Strapon
Introduction:
Oh yeah……..
Time went on and my lesbian life-style period ended; I was not a penis hater and in fact liked cock a little too much to consider myself a les so I became a lipstick or, a femme as some call us. I am feminine, well with G cup tits like mine it is hard not to be, and usually I get as much satisfaction from being fucked as I do from having my velvet tipped – for the uninitiated google tipping the velvet.
I work in advertising, which along with most creative businesses is a liberally minded industry. It’s also a business sector where PC has not extended its tentacles as far as it has in many sectors. To an extent, women are still looked on in advertising as objects, bits of stuff, eye candy and client fodder. To an avowed les that is anathema, but to me it seems perfectly natural hence, another reason for my switch to lipstick status.
Thomas was an art director at an agency for which I worked freelance. Art directors do the pictures; copywriters like me do the words. They usually work together in pairs, often closely together, sometimes very closely together. We did. Sometimes that closeness brings about extra-curricular activities. They may include working until very late and now and then, particularly before a presentation, working all night. They can also include lunching and or dining with clients, who are the kings in the ad world, visiting them at their offices, often with overnight stays and attending boozy awards ceremonies and other junkets.
Obviously, to make those creative juices flow requires stimulation. Vodka, JD and wine, weed and stuff that goes up your nose provides that. And of course that sort of stuff reduces ones inhibitions, which in turn often leads to other extra-curricular activities and Thomas and I indulged in those. We fucked before the end of the second week of our partnership.
It was not a particularly romantic setting or fuck come to that. We were the last in the agency one evening, well at least on the creative’s floor. It was after ten and we were smoking some weed. We had produced some good stuff, well we thought it was, but from experience we knew that it would need to be reviewed in the cold light of the post weed morning to tell for certain.
“Well I guess that wraps it for tonight, doesn’t it?” I asked being quite eager to get home as I had left my cat out.
“Workwise yes Tina, but does it have to?”
“How do you mean?” I asked as he got up and walked behind where I was sitting across a table from him. He put his hands on my shoulders and squeezed gently. “Does the night have to be wrapped up just yet?” He asked.
“Depends on what you have in mind,” I said my arousal sending tingles through my body.
“Well for a starter Teen, I have wanted to do this for ages,” he said sliding his hands down and cupping my tits.
That started our fling. Well to be more accurate the ensuing fuck started the fling, him cupping my tits led to the fuck.
Thomas was a dirty bugger. He was into so many different aspects of sex and sexual deviations, many of which I found daft. I was not really into BDSM as I found that all too contrived and I did not relish him tying me up or spanking me, although I have done and enjoyed both before. That sort of stuff does not go well with snorting or smoking, it’s dangerous as it fucks up one’s perspectives. And as we snorted, smoked, popped pills or drank too much each time we had sex, I stopped him doing anything like that.
I also tried to stop him indulging in water sports, but as I was in the bath one evening and he came in and peed on my face and all over my glasses, I failed miserably.
I told him a white lie in that I was slightly bi and of course he wanted me to arrange a threesome with another girl, which I said that I would provide he lined one up with another guy. We did both.
Obviously I got it on quite strongly with a fairly long-term, lady fuckmate and he went some way with the guy. He had clearly ‘played’ before and was happy to both be sucked by the other guy and suck him, but they went no further. The other guy said that gay wise he was a top, but would not do bottom. To my annoyance, Thomas declined being fucked by him. I had seen two guys fucking once before and I found it amazingly erotic.
Thomas had a big thing for anal. It was only our third date, well shag for we never really dated as such, when he wanted to fuck me there and it was only on our fourth where I let him. We were both into rimming and fingers up there and several time we lay on the bed, our arms round each other with our fingers up the other’s bum.
It was a few weeks later that we were in his flat in Bloomsbury when he said.
“You say that you would have liked to have seen me being fucked by Dave.”
“Yes, I would have done, I told you I find men together sexy, just as most blokes like seeing two birds together. Same thing really, two for the price of one.”
“I wish I had now.”
“What?”
