Strap on Surprise! Ch. 02

However I managed to show some restraint as he said, "God I wish I had a girlfriend like you now. You're every man's dream. Mine won't even talk about trying anal - she just stonewalls the topic when I bring it up. Something like you said you did, before your friend broke you in with a strap on."

"Have you ever done it? " I asked curiously.

"Yes I have with a few previous girlfriends. I tied one girl to a tree on Hampstead Heath, spat in her crack and fucked her up her nice tight arse -- and she really loved it! I like nothing better than a bit of backdoor action to ring the changes, but I've just had to accept that Jess doesn't have the same kink -- I'd never force her. I'm in it for the long haul with her, but I'm not able to go for the rest of my life without anal sex -- it's nice and it's good for you! I find the thought of no more butt fucking ever, very depressing."

"And I find the thought of having to watch you put Annabel through her workout very depressing as well -- I don't know if I can bear it again. I want her ass. I want to lube her hole up and pump it wearing one of my strap ons until that upper class, snotty cow squeals like a ho as she cums. I need your help!"

"Well" Sam said, "I can schedule your appointments so that they are back to back, then you know you will see her when she comes in -- you do the rest. But you have to pay in two ways. One: At some point you let me watch you getting in her arse. Two: You let me fuck your arse RIGHT NOW."

When I nodded in agreement, he took my hand and led me over to a vaulting horse. As he leaned me over the saddle and pulled my lower clothing off, I noticed how well worn the synthetic leather cover of it was, and saw what looked suspiciously like teeth marks in places. I fleetingly wondered if I was the first gym user to have been anally shafted over it. I then went on to feel a flicker of fear as I wondered whether Sam was going to try and dry hump me. But I needn't have worried about being treated with such a lack of consideration - Sam left me bent over with my bare arse hanging out and ran to the gents changing room before returning with a jar of moisturising cream.

"Neals Yard -- it's totally perfume and chemical free. It's not ideal but it'll have to do!"

I felt Sam's fingers smearing the cream liberally inside my crack and anus. There was a pause while he unzipped and treated his cock in the same manner. Then without even an attempt to get me aroused he was inside me! No kissing and no touching beforehand meant my little pucker was rather tight but it soon relaxed as he pumped into me hard, nipping at my neck as he did so. On and on it went and I started to bite down on the saddle hard to keep myself from yelling with pain -- Sam was another big man! I was just wondering whether I should call a halt, when he climaxed.

After a couple of seconds me turned me round and kissed me briefly for the first time before saying, "I'll take care of those appointments honey -- let me know what she says." Then he went off the gents to get changed.

Sam really hadn't shown a lot of finesse about the unplanned incident so I really felt like I'd been used as a fuck box as I drove home. I had been insisting on condoms with my online pickups - this was the first time I had ever tried bareback anal sex with a man. Even after showering I could feel my now rather tender anus squelch as I walked back to the car, and to be honest I found the sensation a nice souvenir of what had just happened. In fact the whole experience of being so unexpectedly buggered up against a vaulting horse had been so damn horny I wanted it to happen again. Every time I went to the gym.

I started to exercise just before closing time as often as I could manage it. Sam was always friendly and polite, but said nothing of what we had done -- it was as if it had never happened. I felt strangely disappointed as no mention of a repeat was made. He simply continued with his punishing workouts and I very quickly started to see the benefits. My ass was taut and perky. My thighs were firm and my tummy was flat for the first time since I had the kids.

"Very fuckable," said Sally as she rogered me with the strap on one Tuesday afternoon. "Your ass is the ass of a whore. He'll ask again so don't worry about it, but make him use a condom this time -- don't be such a stupid bitch! I'll spank you so hard you won't be able to sit down for a week, if you tell me you've had a barecock shag with a stranger again!"

"What about that snotty cow Annabel? How do I approach her?" I asked Sally as we hit the shower together.

"Dunno but I'm sure you'll think of something. This makes me so happy! It really does! It was me that started all this off and changed your life. If it hadn't been for me taking your ass, you would have still been with your prick of an ex!"

It was as I had just got changed a couple of weeks later that my chance came. Annabel came in -- she'd obviously travelled straight from work. She was in a smart jacket and skirt, and was immaculately made up. As she started to change into her designer gym wear, I wondered how to start chatting to her. Realising that we were the only two women in the changing room and this might be a one off opportunity I decided to ask how she found her personal training sessions with Sam, but something else came out. To this day I don't know where from.

"I'd like to take you from behind!"

