The Start Of Servicing Two Women

After a rather hectic couple of days with my mature cougar Carole I felt more like resting up than getting together with my girl friend Gemma. But when I got back to my flat my flatmate Mike had said that he had been fielding calls from Gemma on my mobile which I had 'forgotten' to take with me for my weekend with Carole.

When I 'phoned' her she said that she had really missed me over the weekend but a crowd were going out for a meal and she would love me to join them. And free from exams she would love to make it up to me what I had been missing all week. As I rather reluctantly agreed to meet up with her and her university friends I thought that she would be rather shocked at just how much I hadn't missed out on sex as I had packed almost a week of sex into a couple of days with Carole.

However I simply said 'I'm a bit tired from travelling and the work over the weekend but I couldn't help thinking of your beautiful ass in that red g-string and skirt and would love you to wear it for me tonight'.

I could hear her hesitate before saying 'It's a bit gross but if you want me too I will. We are meeting at Rick's at 8.00.' This time it was me who hesitated because that's where I had been with Carole two nights previously!

I had a quick bite to eat and went to bed to sleep off my exertions of the weekend and it was nearly 7.30 before I woke and after a quick shower I didn't get to Rick's until nearly 8.30. Gemma was in the middle of a crowd of guys and girls from her year and in a white lowish cut strappy top her little tits and long nipples were well displayed and as requested I could see she had worn the skirt I liked. The top also showed off a little bit of side cleavage which I love. She looked very pretty but I couldn't help comparing her unfavourably with the body of the mature woman with whom I had just spent a no limits weekend.

I didn't have to just mentally compare them because I had hardly started my first pint when I heard a one of the guys in the company say 'That's what I call a woman' and I turned round to see Carole enter the restaurant with a good looking well preserved guy in his early fifties.

Carole looked fantastic in a black low cut and obviously very expensive dress almost slashed to the navel, very tight and clinging to her big ripe ass and about 5" above the knee teamed up with a black seamed stockings and quite high heels. She smiled as she walked past and I noticed that she sat in a position so she could look at our group. She looked exactly what she was -- a fantastically sexy woman just built for sex. There were some very complimentary comments passed about her within our group by the guys as they watched her big bum cheeks bouncing to her table and some catty ones by the women. I personally was in a state of turmoil as to whether I should acknowledge her or not as well as thinking to myself -- I've fucked that big woman they are all lusting after in virtually every way possible including buggering that big mature ass.

When I went past their table she solved it for me by getting up and offering her hand, saying 'I thought that was you -- Mark isn't it?' . Turning to her husband she said 'Bob this is the young man I was telling you about who stopped the guys bothering me in Starbucks.' As he got up to shake my hand and thank me I have to say I did feel a little bit guilty at being thanked when I had been shagging his wife all weekend.

When I came back Gemma asked how I knew them and I said I had stopped a couple of guys bothering her in Starbucks -- she rather cattily said 'Well if you're her age and showing off what you've got I suppose you've got to expect guys coming on to you.'

Anyway , cover story in place, I relaxed enough to enjoy my meal and a night with plenty to drink.

I noticed Carole having a look at Gemma as we walked past their table to the bar but I didn't see Carole and her husband leave and as Gemma normally just a wine drinker had moved on to the shorts my attention had moved to her and I enjoyed watching her pert 'though ripe ass well displayed in the red g-string and sheer skirt going and coming from the loo.

We moved on to another bar with Gemma getting increasingly drunk and quite amorous and in spite of my exertions the previous night I was soon felling randy again -- to my shames probably thinking I would enjoy the contrast of taking Gemma's slim body after having had serious fun with Carole's ripe one.

When we got a taxi back to my flat as we kissed there was very little ceremony about me getting Gemma's top off and groping her firm little 32A tits. With her long nipples they had a different appeal to Carole's big dangling 40c's but I still found them sexy in a different kind of way. In fact the complete contrast between their two bodies was a turn on -- one slim and youthful and the other mature and ripe.

Small tits bouncing I pulled her through to the bedroom and taking her skirt off I admired her long slim thighs with the exciting space between them which led to her very pretty little shaven pussy. Again I couldn't help thinking of the difference between this pretty little pussy mound and the girlish pussy lips and Carole's big handful of pussy mound and insatiable box in which I had spent quite a bit of the weekend. .

She rather melted against me whispering ' I have really missed being with you and I have looked forward to this all weekend.'

To my shame I said 'Would you like to show me how much?'

She smiled and rather drunkenly said ' I'm all yours.'

In a fit of lust I turned her round and bending her over the bed I grated 'Well what about that ass of yours?'

'We've tried that before and it hurt.'

'Well I've been wanting it all weekend since I saw your ass in the g-string and sheer skirt and I'm sure most of the guys tonight felt the same. That ass of yours is made for buggering and I want to be the one to break you in.'

Pulling her string aside I parted her hips and tongued her little brown puckered hole. I heard her murmur 'mmm that's quite nice.' So I tried to insert a finger and hear her say ' Don't just let's make love as normal.' With a few drinks in me this really did annoy me that my girl friend would refuse me what a big mature married woman had enjoyed giving me all weekend, so I persisted.

Again she resisted so I went to the bathroom and found some shaving gel which I splashed between her pert 34" hips before once again starting to put my fingers into her. Once again she said ' Mark, I don't really want this -- it will hurt.'

'Gemma, I really do want to fuck you in the ass and I've been wanting to do it all weekend. Will you not at least try it?'

