I let the dust settle after the unexpected encounter at Al’s place. It had been set up by David and I walked into a trap. I chose to wait for David to contact me. In the meantime, I tried to work out the best way to make things less complicated. After the way Al had controlled and exploited me with his mates from his WhatsApp group, he would not be a priority, not that he ever was, as both meets with him had effectively been an ambush set up by David. He was so unrefined and was disrespectful. Despite enjoying the taste of his cum, he would not be someone I’d pursue, which then meant that David would be someone who would have to be approached with caution, so that I didn’t end up in a situation beyond my control.

At the same time, I still had feelings for Mark and didn’t want to undermine the connection we had. He was married so he liked discretion, he was clean and hygienic (unlike some of David’s and Al’s mates) and he was respectful. Mark was someone I wanted to make the most of the opportunity with, so he was a keeper and I was prepared to wait for meets with him, no matter how infrequent they were.

At the most recent session I had also met Colin, who was clean, caring and respectful. When I first met him I found him unremarkable, but the way he was with me compared to Al was overwhelming and David had the effect of making me feel safe even in a situation where I wasn’t in control. The three times he fucked me that night and the next morning were so sensual and enjoyable, like we were making love. I’d be happy to see him again and was pleased he’d asked for my number.

The other surprise from the meet was that the 20-something young guy called Will had dropped his number in my bag asking me to contact him. I had sent him a message saying he could contact me if he wanted to meet.

I’d got myself tested after being shagged bareback by three different guys. I wasn’t worried about Colin, but Al and Keith were the two that I felt that if anyone was going to pass on a disease, it was them. Whilst waiting for the results, I carried on as normal, trying not to worry and I finally got a message from Colin, I was so excited. He’d sent me different WhatsApp messages with photos from that night and the video that Al had made of Colin fucking me for the first time. I watched that over and over and decided if we did meet again, I wanted to film us fucking bareback and his cum leaking out of me. I thanked him for the messages and said I really enjoyed his company and to let me know if he’d like to meet again. His response was positive and said he’d come back to me to suggest some dates. I was very happy with that.

Whilst still waiting for my test results, I got a reply from young Will. He asked to meet me for another BJ and possibly more. I messaged back saying I’d be happy to meet again, but if we were going beyond oral, then condoms would be expected. He agreed and asked me to come to his apartment about 15 minutes away (near Al’s place) the following Saturday. I accepted and told him that if there was anyone else there expecting some action, I would leave, it had to be just him and I.

The Saturday evening arrived and because he was in an apartment block, I told him I would arrive dressed male and change at his, which didn’t seem to bother him. I arrived at his apartment which was on the 8th floor of an 11 storey block and he opened the door looking a little nervous. I asked where I could change and he showed me to his bedroom and asked me to join him in his sitting room when I was ready. I set about getting dressed, having already showered, douched and waxed before I left home. I slipped on some 20 denier black hold up stockings, black leather knee high platform stilleto boots, followed by my dark blue satin thong and matching bra. I finished off the outfit with a black leather tight micro skirt and black mesh tight top. Slipping on my wig and applying some lipstick and perfume, I finished dressing and picked up my shoulder bag that contained my lipstick, lube, condoms and butt plug. One last look in the mirror and I went to find the sitting room. As I walked in I saw it was open plan kitchen/diner/sitting room, so very spacious and the floor to ceiling windows gave a spectacular view over the surroundings. I saw Will on the sofa and he stood to greet me, still a little nervous.

‘You look great in that outfit’, he mumbled, blushing a little

‘I chose it especially for you, hoping that’s the sort of thing you like’, I said to encouraging him to relax

‘I love boots and short leather skirts, but that skirt is the best as I can see your stocking tops’, he responded, obviously gaining a little confidence

‘Well come here and show me how much you like it’, I said seductively

He didn’t hang around and threw his arms around my back, straight to my ass. Will groped and slapped it through my leather skirt and leant into kiss me. He smelt great with some unfamiliar aftershave, so I succumbed to his newly found confidence. I gently opened my lips in the hope he would slip his tongue in and he didn’t disappoint. He fought my tongue softly and his hands were moving all over my ass and back. I quickly remembered that I was there to pleasure him, rather than he pleasure me, so dropped my hand to the crotch of his pants were his young cock was growing. I had enjoyed sucking him at Al’s as his long thin cock and his bulging balls were the smoothest of all of his mates. I fumbled to unfasten the zip on his jeans so I could make contact with his flesh. Bingo! I made contact and ran my cock up his growing shaft until I reached the tip and felt his precum. I massaged that into his slit and enjoyed the moment whilst we were still in an embrace. Before long, he broke away and applied the usual pressure to my shoulders to direct me to my knees. Once in position, I unfastened his belt and unbuttoned the button on his jeans, pulling them down to find he wasn’t wearing any underwear. I leaned forward and lifted his cock to give me full access to his smooth balls, that I kissed, licked and then sucked, causing him to groan a couple of times. Taking his balls in a hand and still using the other to hold his cock up, I moved my tongue to the underside of his shaft, licking and kissing it. I moved up to his bellend and, as usual, I stuck my tongue in his slit, causing him to groan again. I licked and savoured his precum than set about wrapping my lips around his cock and getting to work, whilst still playing with his balls. He was certainly relaxed now as he started to grind his groin into my face, whilst I enjoyed the prolific amounts of tasty precum, which was really turning me on. My young stud started groaning more and more before suddenly pulling out.