The words cut through the quiet changing room like a whip. A split second later I thought I was hearing things when Annabel replied in her upper class voice:

"What with dear lady?"

"I want to take you up your nice tight arse Ms La-di-da Business Woman! Fuck you long and hard up your perfect, snotty little dirtbox with a strap on dildo until I hear you holler like the slut you really are, you stuck up mare!" I said. Then I headed for the door, signed out and drove home.

The next day I went to the gym again but there was no sign of Annabel, however I did see Sam for my personal training. Once again I was the last client so when he called time on our session, I told him how I had approached Annabel.

Sam made said nothing at all in reply as he simply took my arm and led me over to the vaulting horse. As before I was bent over and left alone while he fetched the cream. Within a couple of minutes my arse was being pounded like the last time. Thinking I'd better not tell Sally I'd been having anal bareback again, I gave in to it and bit down on the saddle again wondering how long it would take the fucker to finish up.

As before I drove home feeling as if I'd been used as a fuck box and realised I need to teach Sam to slow down. No wonder his girlfriend wouldn't let him have anal with him! But the main thing on my mind was Annabel. I wondered if she'd make a complaint about me and whether I'd see her again.

I didn't have long to wait to find out. The next time I signed in, the gym receptionist handed me a carrier bag saying it had been handed in by another member. I couldn't remember losing anything and said so, to be told the woman who had handed the bag in had been insistent that she had seen me leave it behind. A premonition warned me that I'd better investigate the bag's contents in private so I took it to my car.

I found a box wrapped in brown paper with a mobile phone number written on it. I tore the paper off to find a boxed strap on -- one of the nicest I've ever seen. The shaft itself was bright red and the panties it was attached to were black with red lace trimmings.

There were only one person I could think of who would have left a strap on at the gym reception for me. It must have been Annabel. There was no sign of her as I worked out and it was as I was leaving that she came in. Sam had obviously been on a break and he promptly appeared for their appointment.

I realised I was going to have to stay if I wanted to talk to her. By now I'd got very fit so another hour on the treadmill was no problem to me as I had the pleasure of watching that designer leotard ride up into Annabel's bottom cleavage once again. As I saw her leave I followed her, determined to make my move.

As I did so I passed Sam who said, "Remember I want to watch!"

"You should watch and learn!" I responded. "It's no wonder your girlfriend won't allow you anal sex. You're like a bull at a gate. You need to slow down and take your time with a woman, I feel like I'm being used as a fuckbox by you when you take my arse!" And with that I left the poor guy with a deflated ego, and headed off to the women's changing room.

She was there, waiting for me.

"I don't know who you are," she whispered. "Furthermore I don't know why you chose me to make those dirty disgusting suggestions to, but I want you to know that your ideas made me feel excited like never before, so I decided to buy you a present. Do you have it? Do you like it? I am married so my place is out of the question so how about your bed?"

Remembering my promise to Sam I replied, "I've got no one to have the kids after school at the moment so I can only suggest we do it here. We both have the same trainer and I know he locks up sometimes, so I am hoping that we could do this after closing time."

Annabel read my mind. For a moment I thought the deal was off then she said, "He wants to watch doesn't he? You were going to let Sam watch without my knowledge weren't you, you fucking little cumslut? But there's no need, I don't mind but he doesn't get to join in. I've bonked him once or twice and he's like a teenager -- all thrust and no finesse. Don't you agree?"

Deep down I wasn't surprised at this news about Sam sharing it with other clients, and secretly pitied his unsuspecting girlfriend. Telling Annabel of our rough sodomy sessions over the vaulting horse I went on to suggest that we show Sam how things are done properly.

"Damn right!" she said as she swept off.

As I left I told Sam he would be treated to the sight of his life, if he scheduled our appointments together. After my crushing remark about his sexual prowess he didn't take me back to the vaulting horse as I half expected, but simply said goodbye as I headed out the door.

Two days later I received a text from Sam saying he had an appointment for me later that day. Seeing that it was the hour before the gym closed I smiled in anticipation.

Later as he was giving me a particularly sadistic training session, I spotted Annabel doing circuit training and hoped I would be able to speak to her. When Sam saw her walking towards the changing room he hastily said that we had done enough for the night. As I hurried off I saw him go to an office and check the CCTV system.

I walked towards the changing room and went in.

She was standing naked - waiting for me with nothing on but a grin across her botox frozen face.

"What now?" she asked me.