“Let him fuck me. I need to branch out more, get new kicks, new pleasures.
“Fuck it Thomas you’ve got enough kicks already.”
“Yes but I have not been fucked have I?”
“Do you really want to be fucked up your bum?” I asked getting a little excited.
“Yes, I think I would enjoy it.”
“Well I do have a strapon if that would help.”
“Fucking hell Teen why didn’t you tell me before.”
“Simple you didn’t ask.”
*
As usual Thomas was late, he was a terrible timekeeper. I glanced at my watch and saw that it was nearly four thirty; he was half an hour late and I wondered whether he had forgotten. It was a Saturday afternoon and I knew that he and some of the agency guys had been on a big one last night. It was quite possible that he did not get home until daylight so he could still be asleep.
I was feeling well pissed off with him not even texting or calling me, when the buzzer went. I checked my appearance in the mirror and feeling pleased with my hair and the long, black, flowing gown I pressed the button to unlock the door.
“I thought you were not coming,” I said by way of a cold greeting.
“Yeah sorry I got involved in something.”
We had a couple of drinks and then he sat next to me on the sofa and put his arm round me. We kissed and his hand immediately went to my breasts. He likes my big tits and often would play with them for ages as he recovered from fucking me a first time.
“Let’s go upstairs,” I said greedily rubbing the bulge in his jeans.
We grabbed a bottle of vodka and went up to my bedroom on the top floor, the third, of the Victorian town house I own in Islington. The room is large around twenty feet square with a balcony that looks out over the back of the house with views of the tall buildings in the City.
“Oh fuck,” I said. “I forgot the gear, hang on let me go get it, why don’t you get undressed?”
I went downstairs to the ground floor and into the kitchen at the back of the house. I rummaged through a cupboard and got the tin with the joints in that I keep well hidden. I checked that there were sufficient spliffs in there and then made the long climb back up the stairs to the bedroom. When I got there I was out of breath, but thankfullyThomas was naked and nicely hard; he looked good lying in the middle of my bed. He has a great body and a lovely thick cock that was ramrod straight up his flat stomach to just past his naval.
“Mmmm, you didn’t waste much time did you?”
“No hurry I feel fucking horny.”
“Yes, you look it,” I said smiling and looking pointedly at his cock as I walked over to the bed. “I have a surprise for you Thomas.”
“Really, what is it?”
I didn’t move for a moment or two as I ran my eyes up and down his body. Then I took hold of the tie of the robe. It was more like a dressing gown really. Looking him straight in the eye, I undid the tie and let the robe fall open.
“This,” I said gripping the black strapon and pointing it towards him.
“Oh fucking hell Teen, that looks amazing,” he gasped sitting up on the bed.
Apart from the plastic phallus I was wearing only black fishnet holdups under the robe. The false cock rearing out from the base of my stomach was in stark contrast to my big tits that regrettably sagged a little due to my age and their size; the combination of the maleness of the black dick and the femininity of my breasts, however, created a powerful image.
“Want it?” I asked kneeling on the bed.
“Oh my god yes. Yes please Tina.”
I got the lube from the bedside cabinet where I had put it earlier and dropping the robe to the floor I climbed onto the bed. After covering the plastic cock with the lube as Thomas looked on, I said.
“Your turn Thomas, turn over and kneel.”
He did as I asked. I smeared the light lubricant between the cheeks of his arse and pushed my finger up him a little putting some inside him. As my finger went in he made an appreciative grunt.
“Nice?”
“Yes, you know I love that.”
“Turn over then as you ‘aint seen nothing yet.”
“Why turnover?”
“Because I say so,” I said sternly pretending to be a dom.
“Yes ma’am,” Thomas replied playing along by speaking in a submissive tone.
I pushed his legs apart, bent his legs at his knees and knelt between them with my knees fairly widely spread. I stroked his balls and ran my fingers up and down his awesomely hard dick. He has a lovely cock in that it is not spectacularly long, about seven inches I suppose, but it’s nice and thick and it stretches me wonderfully.
“Mmmm, that’s nice,” he sighed one of his hands joining mine on his dick the other gripping the artificial phallus.
