Where do I start my story?

Well, my name is Alex, but my mum still insists on calling me Alexander.

I was 20 years of age when this event - is that the correct term for it? - happened.

I went to sixth-form college to get my three A-levels, in mathematics, English language and geography.

This allowed me to be accepted by Cambridge University to study economics.

Because my parents were unable to fund my life at the university, I needed to find employment. Luckily, at my first attempt, I was taken on by a large and very popular pub/restaurant. Because I was a student, they allowed me to work flexible hours. The pay wasn’t great, but at least when I was there I could eat whatever I wanted, within reason, of course.

During my first year, I was in student halls. On my floor, all the rooms were single occupancy, but a mix of males and females lived in the hall.

So here I was, 20 years of age, living for the first time away from home. And I was a virgin! Of course I had been with girls, but only the usual kissing and a bit of tit playing, nothing beyond that. So I had so much catching-up to do. To make matters worse, there was a girl four doors down the hall from my room, who I had chatted to a few times. I think she liked me; I hoped so because I really fancied her. She was from London, and from things she told me it sounded as though she had some experience in the romance area.

If the relationship evolved in a way I wanted it to, Linda - that was her name - would expect me to be able to satisfy her sexually, I presumed. Something I was convinced I couldn’t achieve.

The solution I decided, was to get professional help. I would go and see an escort. Hopefully, one who would help a young male virgin. I knew I would have to pay for her services. So in preparation, I began to save my money. Far less visits to the student bar, no unnecessary purchases and working every single hour that was offered.

Luckily, Linda was quite happy to sit and chat, study together and listen to our favourite music. I dreaded the day she would try to instigate a sexual encounter with me. But for now she was happy to just kiss and fondle a little.

After a few weeks, I counted my savings. I had accumulated £185 in total. Would that be enough? I decided I would begin to trawl the internet in search of the right lady escort. Of course, I had seen porn movies, with actors and actresses having sex in its many forms, but surely, in real life it would be nothing like that.

On this particular evening, we had been very busy in the pub, and it was a few minutes past midnight when I finally left work. The upside was, in my pocket was £23, my share of that night’s tips. More contributions to my escort fund, which would now stand at an amazing £208. Would it be enough? I still had no idea.

It was too late to call on Linda, so I went straight to my room, showered and went to bed. My first lecture the next day was not until 11am, so I could sleep in if I was still tired in the morning.

As it worked out, I was awake at my usual time. So I had a leisurely breakfast, then decided to look at escorts in this area. I got out my laptop and logged on. I typed in, ‘Escorts in the Cambridge area’, and the screen immediately filled with numerous sites offering their services. I selected a site called ‘Escorts For All’, and clicked on it. The first item to come on the screen was a choice box. I was asked to click to say I was over 18 years of age, which I did. Then it asked me to choose from; Female, Male, Couple or Trans. I clicked ‘Female’ and expected about 12 to 15 escorts to appear. To my astonishment, there were eight pages, with 10 profiles on each page. I could not believe the Cambridge area could house 80 escorts plying their trade. As I read further, it appeared many were, as they said, ‘on tour’, meaning they visited various locations throughout the country.

I began to narrow it down by eliminating certain escorts. Those on tour were ignored, as I thought I may want to re-visit the one I finally chose. Those under 35 years of age were also eliminated, as I thought a mature lady would be more likely to have patience with me. I guessed the pictures displayed may not have been totally accurate - taken years ago, Photoshopped, or in some cases not even them.

Eventually, I settled on a lady called Tamsin. She was 44 years of age, bisexual, and her profile said she was good at putting nervous clients at ease. Her photograph made her look perhaps a little younger than her age. She had a good figure, with 36B breasts, her profile read. She was 5’ 7” tall and her dress size was a 10. When it came to the section about fees, there was a list that looked like this:

30 minutes - £100.

60 minutes - £150.

Additional hours - £100.

Extra charges:

OWO (oral without condom) - £20.

CIM (cum in mouth) - £30.

Bareback (sex without condom) - £50.

Anal sex - £50.

The cost was a little more than I was expecting, but I knew there was already enough in my fund to cover it. I decided I would try one of the extras - the OWO, making the total fee £170 for the hour.

At the foot of the profile was a phone number that could be used on WhatsApp. After much thought about what I should say in the message, I finally decided what I wanted to convey to her and sent it.

During the lecture, my phone had to be on silent mode, but it could still be on vibrate. So, when halfway through it vibrated in my pocket, I looked at the screen. It was a message from Tamsin. It said, Can we chat about your message at 6pm today? I immediately sent back agreeing.

As I didn’t have to be at work in the pub until 7.30pm, chatting to her at 6pm was not a problem. After the lecture, I went to my room to study, but I was so nervous it was impossible to concentrate.

At 6pm my phone pinged. I had a message on WhatsApp. I recognised the number. It was Tamsin’s. I touched the button to answer it.