‘I was close to cumming’, he breathlessly confessed, which I wasn’t surprised to hear, as I could feel his cock throbbing.

He took me towards his sofa and sat down, positioning me standing facing him, with my skirt at face level. He grabbed my ass through the leather skirt with one hand and with the other stroked my stockings down to the top of my boots and back up again, then used both hands to lift the front hem of my skirt, to properly reveal my bulging thong, which the micro skirt wasn’t doing much to hide anyway. He rubbed my cock and pushed the thong to one side before releasing it and then stroking my shaft. He gave it a quick, gentle suck before pulling away and guiding me to sit next to him.

He removed his clothes fully to reveal a relatively hair free slim body. I put my hand in his lap and turned to kiss him passionately. He spread his legs so I had full access to his cock and balls and I made the most of it. He was revving up again and getting handsy with my stockinged legs and ass, even slipping a finger into my crack and prodding at my anus. He was really charged up and pulled away to ask,

‘Is it OK to fuck you now’, with a glint in his eye

I responded by standing up to pass my shoulder bag to him to get a condom and the lube and he did what was required, handing the lube to me to make my boi pussy ready. I awaited further guidance and he stood to bend me over the arm of his sofa, lifting my skirt, pulling my thong to one side and presenting at my love hole that was eager to be filled. He slapped his sheathed cock on my ass a few times and, as I turned my head to look around, he leant forward to kiss me, then set about his business and parked his cock at my entrance. He was very careful at not rushing and edged his cock in before getting to the point of resistance. I encouraged him by pushing back, so he continued and broke through the barrier. From the noises I was making, he could tell I needed to acclimatise to his cock and waited, until I started pushing back again. With both hands on my hips, he ground away at my pussy, delving deeper and deeper, pulling back and then thrusting in again. I looked around again and he was biting his lip and had his eyes half closed. I was pleased to see he was satisfied.

‘You’re so tight, Joanna’, I’m not going to last long, he cried as he picked up his pace.

I said nothing and just let him carry on as he wished, meeting his thrusts by pushing back, before the throbbing intensified and he shouted out,

‘I’m cumming, oh yes, I’m cumming’

He kept his cock in me and leaned on my back, I turned my head to thank him and was rewarded with a kiss on the lips. I was loving this guy’s approach. He was so respectful. I felt his cock softening and slip out, so I turned round and looked him in the eyes and kissed him as I removed the full condom. I drank the contents, then for the second time that evening, I dropped to my knees and sucked his cock and started to carry out my cleaning duties. I stood once more and rearranged my skirt and thong wondering what would happen next.

Will turned his laptop on bringing up the Pornhub website and selecting some femboy porn. He left the room for me to sit down and watch a guy taking advantage of his very pretty femboy housemate. After a few moments, Will returned still naked and said,

‘We can take this to the bedroom, if you’re not in a rush to leave’, he suggested

‘No, I’m not in any hurry, after all I’m here to please you. Lead on, lover’, was my enthusiastic reply. I was glad he wanted more. I grabbed my shoulder bag and followed him. On entering the bedroom he sat at the top of the bed with his back to the headboard. He patted the space next to him and said,

‘You can keep your boots on’

I got into place and Will put his laptop between us, so that we could carry on watching the video. The femboy was being very accommodating at taking what was given to her. I knew how she felt.

