Training My Sissy Body Ch. 02

It's been a month and a half since first arriving at Benn's place. I've continued training almost daily, following the same routine using chastity while playing to prevent erections. I've been cumming one or two times a day using nothing but a vibrator on my flaccid cock as if it was a clitoris. This reinforces mentally that as a sissy I don't need to be hard, alongside repeating my mantras in my head while training or playing. My pleasure will come from penetration and vibration, as well as through giving pleasure to real men like Benn, with his 8" perfect uncut cock that's just the right thickness and nice and straight. He's continued to leave me in the training room most of the time, watching sissy hypno porn playlists and letting the fucking machine train me to offer no resistance when being fucked. The training has been going very well, and I no longer get erections when playing, nor has my cock tried to strain against the cage. Even night-time erections have settled down. Although the occasional time I've woken up hard, but my cock instantly softened when I woke up and tried to play with it. I liked this though, it meant my training was working, and I didn't need a hard cock anyway, other than Benn's in my ass.

Benn has been impressed with my progress. He's continued to come in during his work breaks for a blowjob or to fuck me now and then. It's the perfect relationship for him, with his busy career. He doesn't need to do anything or attend to me, he can just take what he needs when he wants it. I, in return, get all the toys and clothes I desire, and more importantly the free time to use them. I used to have to work and my wages didn't stretch to many clothes, let alone dildos and a fucking machine. He's been paying my rent just in case I decided to back out, but I moved in almost immediately after that first training session. I can't see myself leaving any time soon so may give up my place entirely.

Since my erections stopped, Benn suggested testing me even further. He told me to set up an online dating profile and see if I could find a real girl to fuck in guy mode. I felt kind of conflicted about all of this. On the one hand, this goes against everything we've been trying to achieve. On the other hand, I did used to like having sex with girls and had only ever had straight relationships before Benn. They always ended after a few years though as I started to crave dressing girly and playing with guys. I figured it would at least be nice to fuck a girl again though after such a long time. I went over to a swinging website and set myself up a guy profile, looking for a girl. I used a swingers site in the hope of finding that unicorn girl who approved of my lifestyle, but worst case I'd at least find someone wanting sex early in the dating game.

As a guy on these sites, there's a lot of competition. It's nowhere near as easy as being a tgirl where I can usually find someone needing a blowjob within ten minutes. Finding a girl to even chat to took a while. I spoke to a few where the conversation fizzled out fairly quickly. Eventually I stumbled upon Lisa, a blonde with long curly hair and a nice body. She wasn't exceptional in any way, but looked pretty in her pictures and was thin but not skinny, shorter than me but not short, you know, just sort of average. Her profile had a few saucy pictures so I could see her perky 34 C breasts, which sat perfectly without a bra, as well as her tiny patch of hair above an otherwise bare pussy. She was online in the chatroom, so I took a chance and said hi and asked what she was up to. I guess she was bored so she actually responded and we got chatting. It turned out she was not far, so I pushed my luck and suggested we go to a local bar for a casual drink and see how we get on.

We met a little later at the bar and despite both being a little nervous we found a table and ordered some drinks. Lisa said she was relieved to find someone who actually wanted to meet in real life. Apparently, most guys just want to see some boobs online, jerk off and then they disappear never to be seen again. I guess women don't have it better online after all, just different. As the drinks went down, the chat got easier and flirtier. We gradually got closer around the table until we were touching and eventually kissing. Kissing eventually turned to slightly drunken fondling when suddenly the bell sounded to indicate the bar would close soon. We moved outside, still fondling. I guess she was as horny as I was, although assume she hadn't been training to stay horny all day every day! I suggested going back to "my place" although this was of course Benn's place. He'd promised to stay out of the way in his office through the test.

We got back and went straight to my room. I'd borrowed one of the empty rooms in Benn's place for this, so I didn't have to clear out my sissy stuff and toys. We lay on the bed and while kissing pulled off each other's clothes. As I pulled her panties down, I kissed down her belly and on to her wet pussy. I licked her clit for a few seconds, and she was clearly getting into it and enjoying herself. She ran her fingers through my hair and held me against her pussy.

