It went quiet again before I heard her giggling and soon began to start making a constant moaning.

I so wanted to open the letterbox to peek inside but I thought they might hear it creak open. I felt a weird mix of envy, anger and sexual arousal as I stood helpless knowing my girlfriend was being fucked by Steve my old college buddy! Her groaning and moaning got louder and louder as she called out his name several times. Sue never made such erotic noises like this when we made love...not ever!

My cock got involuntary erect and I felt so horny and ashamed I was feeling like this. Then a voice called out from along the stairway:

"Hello...are you wanting someone? Can I help?"

I saw a small guy in his late 30s standing at the next door flat with a glass of wine in his hand.

"It's ok, thanks. I came to visit my friend Steve but l see he's busy, so I'd better not disturb."

"Steve? Yes he sounds like he's got company. I can hear them through my adjoining walls. They're paper thin you know. Hey, so while you're be waiting, why not join me in a glass".

I thanked the guy and asked when he thought Steve would finish his business (of fucking my girlfriend). His neighbour said if it's the girl he'd been seeing recently then probably in another hour or so. I thought I'd better join the guy and accept his offer of a glass of wine and at the same time listen to the couple from his flat, instead of hanging outside like a weirdo. The guy was very friendly and his name was Francis and said he was half Italian. He'd only been living in the flat for the past year but didn't really know Steve that well.

Once in Francis's flat I could hear Sue moaning and groaning even more clearer through the adjoining living room wall and the constant rhythmic banging of the bedstead. Steve was thrusting his huge 8" plus cock in my girlfriend's pussy!

"Steve's really going at it today, isn't he? Most girls he screws of late just can't get enough of him. It won't be longer before she'll start making those orgasmic noises girls love to make" said Francis breaking out in laughter.

"How about you...what's your poison?"

"I'm straight but have known to stray in the past" l replied.

"Really? That sounds interesting. How about now?...is the sound of them fucking turning you on?"

"Sort of...It's been going on for ages...doesn't he ever stop?"

"Not before she cums, l guess, but then the guy seems he can recover in no time for second helpings!"

When Francis said that l felt from that moment l lost my girlfriend for good. And found myself laying back on Francisco's bed listening to her sensuous lusty moans at every deep cock thrust.

Before I knew it Francis climbed all over me and we began kissing and stripping off our clothes. He fucked me for the next hour and it was amazing, I completely forgot about the couple next door as Francis took charge and made me cum. I heard Sue's voice after a while and then a door slam shut. I peered out the window, down on the street and there walked my girlfriend Sue with a big smile on her face and arms swaying like she was the happiest girl alive! She looked up at Steve's window and blew him a kiss!

Francis lay naked on his bed and asked if I wanted to go and see Steve now he was free but I said it was ok another time and I lay my head on his chest and continued to stroke his gay cock. Later when dressed he asked if I wanted to visit him again and I said of course. But I asked Francis not to say anything to Steve about my visit. I thought the day had turned out to be stranger than I could ever of imagined as I passed Steve's door. I felt sort of liberated from the anxiety I'd previously felt and didn't care that my girlfriend was screwing my old pal.

When I arrived home I showered and changed before Sue got back. She looked sexy and radiant and I guessed it was because the sex with Steve was to her complete satisfaction that made her more happy and content than any other time I'd known her. A few days later I went back to see Francis at his flat knowing Steve wouldn't be at home as he was working in the city til late. We made love again. I was beginning to become his submissive bottom and he was my dominant top.

Over the next few weeks I found I wanted to repeat visits to be with Francis at the same time as when Sue was next door with Steve. I became obsessed with hearing them fucking at the same time as we were. It made me feel like a virtual cuckold! Francis was no fool and cotton on to my frequent visits while they were together screwing. He eventually demanded why I never actually called in to see Steve but I always made up some excuse that I didn't have time or he was too busy to see me. I eventually told Francis the truth and he thought it was a big joke and I should be ashamed of myself for being so devious and sly.

"I think l need to teach you a lesson now the truth's come out" said Francis.

I didn't know what he was meaning but the next time l visited Francis he showed me what the lesson he had prepared for me.

He forced feminised me!

Francis stripped me naked and shaved my whole body, so l was completely smooth and applied women's creams and perfume body spray. I was given pink panties and bra, stockings, and 4 inch heels, and a pretty little red dress, a long blond wig and make up. To finish the transformation Francis named me his Vivien.

From then on I became his sissy bitch and cross dressed for Francis every time we met. And my sissy life became a reality! Vivien, was my fem sissy name and shemale role and for the next six months l became Francisco's sissy sub bottom.

As for my relationship with Sue everything came to a head one morning whilst lying in bed with Sue. She wanted me to do it doggy style with her as she was feeling horny. It was a surprise to me, so I obliged, and got a small 4.5" inch erection. She kept her legs together so she could squeeze any thickness from my slim dick as much as possible. I couldn't stop thinking how many times Steve had fucked her in so many positions that it sent me crazy thinking about it. Once my cock was inside Sue she moaned a little (of course faking it) and then she began to rotate her ass. All I knew was how different from the past her well used pussy felt. I could hardly feel my tiny clitty touch her inside pussy walls. Sue's cunt had been so well stretched by Steve"s humongous cock!

"Come on...Fuck me harder...Come on...You stupid bastard...Fuck me with everything you got!" Sue screamed at me.

But my little cock was no competition to the huge man sized cock she'd been enjoying with Steve these past months. I couldn't stop myself from sputtering out the words:

"Sorry...really I'm so sorry darling. I'll never satisfy you like Steve's been doing!"

Sue smartly pulled away from me, turned to lie on her back and began to curse me for being a small dick loser, saying Steve was 100 times the man I could never be. She called me a useless little pee thing. She got up off the bed, and as she got fully dressed she said:

"I knew you knew I was sleeping with Steve by the way you have lately been looking at me with those sad dooey eyes. Put up with it loser because it's the best sex I've ever had. I've loved every minute of it with Steve. So there... stick that up your sorry ass."

Sue walked out the bedroom and half an hour later left the house to go and see Steve for the rest of the day and night at his flat. I accepted what she said was true. Steve came round on his bike the next day to give his version of the situation. I asked him how long he'd been sleeping with Sue and he said more or less every week since that first bike ride. She had come round to the flat and seduced him within minutes and of course he obliged her wishes. He bragged that he soon had Sue achieving her very first orgasms with a real man.

I asked Steve if he now wanted to live with Sue but he laughed at the idea and said he'd rather just keep fucking my girlfriend until it got boring. I said I was okay with the arrangement and then I had to tell him that I'd been seeing his next door neighbour Francis after I'd spied on them. Steve laughed so loud when I disclosed that his old college pal had been screwed by his gay neighbour, whilst he was screwing his girlfriend.

Steve stood up to leave and said:

"So let's call it quits mate. You get what you want, I get what I want. I always knew you were a lying SOAB and preferred cock over pussy. You really are a sissy fucker!"

A few weeks later Sue walked out on me! She continued to see Steve for the rest of the year until he got bored with her like he said he would. The whole affair made me realise I wasn't cut out to have a straight relationship with a woman. I began to understand I'd been in denial and I was going to be much happier developing into a full and proper sissy.