The Winsome Widow Part 2
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Getting Some Helping Hands Inside free porn video
[This is a sequel to 'Cream Buns after the party']
It had been scary towards the end of the party as I knew, if any of the hotel staff had walked in, I would have been instantly dismissed in disgrace. That’s kind of not what you need in your first job after college.
I had been asked to be bar tender in one of the hotel function rooms. I didn’t know it was a hen party and that these were all girls who knew me and used to tease me at school. I mean the teasing was OK, I kind of liked it you see.
Anyway I must explain that, whatever happens next, I was really a private sort of guy. And not being as muscular as most of my school friends, I couldn’t do team games with the other boys. In some of the school sporting activities, I even got grouped with the girls. The games teachers were just trying to give me a fairer chance.
Actually that was what the teasing was often about. I mean, as a young guy, I did look quite effeminate so that’s how I got called a sissy. But I was really good at gymnastics; it suited my figure better. It’s a more individual sport so I didn’t get to mingle with the other guys much in like communal showers and that sort of thing.
You probably won’t believe this but I really was private about myself. OK there had been that incident at school where some guys dared me to bare my bum on camera but it was all supposed to have been kept secret.
Anyway it was only really when I wore tight shirts for sports that anyone noticed my nipples. At other times I would dress modestly and I was even reluctant to show my bare arms. Perhaps I kind of overdid the modesty a bit deliberately and maybe I was like playing ‘hard to see’ or ‘hard to get’. Anyway having girls as well as guys urging me to bare my chest or show a leg (I never wore shorts), used to give me a sort of secret thrill. That’s what I mean by not minding being teased a bit, even when it came to things like ‘Who’s your boyfriend?’
In the first story ‘Moon Probed at Hen Party’ I explained how in private I used get excited about my naked body. I think it started after some guys cornered me at school. After that I got to wanting to explore my bum you see. Sometimes I would squeeze cream into my cleft; it made me feel sexy when I walked around. But I still tried to be modest in public.
What I mean is that by then I was kind of more of age. Anyway it was only a matter of popping my pants down for a couple of seconds. That’s why I am trying to explain I didn’t really mean things to happen the way they did. I think I still wanted to be that sort of person whose private parts were for me only? Yea I think so but then I began to wonder if others were still interested in me now that I had left school.
I suppose I am trying to make excuses but when the news got out, about my bum that is, at this hen party, they just went crazy. What hope did I ever have of controlling things with a gaggle of excited girls all round me?
I used to think of them all as little angels but when reality dawns it’s, yea a bit different! I won’t recount all the details because they are in the two previous stories. Anyway during the course of the party the girls not only took over my bar tender duties but once they discovered it was my bum in the pics, they took my pants down too. There was no more ‘hard to get or see’, they had got me! OK ‘why didn’t I resist?’ you might ask; and I’m afraid the truth is I couldn’t because I kind of liked it really. I mean yea it did go a lot further. It was all because they already knew me so well.
Of course they had been drinking a lot too so while I was still sober so all their inhibitions were gone. One of them had said “Let’s see if he’s a virgin”. That’s when it all started happening. They all grabbed me and made me bend over. Of course it wasn’t my idea that, at that point, they invited Brenda to join the party.
Anyway no one warned me she was a transsexual. And it got worse too when their boyfriends turned up to collect them. They were just in time to see with my bare bum over the arm of a sofa and Brenda pulling a big slimy dick out of my exposed cunt. She dominated me completely and all the other girls did was just watch me getting it..
Brenda had this fixation that I needed to be feminised. “Look at his nipples! he’s practically one of us. [meaning transsexual] He’s certainly no real guy, he’s far too pretty. What I’d do to him, yea? I’d like to pump his fucking femmy bum. I want to do things to him.” she had said. “I mean look at him, he needs to get it, he’s got zero future as a guy!”
So after Brenda had finished doing me, I got fucked by all the guys, didn’t I? It was Jason’s fault that the shared rubber burst so all their cum got released up my bottom. And then the girls, ever inquisitive of my situation, discovered he had left half the rubber up me too. It got even worse (or better if you like) when Jason’s girlfriend Judith got angry with me and promised revenge because I fucked his tight hairy bum straight after he had fucked me.