"Come back up the bed and let me turn around" she said, clearly feeling a little left out of the action.

I started kissing my way back up her body and paused for a moment to take her hard nipple in my mouth. Unfortunately, she was starting to kneel up so pulled out of my mouth as she turned so I lay on the bed with my head on a pillow just as she threw a leg over and knelt either side of my head. She lowered herself with her pussy pressing right into my face. She was so wet it dribbled onto my tongue just before making contact, so I thrust my tongue inside to get more of her juices before working back to her clit. She was kissing my thighs and gently licking me to tease me and get me hard before she started a blowjob.

My cock wasn't stirring at all, and in my head, I could hear myself repeating "A sissy doesn't need to get hard. Sissies leave that fucking to real men." over and over again. I couldn't help it; it had been repeated so many times over the past month that it was just stuck in my mind. I was thinking how hot it would be if there were a man here with us, we could use his cock and have some real fun.

Lisa was obviously noticing this and had given up on teasing for more direct action. She'd grasped the base of my cock between a thumb and two fingers and was squeezing in a motion which I guess she hoped would push blood into my cock. She'd pulled my foreskin back before doing this and was now licking and then sucking my completely limp cock head. Meanwhile I was still licking her clit for all I was worth, and I could feel her starting to moan.

I was totally happy eating her without reward, after all I was used to it with Benn. I guess she felt weird about it though as she pulled off my cock and said "you're not getting hard at all, aren't you into me?"

"Sorry, this has never happened before, of course I'm into you. I'll carry on and get you off if you like?"

"I don't think I want to cum alone, it's kind of weird. Besides, I want to be fucked afterwards it's been ages and I just need a hard cock inside me."

"If that's what you want you won't get it from this sissy" Benn said, pushing through the door that we'd accidentally left slightly open. Lisa started to sit up above me, clearly surprised. "I believe I can help though" he said, his 8" rock hard cock sticking out in front of him as he stepped up casually onto the bed as though it was the most natural thing in the world. Some guys just have a confidence about them, a way of fucking which just screams out "I'm taking this, and I deserve it." I don't have this, I'm the other kind of guy who asks permission. Women prefer the guys who take control, which may be why I make a good sissy and don't get many women. Lisa didn't have time to think and was clearly mesmerised by the large cock approaching her face. She was clearly very horny still from my tongue action and I guess between that and still being a little drunk she just went with it and opened her mouth to accept his cock.

As she did this, she had to straighten up which moved her pussy forwards as her hips turned. Underneath her, my tongue ended up right on her asshole, which I was happy to start tonguing. It was musky at first with a little taste but once covered in my saliva became slippery and wet, allowing my tongue to dart in and out. I heard her moan around his cock, as she wriggled to get more comfortable. She left her asshole right over my tongue though, so was clearly happy for me to carry on even though I was obviously no longer part of the sex for her. She continued to suck for a few minutes, occasionally rubbing her ass back and forth. I had also started to rub her clit and even put a finger in her pussy to rub her g-spot lightly.

Benn withdrew from her mouth, to a slightly disappointed "aw" sound from Lisa. He kneeled on the bed to the side of me and pulled her off of my face holding her thighs and bum. He pulled her down the bed and started kissing her deeply on the lips.

"I believe you said you wanted a hard cock inside of you." Benn said as he laid her back and pressed the head of his cock to her entrance.

"I don't even know who you are, where did you come from?" She said, although was clearly not putting up any resistance, and even put her arms around his neck.

"Oh, this is my house. I'm training this little slut Lucy to be a bit of a fuck toy, and this was a test for her training." He didn't stop thrusting as he carefully explained this. "She can't get hard any more. She doesn't need to as she serves real men who will do the fucking." His thrusting was getting harder and faster now, and she was no longer really listening, just moaning with pleasure. The talking had stopped, and I just lay there watching them fuck for several minutes. Lisa started to shake with pleasure and pulled him into her, digging her fingernails into his back. He stiffened and his thrusts became much slower and deeper, then he pressed into her and held his cock there while he pumped his cum deep into her. I was so horny at this point, but at no stage had my cock even started to stiffen. I'd given her pleasure and managed to pass his test.