Hello Alex, how are you?

I am fine Tamsin, thank you.

A few questions, if I May ask?

Of course, ask me anything, I wrote back.

I never see anyone under 18 years of age. You say you are 20, can you prove it? If not, and I think you look too young I will refuse to see you. She stated.

I can bring my driver’s license with me.

Perfect. You say you have never had sex with a girl. What have you done so far with a member of the opposite sex?

I have fondled and kissed breasts and nipples, I wrote.

Have you ever seen or touched a girls pussy.

I have only seen one in porn movies.

You can totally forget about everything you have ever seen in porn. It is false and nothing like real life. We obviously have a lot of work to do so you are ready to make love to your girlfriend. Are you up for the challenge? She asked.

I want to do whatever it takes to be able to satisfy her. I answered.

Good. It may take more than a one-hour session to accomplish that. Are you prepared to do it?

Yes. Whatever it costs. I wrote back.

Good. You know my fees. Will there be extras? Tamsin asked.

I replied, May I add OWO to the session?

Of course. The fee will be £170, paid in cash on arrival. Is that acceptable?

Yes, completely acceptable.

Do you have a day and time in mind for the meeting? Tamsin asked me.

On Saturday and Sunday, I do not have to be at work until 5pm. So, late morning or early afternoon on either of those days is good for me.

OK, just a minute while I check my diary...I can do 12 noon on Saturday. She told me.

I wrote back, Perfect. So I will see you then.

Is there anything particular you would like me to wear when I greet you? Tamsin asked.

Oh, I never thought I had a choice. May I leave it up to you?

Ok, I will wear something to set the mood. Do you have a favourite colour? Tamsin enquired.

I said, Yes, I like blue.

That’s no problem. Come to Sutton Road and call me for the house number. Don’t be nervous Alex I will look after you.

Thank you, Tamsin, see you soon.

As I put my phone back down on the table, my palms were very sweaty.

What had I done?

I had just committed to spending £170 of my hard-earned money to have sex with a woman who I would be meeting for the first time. What if I was so nervous I couldn’t get hard? I’m sure I couldn’t ask for a refund? Tamsin told me not to be nervous, surely she has had guys like me before? Hopefully, as Saturday got closer, my nerves would settle down, and I would be able to do as Tamsin instructed me.

On the morning of the meeting, I showered, shaved, and as I had the razor in my hand, decided to shave my pubic hair as well. Used a good splash of underarm deodorant and aftershave, so I would smell pleasant for Tamsin.

As I ate breakfast, I looked at a map on my phone. I saw the street looked quite close to the halls where I was staying, and estimated I could walk there in about 30 minutes. So just in case it took me longer, I set off at 11.15. By 11.50 I was on Sutton Road. It was a mix of houses and blocks of flats. I sat on a park bench and waited until 12 noon. At exactly 12 o’clock I rang Tamsin, and he answered on the second ring.

“Is that you, Alex?”

“Yes,” I replied.

“Go to Sutton House. It is the block of flats opposite the mini-market. At the door, buzz me on number 10. The door will open.

“Go in and take the lift to floor number three. Go to flat number 10 and ring the bell.”

I did as requested, and with my nerves on a very sharp knife edge, rang the bell. The door opened, and I went inside. Standing behind the door was the most beautiful woman I had ever met in my whole life. She may well have been more than twice my age, but that did not matter one iota. Tamsin closed the door and led me into the lounge.

Tamsin was wearing lacy lingerie in dark blue. Skimpy bra and panties, a suspender belt holding up black sheer stockings. Her outfit finished off with dark-blue stilettos. Shoulder-length jet black straight hair. She was quite tall, only about an inch or so shorter than myself, with a very shapely figure that was neither stick-thin nor fat. I would say she had perfect proportions.

Tamsin took my coat off me and hung it over a chair as I handed her the money.

“Shall we go into the bedroom?” she said, taking my hand.

My mouth was so dry I could hardly speak, so I just nodded my agreement. I kicked my shoes off as we left the lounge; somehow it didn’t seem right to wear shoes in a bedroom. Tamsin took hold of my other hand and pulled me closer to her, then she kissed me gently on my lips.

“Nice, but a bit tame,” Tamsin said. “Just open your mouth a little, and try again.”

This time we kissed with more pressure on our lips, then I felt her tongue inside my mouth. It ran along my lips before going right inside and touching my own tongue. I did the same, and pushed my tongue inside Tamsin’s mouth. I was loving kissing like this. I had never experienced it before. After a few minutes, Tamsin pulled away. “Have you ever been naked in front of a girl before,” she asked me.

“Never,” I replied.