So that’s us up to date with things and now they were taking me back to Sally’s place to give me ‘a good seeing to’. She was easily the most bossy of all the girls. She had all the makings of a dominatrix. Judith was hell bent on getting back at me and had said something about going off to her place for a dong. As for Brenda that was the last I saw of her that night.
I couldn’t find my clothes but the girls said they had taken them away as ‘they needed washing’; so all I had on as we left the party was a brief girls overcoat that barely covered my bare bottom.
“Hey Sally we’d better put something to cover the back seat as he’s a bit, well .. he’s a bit oozey you see. Anyone got a tampon we could stick up him?” Sheila asked giggling as we prepared to get into the car.
“No we’ve nothing, look just put your finger in or something. We don’t have far to go. Oh hang on, try this body spray thing, it’s about the right size.”
“Right you naughty boy, we’re going to have to put this up you aren’t we? We can’t have you making a mess in my nice new car. Sally had that knack of humiliating you, so I was made to bend over while everyone watched me getting this spray canister pushed up my bum hole.
Tony was driving and I was in the backseat between Sally and Sheila. They talked excitedly across me about girly things but every time we went over the slightest bump I felt this object teasing my gland. “I bet that feels nice! I remember being in the back seat with you up me once Tony. Now don’t try and say you don’t remember!” They both giggled but he said nothing as Shirley, who was sitting in the front beside him, gave directions to her place.
“I’m just going in to get some equipment then we’ll go over to yours Sally, there’s more room there for people to see” She came out with two plastic bags, one with rubber tubes hanging out and some sort of metal frame thing which she put in the boot. “Don’t worry pretty boy, we’re going to get to the bottom of things I think!” they all collapsed into giggles. Tony looked round at me and winked.
“There you are, welcome to ‘Maison Sally’, now lets get that stuff all set up and as for you” she said casually, “Well you don’t need this jacket now do you?” So there I was in a strange house standing helplessly in the nude. The un-tanned parts of my body emphasised my immodesty.
I was very aware too of the plug up my bum hole and knew it was clearly visible sticking out from my slimy slit. I was like someone just waiting to be attended to. That was just about correct too. Some of the girls were taking close-up pics of my bum while others got excited about the stuff they had brought in from the car.
There was one big relief for me though; we were away from the hotel and there was no longer the threat of some other member of staff catching me with my pants down.
“He’s got a lovely bum hasn’t he?” said Shirley as she and then some of the other girls started grabbing at my buttocks and smacking me with their bare hands. “They’re so beautifully big and smooth aren’t they? And I really love that cleavage, oh wow! I tell you what, there aren’t many girls who’d say no to a bum like that eh? He’s got such a lovely deep sexy slit, ooh yes I think that’s where we’re going to have to go exploring aren’t we girls?”
“Yea let’s get to the bottom of it” giggled Suzy.
“OK we’ve had that joke already” Sally had just come out of one of the rooms. “Right now, looks like we’ve got my room all set up for a sissy boy! Come on now Carly darling you’re coming into my bedroom. Now doesn’t that sound exciting eh? There you are now just lie on your back on the bed. You see we’ve got to get you fixed up so we can get a really good look at you and well, we’re going to have a good look inside you too OK?. ” I had no choice really as each of my ankles were strapped up. I was in this contraption they had fixed to the bad. “OK wind him up Sheila and let’s get a proper look at him.” As Sheila wound thus handle I felt my ankles being bulled up and back to beside my face. I realised then they had me in a gyny sling.
The girls were all giggling and crowding round to get a look at me but the guys, who had brought some crates of beer seemed more interested in discussing motor bikes and football. Both Sally and Shirley had put on rubber gloves. They immediately began investigating me. They had all stripped off down to their panties. All I could see was their arms reaching down to my bum but I could feel things happening. Suddenly the door burst open. Judith had just arrived puffing and waving a huge dildo at me. It was long black and rubbery dildo about twice the thickness of a gas station filler hose.
