Life with Tamsin


With a name like Tamsin you would be right in thinking my partner was born with a sliver spoon in her mouth. I suppose Oliver sounds a bit upmarket too but we did originally meet at University, her having come from a rather upmarket private school in England and I from a Grammar School. In our first year together the relationship was developed in the few hours we had spare each week and Tamsin, though she could be as foul-mouthed as the rest of them, showed no urgency to get to bed. We hardly kissed!

I did fancy Tamsin. I had played around a lot during my later school years having lost my virginity to a girl at her 18th birthday party. Actually I suppose I actually lost my virginity to Tommy Graham a lout of a lad who had a hold over me. You could say he forced himself on me but if truth be known, my hormones were so over generating that he didn’t have to push hard and I even let him anally fuck me. I was so shocked I had to let him do it another couple of times to ensure I was really disgusted. Other students started to talk so I quickly stopped that relationship. It’s not good to be called a poof at college, especially when you’re sure you are not one, but just a horny boy.

Since I’m pouring my heart out here, I swung back and forth across the great divide during my entire time there, not fussed whether I got my cock into some randy wee lassie, or some brute forced his inside my bum. Both were sex and I was constantly hard so had to get satisfaction somewhere.

Tamsin, as far as I could make out, had lost her virginity to the boy next door when she was 18. She thought she was in love but after she gave out a couple of times, he dumped her. The guy was a bit like that as he had fucked me too! The joys of rural England in the 1990’s! In those days if you woke up in the morning and realised you didn’t like the person you had gone to bed with the night before you pissed off and vowed never to go near him or her again. Now you cry “rape.” As a local judge once said “Regret is not rape.”

Anyway, the relationship in year one was beginning to feel very brother/sisterly and that wasn’t the way I wanted it to go. Thankfully I was getting my wick dipped here and there to keep in practice but I really wanted to bed Tamsin before I started to think of her more as a sister as that would definitely poured cold water on the proceedings.

One slightly drunken night back in my shared flat I asked her outright if we would ever have sex and she just shrugged her shoulders and said, “Now if you like!”

We did and I loved it. We did it as if we had been doing it for the whole time I had known her and I discovered she was no amateur, just as happy to give as receive oral sex and screaming at the top of her voice when she reached both the orgasms she managed that night. We never looked back and had a great time over the following few months, eventually renting a flat together six months later.

We soon settled into that comfortable area that couples find where they each know what the other might be going to say. We also developed all the little short-cuts in conversation using sentences which made little sense to anyone except us. One such phrase developed around a mate of mine, Phil. Now Phil was good looking. He was a rugby type but not the heavy, beefcake sort. Six feet tall, short, messy blonde hair, striking blue eyes and a smile that could melt butter. To say Tamsin fancied him was an understatement and I used to tease her as she stumbled with words in his company. Of course Phil was oblivious to this and though he had girlfriends, sport was his passion and they rarely lasted. Eventually Phil did notice her but by that time he was way too late as I had my paws on her. He confided in me one night that he thought she was a stunner. He was drunk and asked me a number of intimate details about her and what we did. In a really pervy way I enjoyed telling him while watching his excitement.

I also took great delight in telling all this to Tamsin and she asked me what he wanted to know.

One night a few weeks later I had a blinding headache, ok, I had been drinking. Tamsin was feeling very horny but I just couldn’t get my pecker to work and after trying time and time again Tamsin said, “I’d be better trying Phil!”

“You wouldn’t do Phil?” I said.

Tamsin raised one eyebrow and smiled.

“You bugger, you would shag him if he came on to you wouldn’t you!”

She smiled again and then noticed my cock was hard.

“It seems the idea appeals to you too,” she said.

I went red-faced.

From then onwards if either of us didn’t feel like sex and the other did, the comment was, “I might just do a Phil!”

We had to be careful in front of anyone who knew him so we abbreviated it then to “P.”

Before settling down and marrying, I suggested Tamsin and I take a three week holiday somewhere warm and we both chose to explore Thailand. Though not quite back-packing we chose moderate hotels so our budget would last. The Gaziantep Oral Escort trip was to start in Bangkok and then to Phuket, Chaing Mai, Pattaya and Bangkok again before leaving.