I moved my hand to Will’s lap and stroked his limp cock, feeling it slowly gain some girth. I kissed him quickly and then dived to his lap, to set my mouth to work. This was one of the best cocks I’d ever had in my mouth, clean, smooth slim and tasty. I felt I was getting as much from sucking him as he was from being sucked. Will’s cock responded perfectly to the attention and filled my mouth. I was bobbing up and down and occasionally breaking away to wank him whilst looking into his eyes. He seemed to be a quick recoverer and was getting rock hard. He dragged me up to him to kiss, placed the laptop on the floor and started to lift my top off. I helped him, so that I wouldn’t dislodge my wig and spoil the moment. He then moved his hands to my thong and completely removed that, throwing it on the floor. He then leaned over, like a well trained boy, to get my shoulder bag and take a condom. Wow! This guy is a stallion if he’s ready to go again and I was ready for him. I applied lube and passed it to him, and then he lay me down, presented between my legs and held my boots in the air as he guided himself in. This time he entered quicker as my hole had already been used. He slammed away more frantically than before and then held my legs open to lean in and tongue kiss me. He was really knowing how to press all of the buttons and was even massaging my prostate with his cock. I was sensing some incredible emotions and just watched through half-closed eyes as this stud pounded my pussy, whilst I clenched his ass cheeks. Before long, the tell-tale signs were there, he was getting ready to climax and his butt cheeks tensed, then he let out a deep long breath as he filled to condom in my ass and I could feel every pulse as he jettisoned his seed into the condom. He pulled out and knew what to do. He removed the condom, but before I could drink the contents, he stuck his cock in my face and I did my cleaning routine. Then he passed me the condom and I savoured the contents like a good gurl should.

‘I want to fuck you bareback next time’, he blurted out.

‘We’ll see’, I replied without wanting to disappoint him, ‘you’ll need to get tested before we can consider that, but I’m pleased you want there to be a ‘next time’’, giving him some hope. I secretly wanted to feel his cum gushing into my pussy, but I didn’t want to admit that just yet.

It was now getting late and he layback and pulled me towards his chest to rest my head. I took my boots off and lay there with just my bra and stockings on, cuddling up to this young gentleman.

We chatted and I got to know more about him, he was 27, renting the apartment whilst saving for a deposit to buy his own place and had been girlfriend-free for 9 months. When he met me at Al’s, that was the first time he’d been with a CD and was intrigued enough to pursue it more. We both drifted off into a light sleep and after a while I awoke. It was after 1am, so I told him I should leave. He agreed, but wanted a BJ first. I knelt over him and started the action, with his gorgeous cock slowly growing. After a good deal of licking, wanking and sucking, his grunting started and he pulled out to shoot his cum on my face and into my open mouth. He pulled me to kiss him and gathered the cum for me to lick off his fingers. He was sated, so I started to gather my things.

As it was late, I didn’t bother changing back to male mode and just slipped my thong, top and boots on and made sure I’d got everything, including my shoulder bag. After a long lingering kiss, I left Will in bed and made my way out.

I chose to take the lift and, thankfully I didn’t meet anyone. Once on the ground floor I walked down the corridor and into the lobby. Crikey, there was a bloke entering the building, this may be awkward. He had a cocky strut and walked towards me eyeing me up.

‘Oh, what have you been up to you naughty gurl’, he shouted.

‘Shhh’, I said

‘I reckon you’ve been servicing a lucky neighbour, now you can give me a go’.

What a cocky git.

‘I don’t think I’m your type’, I replied abruptly

‘You have a mouth, so you’re my type, gurl’, he responded arrogantly

‘What do you want?’, I asked agitatedly

‘I wanna shove my cock in your mouth and give you a drop of the good stuff’, was the reply from the sleaze bag.

I carried on walking out to the car park and he followed me to my car. I turned round to look at him and saw he had his pants open and his cock out.

‘I’ll leave when you give this a good draining’, he shouted.

I just wanted to go home without any bother, so ‘passive me’ started making my decisions. I looked around me to see if anyone was there and beckoned him towards me. I took his average sized cock in my hand and he grabbed my face and aggressively kissed me before pushing me down. There was no time to give specific attention to his hairy balls or shaft, I just engulfed his musky cock with my mouth and went to work on him. He held the back of my head and made me gag, then released me when I choked. I carried on my duty and was relieved when he finally shot his load in my mouth, a decent load too.

‘Thanks, whore, I’ll be looking out for you round here as we could have some fun’, he said

‘Don’t count on it’, I snapped back as I got in my car throwing my bags on the passenger seat. I drove off and he was laughing and blowing kisses at me. What a creep.

I got home and went straight to bed. In the morning, I slipped on some stockings and heels, lubed up a dildo and lay on the bed slipping it in and out. My phone received a message and on seeing it was from Will, I immediately opened it.

‘I loved last night, so let me know when I can have you again. By the way, my neighbour was driving into the car park around the time you left and saw a woman giving a bloke a blow job. Did you see them?’

I just replied with an embarrassed emoji, then continued with my dildo until I exploded the contents of my balls over my stomach. The orgasm had been enhanced by the thought of my young stud wanting to see me again.

More to follow as I continue to unravel the complicated web of guys

Thank you for reading

Joanna x