“Brilliant you’ve got that sissy bum just where I want it. No escape now for you now is there, you cheeky little wimp? Carl, no I’m going to call you ‘Carla’, it sounds more girly; now see this!” she said trying to stuff the black thing in mouth. “You’re going to get this right up your fucking bum my boy, Oh yes I’d going to stuff it up your rectum and squeeze you out till you’ve got nothing left!” But Sally was having none of it.
“No way Judith; you wait your turn. Sheila here knows what she’s doing. Anyway first things first eh? We’ve got to get this plug out of you haven’t we? No one can see much with that up you asshole can they eh? And then he’s got to be dilated before he gets anything big up him.” It felt really sexy when she pulled it out.
“Ooh look he really is well fucked in there isn’t he girls? Look at him poor lad he’s all gaping. You’ll have to try and keep all that cum inside you darling and stop it oozing out because first we’ve got to fish out that condom haven’t we.” She turned to me. “It’ll be floating around in all that fuck inside you pretty little boy bum, won’t it darling although it’s not is little really is it?” She pinched my right buttock so hard it made me yell out.
“Ah they’re being horrible to you!” Cindy had been watching everything carefully and had a concerned look on her face. “Here let me kiss it better” she said landing a quick kiss on my bum cheek.
Sally and Sheila had each been putting fingers in me then rubbing them over their forearms. “Cum’s the best lubricant ever isn’t it girls?” Sally winked as she said it.
“Hey look Sheila would you mind lending us Tony a minute. He deserves something better to suck than that monstrous thing!” Tony had been watching me out of the corner of his eye and came over willingly offering me his erect cock. It made me feel happy and secure as I fondled his lovely manly balls. At that moment I really wanted him up me. I wanted him to fuck me up my bottom.
Sheila spoke with that calming sort of routine speak of a nurse about to begin a procedure. “Now Carly darling, just relax while we work some of this cream into your pretty little cherry. It’s special cream to dilate you; it’s just like they use for mothers giving birth you see. Now it won’t hurt a bit, it’s just so we can open you up a bit and get a really good look. It’s just as simple as that!” Then turning to Suzy, who was in a high state of excitement; “I’ll soon be ready for the spec darling. Oh good that’s it. Hey look this is a good one isn’t it! Wow this should open him right up; he’ll need to get a really thorough rectal I think won’t he.”
It was a strange sensation; it wasn’t painful I just felt something quite
smooth coming up me then somehow it just seemed to be getting bigger and bigger.
The girls were all watching closely. “Shirley could you get a glass or
something, he’s dribbling a lot. Yea that’s great. Wow darling you did get
fucked well didn’t you. Fancy you stealing all that virile spunk off our guys!
It’ not good enough you know and there’s to be no jerking my Tony off right?”
she said waiving a finger. “I shall be needing him later. Now lets have a little
peep shall we?. Ooh look he’s all lovely and pink and slimy inside isn’t he,
what a pretty boy you are. Now we’re going to have open you up a bit more
darling. Oh this is great eh girls? I bet you haven’t seen a guy like this
before.”
“Have you found the rubber?” I asked plaintively.
“Oh yes we’ve got that, it came out with all the cum darling. Now don’t you worry yourself you’re in good hands because all we’re doing now is getting right up so we can examine you properly” There was more tittering and giggles amongst the girls. For me I had never felt so humiliated, but there was more to come. Sheila was dampening the cum on her glove and forearm with a sort of soapy solution while. Judith impatiently slapped her dong on the back of my legs.
“Now darling that thing we had in you is what we call a speculum you see” Sheila liked to sound professional. “And what you’ve just had is what we call a rectal examination but we were really just having a good look inside you. Anyway now I have get right up you and have a good feel, do you understand? You’re such a sissy so we need to investigate. Now just relax and don’t be scared, I’ve got really small hands.