The 33 degree Celsius humid heat hits you as soon as you leave the airport and I was thankful that we had chosen hotels over guest houses. Our Bangkok hotel was hidden up a side street off Silom Road, a long road which stretches down to the night market and Patong area of the city where the night-life was. It was quickly apparent that Tamsin’s good looks, slim body and blonde hair were turning heads both from other tourists and Thais alike. Even I was getting the eye from guys as we walked up to the hotel door. The welcoming cool air comforted us as we went to our surprisingly clean and well appointed room.

“You did well Ollie,” she said as she bounced on the king-sized double bed.

Our intention had been to head out for something to eat but we both fell sound asleep, the sort of sleep that only jet lag can create.

The next day we had some breakfast and started to be tourists, doing a river cruise, taking in the Grand Palace and looking at the Royal barges. The heat was a killer but we had a great day and went back to have a drink, shower and take in the night market. Of course once the market was explored Tamsin wanted to see some of the bars so we went up a couple of side streets and followed an invitation into a bar with a few lady boys miming to pop songs.

“They look so feminine, don’t they?” said Tamsin.

“You can say that again,” I answered.

My brain was out of sync with my cock and I found myself really attracted to these slim young “women.”

“I wonder what they do in bed?” she asked. “You know, do they play the part of women and get dick in their holes, or when they strip, are they guys and want to fuck?”

I had naturally assumed they would be effeminate little Thais and would want men to fuck them but she got me thinking when I saw one of the lady boys talking to a German couple at the other side of the bar I watched closely and nudged Tamsin as I saw money being handed to the guy at the bar and the lady boy going off with the couple, who were in their 40’s.

“Looks like they cater for all tastes,” she said. ” I always thought you fancied the idea of me with another man, and I thought of you with another woman but we’ve never had the guts. I wonder if that would kill two birds with one stone?”

“You mean take a lady boy back for sex?” I asked incredulously.

We’d had the odd fantasy about someone else joining us and also about swinging, contact sites, Craigslist etc, but it always fizzled out as we both thought we were still too young to start the wife-swapping stuff and we were both slightly jealous of the other, plus what would happen if we accidentally found someone we knew?

“One thing,” she said as if reading my mind, “We wouldn’t know anyone here. You know, what happens in Thailand, stays in Thailand?”

“Are you really serious?” I asked.

She shrugged and changed the subject as another two miming girly boys came on. Nothing more was said and as we were still both disorientated with the jet lag, I let it drop, even though my cock was hard.

The following afternoon when we were sitting in the hotel bar drinking a couple of chilled Singha beers she brought it up again.

“What would be better do you think, getting a Thai boy to fuck me or a lady boy to fuck me, or perhaps you would rather we had a Thai girl, though, to be honest, I would only watch you. I couldn’t have sex with a woman.”

“You are serious aren’t you?”, I said.

“I think if I was there while you were doing it, I would be turned on. In college, I once was in bed while my friend was fucking two boys and I was so horny I pretended to be asleep as the watching was more exciting than actually doing it. Let’s go downtown again tonight and see what happens. We would have no problem bringing someone in here.”

This was a new Tamsin to me. We had always talked about sex freely and fantasised about sex often but I never thought she would be up for doing something like this. I assumed the distance from home and the anonymity of being half-way around the world had brought out the devil in her.

As the evening turned to night we ended up back in the bar we had been in the night before. The stage seemed to be mainly lady boys though the waiters were scantily dressed Thai boys. They looked very slim and young though close up you could see they were not boys in the strictest sense. I wasn’t too attracted to the very effeminate lady boys, screaming in high-pitched voices at each other but after a couple of beers we both noticed a very slim, beautiful young lady boy. Though the features were delicate he didn’t have the long wigs and heavy make-up some used and he made eye contact with me and smiled. Tamsin noticed.

“I think you’ve made contact,” she said, smiling.

I went to the bar and talked to the older man who stood to one side and seemed to be in charge.

“What do I do if I want to take one of the lady boys?” I asked.

“You pay me 600Baht to take him out and pay him at least 1500Baht. Depending what he does you pay him more but I need him back tomorrow night,” said the man.