“Yes it is nice, I like your cock,” I told him feeling wonderfully wanton and perverted as I prepared to fuck him. I ran my fingers down the length of his cock, over his balls across his perineum and into the crease between his cheeks. Rubbing right on his hole I asked. “Is this virgin territory Thomas, will this be your first time?”
“No.”
“Really? Who’s been up there?”
“A couple of different guys.”
“You crafty sod not telling me, before. I was rather hoping to be the first.”
“Well you will be the first woman to fuck me there.”
“Ah well that’s something,” I said smiling and pressing the lubricated, bulbous head of the strapon right against his hole. “Ready?”
Still holding his own cock with one hand he reached down and gripped my leg just by the elastic of the fishnet holdups as he grunted. “Yes, fuck me you dirty bitch.”
Although I had fucked a couple of women with it, the thrill I got as I slowly edged the cock into Thomas’ arse was awesome; everything was so much tighter than with a woman’s cunt. Actually seeing the puckered skin stretching and gripping the black cock was an amazing sight.
I felt his hold on my leg tighten and his fingernails dig into me as he said.
“Oh fuck, that hurts.”
I had got the wider head right in his hole so he was taking the worst of it, but I stopped pushing for a few moments letting his arse get used to the invader.
“Alright now?” I asked as I felt his grip loosen a little on my leg.
“Yes go on Teen, go for it,” he grunted rubbing his cock.
Putting my hands on each of his legs up near his groins I pulled gently on them as I eased my hips forward. Inch by inch the black cock vanished up his arse until it was in to the hilt. It was an incredible sight.
Pausing, I asked. “You alright Thomas.”
“Oh yes I am very alright I think it’s rubbing my prostate.”
“So does it feel good?” I asked taking hold of his cock that oddly seemed to have lost a little of its hardness. I rubbed it as I slowly started to move in and out of him.
“Oh my god, oh my fucking Lord,” he moaned.
“Is it hurting?”
“No it’s fucking gorgeous. Go harder.”
Replicating what had been done to me many times by different men I started fucking him. Deep, long, slow thrusts and then holding still with ‘my dick’ as far up him as it could go. Continuously, Thomas was moaning and sighing, rubbing his cock and reaching out for me. I leaned forward to give him my tits that he gratefully grabbed and squeezed. He pulled and pinched my sensitive nipples sending lovely feelings through me as we both rubbed his cock that had now regained its solid hardness.
“I won’t be long,” he grunted as we both rubbed his dick harder and faster.
“Then cum baby, cum,” I said leaning forward so that my tits were hovering over the end of his straining cock.
I could feel the added tension in his penis with my hand and fingers and I wanked him with long, slow strokes as I held the phallus rigid in his arsehole.
And with that he climaxed.
Surging his hips up so that his back and bottom left the bed he let out a series of grunts and groans as his cock exploded in our hands. He shot several spurts of cum in the air with most of it landing on my tits; I like that. One stream, though, outdid the others and splashed onto my glasses. We both giggled at that.
*
Whilst I was having my fling with Thomas I was also messing around with a lovely woman who I met at a reading class a few months previously. Well into her fifties and wonderfully well preserved, she was slim and beautiful with a face reminiscent of Catherine Deneuve and a rounded figure to die for. Married with two children she was a pillar of her society in Sevenoaks in Kent, a member of the local golf club and conservative party, a successful business woman and a highly respectable part of suburban Kent society. If only they knew her secret. She was extremely bi.
She owned a house in Deauville in Western France and asked me if I would like to go there with her for a long weekend. I did and we had an absolutely wonderful time.
As wanton and filthy as my fling with Thomas had become, so my few days with Sarah were elegant, stylish and romantic. As much as Thomas and my relationship was based totally on sex and sex of a depraved nature so with Sarah, it was based on affection and romance.
The house was secluded and the weather was brilliant. Thus, apart from when we went shopping or out to dinner once, we hardly got dressed, it was a unique, once in a lifetime experience and of course it was over far too soon.