As I kissed her I started to do the things I had been longing to do since I first set eyes on her. I took great delight in messing up her stupid, perfect streaked blonde hair before going on to touch her impossibly perfect shaved snatch. As I leaned her over a counter and spread her legs I wondered if she'd had a labiaplasty. Her pretty little lips were absolutely identical -- in fact her perfectly symmetrical twat reminded me of one of those medical diagrams you see online.

However the smell of it was real enough, so I inserted a finger into Annabel's vagina and slowly licked it clean in front of her shocked eyes, before I put on the strap on she'd bought me. Then I picked up the lube I bought with me for the occasion and guided Annabel back out into the gym and towards the vaulting horse. I could see Sam wanking off in his office, as he watched on CCTV.

As Annabel stood before me I kissed her again before roughly bringing her nipples up with my fingers. Then I turned her round and bent her over the vaulting horse. To be honest once I had lubed her up I just wanted to enter her and start pumping, but I remembered I'd said to Sam that I'd teach him how to fuck an arse with a bit of skill and finesse.

So I started to run my tongue along the back of her neck finishing up in her ear. As I did so I reached in between her legs from behind to find that her cunt was already open and wet for me. As I licked down the length of her spine and stuck my tongue into the crack of her arse, I wondered if the CCTV was recording me as I did this perverted thing.

Thinking it'd be fun to start off in her pussy I pulled her away from the vaulting horse, bent her over and entered her vagina from behind. As I started pumping I inserted a lubed finger into Annabel's anus and moved it in and out in time to my thrusts-- she began squealing like a cat on heat as she started fingering her clit.

Then just as she was on the point of cumming I leant her back over the vaulting horse and began moistening her tight little pucker up some more. Finally I turned her round and gave her the tube of cream, and stood pointing down at the strap on dildo. She didn't need to be told what to do. Squeezing some more lube out into her hand she took my strap on phallus and slowly greased it up, looking into my eyes as she did so.

As I bent Annabel back over the vaulting horse she spread her legs wide and allowed me to get her in position. Instead of entering her right away I teased her some more by gently licking and biting her buttocks until she begged me to let her cum. But still I wouldn't and went back to licking the crack of her ass, finally inserting my tongue into her anus again.

I felt something move behind me and realised it was Sam. As he knelt and began to lick my arse, I finally gave Annabel what she was begging for. As she continued to moan I eased the dildo into her and as I began to thrust long and hard, felt Sam's finger slide into my crack as he started biting my lower back.

I can't tell you how good it felt to pump into that snotty cow's tight little bud, and the realisation she really loved it made me even more excited. She understood the position she needed to hold immediately so that I had easy access to keep that rhythm going. On and on it went -- me thrusting into her while Sam moved his finger in and out of my backdoor. I soon discovered that I could easily touch myself as I kept the pumping action going, while holding the dildo with my other hand.

I felt Sam switch from using his finger to his tongue on my behind, and guessed that he must be wanking off. The thought of this made me want to cum as well and after pulling Annabel back from the vaulting horse so she could touch herself too, I began to finger my clit.

As the three of us moaned and grunted in unison, the sweat dripped off us in ever increasing rivulets. Flesh slid against flesh until the three of us climaxed and fell in a soaking heap of perspiring bodies. Then as we lay on an exercise mat and started to lick the sweat off each other, I realised that this was going to be the first of many such gym sessions. The thought of this made me very happy.

As the weeks turned into months I was proved right and as an added bonus Sally continued to take my ass regularly using my favourite dildo -- the Purple Pumper. However although I was getting and giving plenty of butthole action at the back of my mind there was one thing that I knew that I hadn't done.

I started to check men out constantly. Driving in my car I'd be looking at them, out jogging I'd be looking at them, and at the gym I'd be looking at them. As I zoomed in on their tight little arses I dreamed about taking a man up the arse with a strap on, and in the end the thought of trying this act became an obsession. I wondered how I could broach the subject with Sam, but when I did received an outraged refusal. Just as I was thinking of putting an ad up on Craig's List, the opportunity finally came.

I had to take my car in for its MOT and found that it needed some work done before it could pass, so I left it at the garage and took the bus home. A couple of stops on, a young guy got on and sat down next to me. Within a minute I started to suspect things weren't right as he seemed to be leaning on to me in an inappropriate way, although he didn't speak to or touch me.

Then as he stood up to let me pass to get off at my stop, my suspicions were confirmed by the bulge in his trousers. I couldn't believe the audacity of the man as he followed me off the bus!

"You can take me home if you want," was Mr Subtle's way of introducing himself.

By now I was so angry that I opened my mouth to make some cutting remark. But then I had an idea.

I said, "OK come with me..."