When I went back to tell Tamsin, the ladyboy had come across and in stilted English asked if he could sit. We struggled a bit but I bought him a drink and discovered, unlike many of the other lady boys in the bar this one was still a boy. He had had some hormone treatment and two small silicone implants to make small but attractive boobs but otherwise he was a guy. He said his name was Gan. I asked if he was gay or straight. He smiled and said he was both.

“We’re not going to get better are we?, I said to Tamsin. “I’m attracted to his slim figure and beautiful face, he’s not a girl and it looks like he might fuck! Do you want to go for it?”

“We’ll always wonder if we don’t. It might be crap but we can fuck each other thinking about it after he’s gone,” she said.

I asked Gan if he would like to come back with both of us to our hotel and he smiled, nodded, and said, “2,000Baht for both and I stay the night if you want?”

With 500Baht being around $15.00 it wasn’t going to break the bank and we might just have fun.

Thankfully Gan wasn’t too obtrusive so walking back to the hotel didn’t look too odd. I suppose a man and a woman with him didn’t look as sordid as it was. The hotel had a bar off to the right as we entered and the lift was around the corner from there. This meant we could have been going to the bar so reception didn’t even look up as we entered. We quickly escorted Gan on to the lift and up to the fifth floor,

Once inside he immediately asked to shower, which pleased us. I offered him a towel and he disappeared into the bathroom. I kissed Tamsin to reassure her but she was smiling.

“I’m feeling really dirty and horny,” she said. “I’ve always wondered,”what if” after the incident at college and I hope this might satisfy my dirty thoughts.”

I had bought some over the counter Viagra during the day, just because I could. Worried the scenario might not turn me on as much as I was hoping, I washed half of one down with a bottle of water from the fridge. I also made up some drinks and when Gan came out, he was wrapped in the towel covering all but his head and shoulders. I offered the drink and quickly dashed into the bathroom myself. Washed everywhere thoroughly and strangely, made sure my bottom was clean. Don’t ask me why but I did.

I came out, towel round waist and Tamsin went in, handing me my beer as she went. I sat with Gan and made small talk. It seems he usually went with men who wanted to fuck him. He did take cock and enjoyed it but he also enjoyed fucking men. He told me that many straight-looking guys who made a big thing out of not being sure about lady boys, often in the privacy of the room, turned over and asked to be fucked,

I caressed his arm as we sat side by side on the sofa and gently kissed his soft lips. I heard Tamsin finishing and she also came out much like Gan, wrapped in her large bath sheet.

We stood up and went across to the bed and I laid Gan down kissing his lips. I was hard and realised I hadn’t needed the Viagra after all but at least I wouldn’t have any issues down there. Gan then sat up and astride Tamsin, lying on top of her and kissing her shoulders and lips. This surprised me as I expected him to be totally passive. His hands started to wander up her legs and she let him. I was so keen to see him naked.

As he lay on Tamsin I pushed my hand up under his bath sheet and found his smooth, hairless bottom. I managed to untie the towel and pull it from him and soon I was looking at a blemish free, smooth arse. I kissed his cheeks as he ground his body against Tamsin’s legs his lips kissing her face and mouth and his tongue licking her. I could hear her gasping as his hand seemed to find his target under the towel. I pulled my towel off and my rigid 6.5 inches sprung out, curving upwards and splatted against my belly. God I was horny!

I managed to slide the towel out from under Tamsin leaving her totally naked under Gan and his hands took free reign of her body. He lowered himself down and kissed her hairless pubis the tongue then snaking lower to give her a more personal pleasure. I stroked my cock and watched this odd spectacle of a “woman” licking out my girlfriend. I lay alongside and let my hand explore his front where I could not see. I gripped a brick hard cock, uncut and about 5 inches long. It was quite thick and pre-cum was dripping from the end. His tongue was inside Tamsin as he found her little nib and started to lick it with it. Tamsin was gasping, her hands gripping the sheets as he went to town on her. He was kneeling on the floor, Tamsin in the bed, her feet on the floor and his little bum offered to me. I then did something I never thought I would, I pushed my tongue in his hole. It was tight, with a ring of darker skin around it, perhaps caused by the fuckings he had been subjected to over the last year or two. He gasped as I did it, looking around and smiling at me. This gave me impetus and I pushed my tongue even further into his hole. He was wriggling and pushing back gasping almost as much as Tamsin.