Rather resignedly she murmured assent and put her ass up to be ridden. I covered my very hard cock with gel and started to ease the head in. This was a totally different ball game to getting into Carole's well used anus as Gemma was very tight and not at all relaxed. However I was rock hard with lust and determined . As I forced the head into her she screamed and tried to pull away moaning that I was far too thick and was ripping her. But this just fuelled my lust more and grabbing her by her pretty girlish buttocks as she tried to pull away from me, I pushed my cock hard into her. Initially she was moaning and tried to pull away from me but soon realised I was determined and as she stopped fighting the penetration I was soon in her up to my balls. The tightness of her sphincter on my cock was really exciting and getting what I had desired for so long also drove me into something of a fenzy of lust and I totally ignore her moans 'to take it easy' as I really gave her up her virgin ass.

It was really satisfying to deposit my cum deep within her virginal bowels and as I came off she fell forward whimpering on the bed. To my shame being drink fuelled I found that the fact that I had taken her hard and it had hurt her to be arousing and as I lay embedded in her I realised I was hardening again. Kissing her on the neck I grabbed two handfuls of small tit and started to thrust gently into her again.

'Mark, it's hurting'

'I want you again -- I have wanted your rear for so long. I'll be a little more gentle and hopefully now that you're opened up it won't be as bad if you relax -- now ease back on to me.'

As she eased back on to me it reminded me of how Carole had so willingly pushed her big ripe buttocks back to take my cock up her big ass and I started to thrust deeply into Gemma. Once again she started moaning with pain which I ignored and really buggered her hard again.

This time when I climaxed my lust was completely spent and I withdrew to let her flop forward on the bed moaning that I had really hurt her and that I had ripped her anus and really bruised her inside. Having achieved my objective of giving her it up her pretty little virgin ass I did feel guilty momentarily when I saw her ass was seeping a mixture of blood and cum. But then the thought that I should have had it before now and would be enjoying it in the future replaced that thought.

When she came out of the bathroom having tidied up her rear she had sobered up dramatically and was extremely annoyed with me. She asked me to call her a taxi as she was disgusted with me for what I had done. In spite of it being nearly 3.30 I could not persuade her to stay and in fact we had a blazing row when I said you would have thought she was the only woman who had ever taken it up the ass. She said she thought that I had loved and respected her and not just simply wanted to abuse her body.

I said I did love her and loved making love to her in any way but that in future would include her ass. She said it wouldn't!

I had mixed feelings when I put her into the taxi and told her I would call her the next day. After my exertions with the two women over the weekend I slept late and Pete had gone into the library -- no real vacation for research students -- the 'phone wakened me at c 11.30. I thought it would be Gemma but to my pleasant surprise it was Carole.

She said it appeared I had a busy weekend and I could almost imagine her smile when I said I was recovery from it now. She went on to say my girlfriend was very pretty and I'm sure I had some fun with her too. I blurted out that after our weekend together I had rather blotted my copy book by insisting on taking Gemma's ass and she hadn't particularly liked it. She laughed and said most women don't find it great the first time -- she hadn't -- but as I knew she had learned to like it and she had found most men loved it. When I said I had really enjoyed having her rear and in fact everything with her over the weekend -- it had been fantastic . She said 'likewise.'

She went on to tell me that she and Bob had quite a good session on Sunday night when they got home from the restaurant and as she was sucking his cock to get him up again to ride her pussy after he had fucked her ass, he had surprised her by saying that he had got the impression that she and I had sort of fancied each other and that I was the sort of young guy he wouldn't mind her seeing discreetly -- if she had to have someone else service her. When she asked him how he would fancy a threesome with her and me she had felt him stiffen and realised that was an option we could consider. After he fucked her he admitted that he was up for anything that would stop her being an ass slut for black footballers and if I was up for it we could both service her jointly and individually.

I hadn't ever had a full sexual threesome before -- yes I had been with mates with girls who we had all groped before one of us had taken them off to shag them. But since I had heard from Carole about her being with a lot of guys I had tried to visualise what it would be like to team a woman. But to ride a woman in front of her husband and/or join with him in double teaming her was something else. I said that while I would love to see her again and I would definitely be up for sharing her with one or two mates I wasn't sure about a threesome with her hubby.

I suggested we both sleep on it and I would call her the next day.

I had some lunch and still no call from Gemma. So at 3.00pm I called her. Her friend Helen answered the 'phone and said Gemma had gone into the Uni to see the nurse but she was really pissed off with the way I had treated her. When I said 'It was no big deal -- it was only something that everyone does.' When I rather bluntly asked her did she and her boyfriend not have anal sex -- she said they did have occasionally but that he never had sent her home ripped and bleeding as I had done with Gemma. I asked Gemma to call me.

Gemma called about 5.00 and when I asked her how she was she said rather incongruously that not only was she quite badly hurt but her skirt was completely ruined as she had bled in the taxi. She had had to go to student health to get anorectal local anaesthetic cream as she couldn't even sit down. She said that she still loved me but asked me to say that I wouldn't do it again to her.

She was quite annoyed and out the 'phone down on me when I said I had really enjoyed anal sex with her and would love to do it again.

I wasn't that concerned because I knew I had a very sexy alternative already in place in Carol and called her to see her the following day for lunch.

Over the next two weeks , I didn't hear from Gemma and Carole and I had an absolute sexual ball including a session with her hubby. One night I was at a bar in town with Carole when Gemma walked in with some friends. She was shocked to see me with a much older and sophisticated woman whereas I thought Gemma looked great and realised how much I missed her. Two days later she took the initiative and called me.

Initially she said she was surprised to see me with someone so old but supposed I was getting all I wanted and needed sexually from her but then she said how much she missed me and asked me could we not just meet as friends for a drink. That drink led to us starting to go out again as a couple although I still continued to see Carole with whom I had further fun with threesomes with her husband and some of my friends and even a MMMF foursome with two of my friends.

In addition my downward spiral into sexual obsession included getting Gemma involved in a bit of sexual exhibitionism, buggering her regularly and having a couple of threesomes with my friends.