“One thing you need in that situation is confidence, you do not want to be nervous in front of your girlfriend,” Tamsin said. With that, she started to unbutton my shirt, then slipped it off until it fell onto the floor. My belt was next, followed by my trousers. Tamsin then removed my briefs and socks. Finally naked, I tried to put my hands over my cock, she gently took hold of them and held them to my sides.

“You have nothing I haven’t already seen hundreds of times,” she admonished.

So I just stood there, completely naked, in front of a woman I had only met a few minutes ago. But, my nerves had gone. It just felt so natural, surprisingly.

Tamsin put her hand on my hardening cock and smiled at me. “This is not bad for a virgin,” she said as she worked my uncut foreskin over its length. I could feel myself getting harder and harder.

“It’s not very long, I’m afraid,” I said.

“Having a long cock isn’t all it’s made out to be,” she said. “I would rather have a thick six-inch cock than a nine-inch thin one. Yours, Alex, is perfect for me, about 7 inches long I would guess, and nice and thick. I love my pussy to be stretched. We are going to have so much fun soon, I can promise you that!

“As you are naked, I suppose it is only fair I am the same.”

With that, Tamsin came over and turned her back to me, and told me to unhook her bra. With trembling hands, I undid it and put it on the bed. She stayed where she was, which I took as an invitation to fondle her breasts. I put my arms round her and cupped a breast in each hand. As I caressed them, I let my fingers gently squeeze her nipples. She moaned quietly as I continued to worship her gorgeous bust. Tamsin stepped away from me and turned round, so we were facing each other.

“Take my panties down, please,” she said.

She gently pressed down on my shoulders, suggesting I should kneel down in front of her. So I did as Tamsin wanted. I took hold of her panties at the sides and slowly pulled them onto the floor. She stepped out of them and kicked her panties away. There in front of my face was her pussy. It was so smooth, I just had to run my fingers over it. A perfect slit with gentle folds of lips on either side of it. Near the top, just inside, was a little red nub that, from watching porn, I knew was her clitoris. I could not resist the urge, and I kissed it, letting my tongue go right inside her slit.

“My, you are brave,” she said with a gasp. “Newbies don’t usually do that so quickly in a session - if at all.”

Tamsin then went and sat on the bed with her legs on the floor. She told me to kneel between her legs. Then, for the next few minutes, she instructed me on how to give a lady the most erotic oral. My lips, tongue and teeth all being used to excite every part of her labia, vagina and clitoris. At one point, her hands grabbed my hair, and forced my head into her pussy. As she got wetter and wetter, I knew I was doing something right. Eventually she pushed my head away with a gasp.

“An escort is not supposed to cum with a client, but you are such a natural at it, I couldn’t resist letting myself cum,” she whispered.

“Now, it’s your turn,” she said, sitting up. “Come and stand here.”

As I stood in front of Tamsin, she took my now rock-hard cock in her hands. She began by wanking it a few times, then brought it up to her mouth and licked the tip. Eventually it went slowly, inch by inch, into her mouth, until I felt the tip hit the back of her throat. She then worked her mouth over its entire length. Using her fingers to massage my balls at the same time. I could feel her varying the pressure on me, so as not to make me cum too quickly. When I knew I couldn’t last much longer, Tamsin took her mouth away and told me to lie on the bed.

Putting a condom on, she straddled me cowgirl style. I watched my cock slowly spread her labia as it entered her vagina. Tamsin pushed down until every part of me was buried deep inside her. Tamsin closed her eyes as she began to move up and down. Again she varied her actions to delay my climax until I could hold on no more and came with a shuddering orgasm.

After resting for a while to get our breaths back, Tamsin said, “Your time is nearly up, but because I really like you, you can stay a while longer for round two.”

“Round two?” I queried.

“Yes,” said Tamsin. “We have done me on top, now we need to try you on top,” she said with a wink.

Although I was no longer hard, I hadn’t gone back to my usual size when not aroused. So, Tamsin took me in her mouth again, and licked and sucked, using her hands as well as her mouth, to get me fully erect. She put another condom on and lay on her back, with her legs open. I could not resist seeing her like that, and started to lick her; she squirmed as my tongue worked on every part of her genitals. Tamsin tasted like nectar, and the more I licked, the more she got wet, and oozed juices, until she begged me to go inside her. I guided my cock to her entrance and started to push inside. I rode Tamsin slowly at first with long slow strokes, making sure every inch of me went inside her. Then Tamsin tightened her grip on me, wrapped her legs around my back, and gasped for me to fuck her fast and hard. I soon came, but Tamsin was still gripping me tight, so I carried on until I felt her relax and let go of me.

As I was getting dressed, Tamsin told me she had never met a newbie before who was such a fast learner as I was. But, she did caution me to take it more slowly; my girlfriend may not be ready for quite such a hectic sexual encounter as the one we had just experienced.

Just before I went out of the door, her parting words were, “Before you go home, pop into the mini-market across the road, and buy some condoms. I think you are going to need them.”