I was as horny as I could ever remember, my cock aching it was so hard. Tamsin’s groaning was also turning me on as he licked her cunt expertly. I jumped on the bed and knelt pushing my cock between them and both he and Tamsin licked it, Gan eventually taking it into his mouth and sucking, pulling back my foreskin to lick the exposed head. Traces of pre-cum trailed back from his lips as he pulled back slightly and then enveloped my cock again. He offered it to Tamsin who gripped it and took over.

Now it was Gan’s turn to be passive. He rolled on to his back, his slim young body looking extremely attractive and his small, blemish free skin and pert breasts looked beautiful, almost like a schoolgirl though we knew he was 19.

He looked at Tamsin and said, “Sit on me!”

She slid a condom on to his cute 5 inches and willingly straddled him, the cock easily sliding into her cunt. I took a few pictures as wank fodder on my cell phone as she held her hand behind her head and rode him wildly. I then put my hand between her legs to feel the delicious sensation of another cock sliding into my girlfriend’s cunt. As she was on top of him the slightly smaller cock was still achieving what it wanted with every inch driving into her. The squelching sounds of her juices were like music to my ears as she coated his cock with them.

“Oh God Oliver this is so amazing. You can’t understand what it feels like to have a part of someone else’s body sliding into you,” she gasped.

“It looks amazing from here too,” I said.

Tamsin was whimpering as she had little orgasms. She often did this as she built up to the main event and usually woke most of the neighbours at home in the process.

“You now,” said Gan.

“Oh you want me to fuck her?” I asked.

“No, you sit on it,” he replied.

“I don’t do that,” I answered.

“Try it a little bit,” said Tamsin. “You can always stop him. I would love you to feel a little of what I just did.”

I had cleaned myself but my thoughts had been more about being rimmed, not having 5 inches of rigid Thai flesh pushed into me.

Gan lay on his back and I sat with legs either side of him. Tamsin started to lubricate my hole and it was an odd sensation feeling something going in rather than the other way around. Her fingers didn’t actually hurt as she lubricated my hole using two if them. Next she rubbed some lube on his latex covered cock and I slowly sat down on the erect member. At first nothing happened and I actually commented that my hole would never take it when Gan thrust upwards and his cock slid straight inside me. There was an instant sharp pain and as I tried to lift off, he held my shoulders downward on to his cock and started to fuck me. The initial sharpness eased as the lubricant spread inside me easing his passage into my nearly-virgin arsehole.

Tamsin had my cell phone and was filming happily from behind.

I had sensations. They were odd sensations, unlike having an orgasm and yet the build up felt a bit like it. A warmth spread over my body and the grunting from this boy/woman beneath me only made me hornier. He rolled me over, lifted my legs in the air and, facing me, fucked like mad. His lips met mine and he started to kiss me. I had some kind of orgasm inside. I didn’t cum in the true sense but I was so high it was almost like being on drugs.

“Me now,” he said. “You fuck me!”

It was a command as he slid out of me and pulled his condom off. I looked at Tamsin and she nodded so I lubed him some more and pulled a condom on to my rigid cock. Gan lay back facing me just as I had with him a few minutes before. He raised his legs and his round puckered arsehole looked at me. I was horny as fuck so gave him little mercy as a slid into his hole. He gave a sharp gasp as I slid in and started fucking him.

Tamsin sat across his face, her back to me. offering her soaking cunt to his mouth and he happily licked her out as I fucked him. She gasped as he licked as best he could and my fucking was speeding up. I had to stop or I was going to fill him with my cum.

I pulled out as Tamsin asked to be fucked by us both, one after the other. I rolled her over and slid my cock straight into her, fucking her hard and kissing her beautiful breasts as I did so. She groaned with my every thrust. Gan sat alongside kissing when he could and fingering between her legs, stroking my cock as it slid in and out. I stopped as she started to climax and quickly slid out to let Gan immediately replace me. He fucked her with the urgency of youth, his smaller cock picking up the orgasmic build up and I could hear her groaning. I knew where it was going and I wanted him to bring her off rather than me.

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