Landing at Stansted in the pouring rain and getting the train into London soon brought me down to ground. And that became even more so when the evening I got home, Thomas phoned and said come round to his place adding. “And bring that fucking strapon with you.”
His flat was a tip. Well the flat wasn’t really it was just that he turned it into one. There were newspapers and magazines everywhere, books all over the place, the sink was full of dirty crockery most of the time as he would have a cleaner only twice a week; the rate at which he trashed a place he needed one twice a day! In his bedroom there were clothes on the chair, the bed and the floor, his bathrooms had used towels lying around, there were empty booze bottles, mainly vodka and JD, and used glasses
As I went in there I could not help myself from comparing it to Sarah’s place in France and thinking. ‘What a fucking difference!’ Not just that, though, but also wondering why I was again getting mixed up with men and not staying with the gentler and more elegant gender? I answered myself to that. ‘Because you like cock too much that’s why!’
“Did you bring it?” He asked as soon as I was in the flat and he was pulling me against him as he smothered my face in kisses.
“What.”
“The strapon.”
“As a matter of fact yes I did.”
“Good.”
“Why did you ask?”
“You’ll find out.”
“You want more?”
“I said you’ll find out,” he replied sliding his hand up my skirt at the back and groping my bottom that was as good as bare as I was wearing a thong.
He kissed me as he squeezed and rubbed the cheeks of my bum. Thomas was actually quite a good kisser when he put his mind to it and was not stoned or drunk. Generally, though, he was one or the other or both and then did not seem able to get his mouth in gear enough to kiss properly. In any case, we did not kiss that much. Kissing seemed to be too affectionate and intimate for what our relationship was all about. Neither of us was under any pretence about it. Our relationship was totally about sex and sex that was as extreme as it could be. We both wanted to push out the boundaries and in the other we felt we had found a soul mate, but knew we had found a fuckbuddy.
Pulling my skirt up round my waist and pushing my sweater up above my boobs he got hand one hand between my legs from behind whilst the other scooped my tits out of my bra. His mouth found and sucked my nipple as I cradled his head in my hands. I revelled in his fingers pushing the gusset of my panties up me and the sensations from his fingers on my clit and his mouth on my tits and nipple.
“Harder, bite harder,” I told him as the combination of the sensations rushed me towards an orgasm.
Some lovers like it, whilst some didn’t, but I couldn’t help it. Nearly always I came very quickly the first time. I need hardly any stimulation, provided it’s of the right sort for my mind and body to lose control and then I would shudder to my first cum. And that was nearly always beautifully satisfying as well, as acting as starter for the several more that usually follow. That’s another aspect of me that gets a divided opinion amongst my partners. I really am a multi-orgasm girl. I can easily have four or five in a session and it is not unknown for me to have three during one fuck.
“You really are a dirty bitch aren’t you?” He asked as I started to tremble in his arms and groan with orgasmic delight.
“Yes, Thomas, I am,” I groaned rubbing his cock inside his trousers.
“You hardly need touching and you cum, you’re like a bitch in heat aren’t you?”
“Yes and you bring that out in me,” I grunted as the full force of the orgasm exploded in my mind and body.
When I cum strongly, as I do usually, I tend to lose control a little, well quite a lot actually and this was no exception. Without thinking I suddenly gripped the hem of my sweater and pulled it up and over my head. I reached behind me, unclipped my bra and took that off.
“Now suck these,” I murmured pushing both of my tits against his face.
“I’m gonna suck ’em hard and not just your nipples, but your big tits as well.”
“Yes, give me love bites.”
“I’ll give you fucking love bites, is that what you want?” he grunted sucking the soft flesh on the upper part of my right tit into his mouth.
“Yes, yes I do, mark me Thomas. Leave your marks on me.”
“With these,” he said moving his mouth to my other breast and sucking that. “None of your pretty girl friends and that sexy, old tart Sarah will want to fuck you.
Looking down I saw the fierce red mark on my breast and knew that before we finished today my tits and thighs would be covered in them. That excited me.