You might feel a little pinch then I’ll be right up you darling. It won’t hurt a bit.” I did feel it quite a lot though. There was a sharp pain as she pushed her fist into my sphincter. It took her several goes, each time I felt her getting further in, then it was as if I was drawing her hand right then her wrist and forearm into my hungry boy bum. I simply couldn’t even think of resisting, I was utterly in her power. She seemed to be coming further and further up me. I could see her shoulder moving towards me and her elbow had almost disappeared from sight. With every movement she made I was so aware of her arm was up inside me.
She was somewhere deep inside my bottom now groping my gland and all my most intimate parts. It was all amazingly sexy. Suzy was fingering and sucking my nipples while Sally teased my little cock.
All the time Sheila was chatting to the others. “You know that friend of his Derek, yea the one who took the pics. Well he’ planning a stag party isn’t he and guess who I heard they’ve got lined up to be star of the show?” she massaged my gland more purposefully as she spoke. “Yea bum-boy here I gather!”
“You don’t know half of it then!” Judith interrupted. “Jason says Gareth and his gang have definite plans yea, I think there could be a bit of a dress code too, for some eh?” she added slapping me with the dong. “Like miniskirt perhaps? but no panties will be allowed of course!”
“He’ll look good in a mini because he got lovely smooth legs haven’t you darling” Sheila said running her other hand over my thigh. Suzy giggled as she teased my nipples.
But hearing all that had sent me way over the top, I couldn’t control myself anymore. I knew Gareth was one of Jason biker friends. The idea of them ganging me was too much and with Sheila fisting my ass cunt, I started to imagine they were all up me right then. A thrilling sort of spasm was welling up in my bum, like I had been taken over by some massive rectal orgasm. It was like something absolutely huge and gigantic! I felt like I was trying to shoot cum but I couldn’t; I was powerless to ejaculate with Sheila’s arm up me.
“Ooh steady on now darling! That got you all over excited didn’t it eh? Wow that must have been good news for you then? You see, you can’t hide anything from us now can you? All your secrets are coming out!”
“Oh please let’s have a feel!” pleaded Suzy so Sheila slowly withdrew her forearm and slimy fist from my cunt hole. She tried to control things as they all wanted to get at me together. “No not all of you at once, just let Suzy go in first. No Judith your turn will come after and now let Sally have a feel after Suzy.”
Suzy gave me a nice smile as she felt around in my bum. But Sally’s hand must have been a bit bigger and she wasn’t so gentle. This was Sally the dominatrix taking control of my sex organs.
“There’s no way I’m leaving this to Judith!” she said as she reached right up inside me. “Now lets see where is it now?” I could feel her groping all around in my bottom then I suddenly got this feeling of being squeezed somehow from somewhere deep within. I had never felt like this before. “There we are. Got it!” she said triumphantly.
Then I felt this huge pressure inside me; I seemed to be getting a sort of orgasm and while my cock was still hopelessly limp I got this feeling like something was oozing from my knob . The girls were all pointing excitedly at me. I looked down and there was a pool of spunk all around my cock and pubic hairs. Sally must have squeezed me out like a tube of toothpaste.
“Come on lets get him out of this thing” It was Judith’s turn and she was unstoppable now. She had one end of the dong up her cunt “Now you’ll see that impotent sissy boy getting it doggy style. Yea get him on the mat. Now you kneel there, and come on get a guy’s cock in your mouth because you’re about to get something much fucking bigger up your ass. Wow look how his cunt’s all swollen! It looks more like a pussy than ever now eh?” Gavin obliged me with his lovely big cock. He seemed very excited and anyway all the guys wanted to see Judith in action.
The moment I was on my knees she thrust into my ass. Judith was not about to give me an easy time. It seemed like she was more used to shoving it up girls vaginas as she thrust this huge strap-on right down to it s full length. I could feel her pussy hairs against my bum cheeks. It was thrilling but painful for me and soon I found myself crying out. I just couldn’t help it. You could hear the slurping sound as my boy cunt was pumped in and out with this massive object.
“You won’t be able to do any more fucking for a while when I’ve finished with you because I’m going to milk every last single drop out of your innermost tubes you pathetic little sissy boy!”
Cindy, the pretty little girl who always wanted to protect me was screaming at her to stop. But soon she got distracted as Tony had come to my rescue.