Benn kissed Lisa deeply on the lips as he withdrew and rolled off of her towards me on the bed. I shifted out of his way as I watched his glistening cock, still almost fully hard as he relaxed. He looked at me and I knew what he wanted. I bent over and took his cock in my mouth, tasting his familiar cum mixed with her pussy juices. I licked and sucked until he was clean, he was hardening again already while I remained completely impotent.

"Clean her too, I'm sure she's ready for more too." He said, and I moved between her legs and started licking. She opened her legs to give me access.

"Does he always do this? Can't he get hard at all?"

"She is a slutty she, and she'll do what she's told. She can't get hard, no, but she's good at oral and her hole is well trained. We'll leave her for the night though, she doesn't need to play with us all night."

All I could do was listen as they discussed my status and I licked her clean. An occasional blob of cum would come out and cover my tongue as I cleaned her pussy. I could tell she was starting to get horny again. Benn could clearly see this and feel it as he played with her hard nipples and kissed her.

"Let's get to my bed so we can have some more fun." he said, getting up from the bed. I moved out of her way as she got up to join him. I nearly followed, but he turned and said "I think you should sleep with the large plug in tonight, Lucy, and keep your little chastity cage on. I want you horny in the morning so don't cum.

I wasn't sure what his plan was, but I complied anyway. He knew what he was doing, and I trusted myself to his process. I put my large plug in, which slipped in easily as expected, and put on my smallest cage which was almost flat. I didn't really feel the cage anymore so it just felt secure and safe. As I drifted off to sleep, I could hear them in the next room enthusiastically and energetically fucking. I was so horny as I drifted off. If you've ever slept with a butt plug or dildo inside you, you'll know what it does to your dreams. All night I had visions of getting fucked by large cocks, I could feel them in my dream, I wanted them. I forgot all about pussy that night in my wild dreams.

"Lucy, wake up!" Benn shouted as he carried Lisa through my bedroom door. As I opened my eyes, I saw him lower her pussy onto my face. I could smell the sex. They had been going most of the night, and I assumed he'd talked to her some more since she was clearly up for playing with me there again. I stuck my tongue out and licked as a huge gob of cum dropped into my mouth. I cleaned her pussy for a few minutes with her sitting on my face. She put her palms over my eyes as she rested on my head for support. She was grinding on my face, but with her hands in the way we made no eye contact. She was literally using me as a tongue toy to get off.

"We're going to finish the test this morning Lucy. Lisa here is a little sore from taking real cock all night, but she'll give you one more chance. She'll grind on your cock until you cum, whether you're hard or not. If you get hard then she'll fuck you properly. If not...well, I have something lined up that you'll probably enjoy more anyway." Benn unlocked my cage as he spoke, freeing my cock from its confines. I didn't get hard, but I was free. I still had the plug in, he didn't touch that. Lisa moved from my face to my cock, grinding and rubbing her wet pussy on my soft and flaccid cock. As she did this, she rubbed her tits on my face like a stripper, putting her nipples in my waiting mouth. As she bounced a little on my cock, trying to get it into her pussy, my plug pushed into my prostate. My cock was way too soft to enter her pussy, even after a night of hard fucking left it loose and wet. Any time I started to line up my cock would just slide off to the side.

"Sissies don't need to get hard, they prefer taking cocks anyway." The training repeated in my mind, blocking any attempt to enjoy this delicious and extremely willing pussy. I could feel the orgasm rising inside me, my prostate pulsing against the plug.

"No." I murmured as my cock let out spurt after spurt of hot cum without ever having penetrated her pussy. She scooper it up and fed it to me.

"Loser sissy. She didn't even start to get hard Benn." She said as I licked my cum from her fingers. "This slut will definitely prefer the club trip you're planning. How many cocks do you think she'll take?"

"Well, we'll be there for 4 hours or so, I bet she can take at least 15 but we'll count the condoms and see." I had no idea what they were planning, but it sounded like I would need my training and would get plenty of hard cock. I might have seen my last pussy, although it sounded like Lisa would be back even if not for me.