I now had his cock out of his jeans and I was rubbing it. I slid down onto my knees and after kissing along its length I took it into my mouth and near deep throated him for a few minutes. He made all the right appreciative noises before pulling me up onto my feet and saying.
“Let’s get on the fucking bed I want to fuck you.”
“My pleasure sir,” I grinned leading the way and wiggling my naked arse at him as he followed me.
“And bring that strapon,” he ordered.
Whilst I wanted to be fucked, the memories of fucking him with the dildo rushed into my mind and that aroused me. The emotions and sensations I recalled were so powerful that I grabbed the strapon from my wag’s bag and gladly carried it with me to the bedroom.
We both finished undressing and laid on the bed side by side naked. We shared a joint and got nicely whooshy and mellow.
Then he spent some time on my tits sucking and chewing my nipples as he fingered me to another strong orgasm. Things were working well for I thought that I would be nicely sexually satisfied when I shagged him and that would enable me concentrate more on what I did to him.
“Gimme the strapon,” he said pulling his fingers out of me and licking them.
I gave it to him and was amazed when he asked. “How do you put the fucking thing on?”
Thinking he meant on me I said. “Well I need to put one leg through that loop.”
“Oh I see, I get it,” he replied sliding his foot through the loop and pulling the strapon up his legs.
I couldn’t work out either, what was going on or, what he meant when he then asked. “Now what?”
“What do you mean?”
“How do I fix the fucking thing?”
“What on you?”
“Yes I want to put it on.”
“Why?”
“Because I want to fuck you with it.”
“What?”
“You heard,” he replied managing to get the thing in place and press the clasps shut.
“Jesus you’re fucking sick,” I said, nevertheless feeling a surge of sensation when his words sunk in. Those sensations became even stronger when I looked at him.
“Am I?” he asked, stroking the false prick that came out from his stomach above his real one; they were about the same size. “You haven’t said no, have you?”
“No, I haven’t.”
“It fucking well excites you doesn’t it?”
I didn’t reply, but simply stared at the amazing sight of a guy with two dicks.
Grabbing my breast and squeezing it he went on. “It does doesn’t it Tina?”
“Yes,” I mumbled, looking down.
“So if I am sick what the fuck’s that make you?” He said laughing.
“I guess we are as bad as each other.”
“You said it babe, now get on your front and lift that arse in the air.”
I was a bit disappointed that he wanted my bum, for generally the pleasure derived from a fuck up there is nowhere near as pleasurable as up the ‘proper’ place. As I rolled onto my front, though, I was thinking that with the dildo he wouldn’t cum in my bottom so then he might fuck me with his ‘proper’ thing later. I knew the position he wanted me in so I raised my knees a little and rested my head on my arms so that my bottom and chest lifted off the bed and my tits dangled down and made them easy and convenient for him to squeeze from behind.
He slid between my opened legs and grabbed the cheeks of my bottom. He pulled them apart and I felt him wiping his spittle into the puckered skin round my anus. Then I felt the cold plastic of the strapon against it. That is one of the downsides and differences to the real thing, they don’t make dildos with the warmth that flesh and blood has!
Although I have had numerous visitors up there and Thomas had done a fair job of lubricating me, it is still a slightly painful challenge when a cock and particularly the bulbous head passes through the sphincter muscle and stretches it the opposite way to what is intended. But I knew from experience that any pain passes quickly once the head is in and the slightly thinner part of the cock slides in. The trick is to relax even though your bum feels as if it on fire. He got the head past my opening fairly quickly, but then stopped when it felt as if he was only a few inched up my back massage.
“What’s up?”
“You’ll see,” he replied.
And I did see, well feel really for suddenly the end of his real cock was pressing against the lips of my pussy and they for sure needed no lubrication at all!
“No, what are you doing,” I groaned as that too slid up me?
The surge of his hips pushing his real cock into me caused the false cock also to go deeper in me. I had been fucked before when he had also slid his finger up my bottom, but this was an entirely new ball game. The sensations were amazing.
“I am fucking both holes,” he told me gripping my tits even harder and giving me what I had never had before; double penetration.