“Hey get off me! Who’s that you fucking prick what the hell do you you’re doing. Nobody fucks me like that! Ah!” At that point she had to pull out of me.
Tony managed to stuff his rigid cock right up her bum while she was fucking me. Then, in turn, Jason tried to stuff his up Tony’s in an attempt to prevent him fucking Judith but he was too late. Other guys joined in too and it all ended in a heap of nude bodies and cum all over the place.
Tony proudly told me afterwards that despite Jason he had managed to stuff Judith’s ass and Jason hadn’t managed to penetrate his tight hole so he just ejaculated into his slit and all over his bum cheeks. Later I asked Tony why Judith had that dong. “Yea you may well ask; you see you’re not the only bi-sexual around here. With the exception of Sheila and Sally there are not many girls from our whole class who have managed to resist her advances. Sheila tells me everything!” he explained
But all that was afterwards. There I was quite exhausted lying on my side while each of the other girls fisted me in turn. They chatted to each other sharing experiences of their explorations. Did I say I was a private sort of guy? Well each of these girls took their time up me. It is such a weird but wonderful feeling to be investigated so intimately.
These female ex-school friends now knew every single detail of my most intimate sexual parts. But I felt so passive and as they ran their hands into me and looked me in the eyes I got this feeling of being mothered in some deep and very intimate way. I have never been able to forget the experience. Was I getting addicted to the feeling of female fists up my bum.
Gradually one by one the girls paired up with their guys and they were all gone apart from Cindy and myself.
“Would you mind if I had a feel too?” she asked in a kind voice. I told her I would love it. For a long time she just kissed and fondled my cherry. “That Judith is a brute of a girl, she’ll never come near me!” she said as she lovingly licked my sphincter. Then very carefully she slipped her little hand into me. She felt me all around inside in such a gentle way, it made all the others seem really course. “Will you come to bed with me?” she asked looking expectantly at my face for an answer. I couldn’t say anything but yes. I had no idea where it would lead but she seemed so nice.
After what Judith and Sally had done to me I was left quite impotent and felt really incapable of being able to provide for Cindy. I hardly felt like a guy at all.
We lay in bed in each others arms and talked until we fell asleep. Some time in the night we both woke up and things just happened like it was the most natural thing on earth. “Will you stay with me? Will you be my boyfriend?” she asked plaintively. I had replied yes almost without thinking.
Looking back it is so strange. You see I thought I was gay or perhaps that I just had to be gay because of my effeminate body. There had been times when I had tried to get girlfriends but I could never get anywhere with the ones I met. I couldn’t get them to take me seriously.
Often things would end embarrassingly in ridicule. I suppose I was straight in mind but gay in body or something like that. The other difficult thing was that although I loved being fucked by guys, especially by gangs of them, I didn’t want to live with any one guy as a life partner. I could not escape the fact that what I really needed was a woman.
“Carl I want you to know this right?”
“What is it?” I asked
“I want you to know that I know that” she hesitated and said thoughtfully “you need guys right? Yea? and I’m not going to try and stop you. In fact I would really love you to be able to see Tony and the others sometimes. I mean well, you know what I mean don’t you. I won’t be jealous. I know you need it and I would be happy for you, OK?” Cindy had way of repeating herself to emphasise a point
I couldn’t ever have imagined meeting such an understanding girl. I asked her why she wanted me rather than all those muscular guys. She simply said “Oh I know them, I’ve gone out with a few but it’s you I want. I love you Carl and I always will do.
I suppose as I got older I was less boy-like and the two of us must have seemed like any other couple. Like that room after the hen party; Sally had organised the clear up so efficiently nobody would have known anything had happened. Oh yes, I nearly forgot; the day after one of the under-managers complimented me on the way the flowers had been rearranged on the tables. I am afraid I took all the credit for it myself!
Anyway Cindy not only let me go on seeing Tony, with Sheila’s permission of course, but introduced me to some fabulous guys who were friends of her cousin. Yea Brad and Colin plus quite a few others at the local Rugby Club. They certainly supplied me with all my needs.
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Jayla
- 20.03.2023
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- Bisexual
