Karen AO
by Harry Bolo
Copyright© 2020 by Harry Bolo
Romantic Sex Story: How after a few years I finally connected to an old school flame who I stripped naked at during our school years.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Consensual Fiction Rags To Riches School Sharing First Oral Sex .
I was attending a film opening, one which I did part finance for my good friend Richard. We were good buddies from school and both have just turned 20. Richard was the curly hair musician and I was the class nerd. The four of us which included Keith and Paul were good friends in school.
When I left school at 17. Planning on nothing actually, I ended up writing a computer game that went ballistic. This did make me a millionaire many times over. I never told anyone of my success fearing the loss of my good friends and the money hungry vultures that want anyone money.
Coming into the red carpet area was Sandra, an old flame and her sister Karen. Well Karen and I went back many years and when she saw me, she came over and kissed me on the cheek. I turned the kiss to a lip kiss. Karen was in the year below me in school. She was a mousy brown hair skinny girl with size A boobs. Picture 30A, 20, 28. shapely legs from being a runner. Looking at her, we had not seen each other since we were 16, I hugged her.
“How did you get an invite to this?” I asked.
Karen replied “Booby sister got one but her boyfriend left her last night so she dragged me along. Now I have seen you here I am glad to be here.” I kissed her again and held her hand.
“Well now that you are here will you be my companion for the evening please. I did not bring anyone and I can see Sandra is already lining up 3 guys for the night. She has not changed.”
Karen laughed. “Yes she told me she was looking for some studs tonight. And Yes she has not changed. You should know.”
I smiled “Well when I went out with her for that two weeks, I never got pass first base. She would not let me touch her and I even think I only kissed her about 4 times. The only feel I got was when she hugged me. I’ve seen more of you that what I have seen of her.”
Karen went all red in the face. “God you don’t mean that night with Stewart when you undressed and felt me all over?”
With the biggest of grins I replied quietly in her ear “Yes and I still wank off sometimes to my memory of your sexy body. I am so glad you have not changed other that getting taller. I see you still have those sexy small boobs. Any chance of letting me play with you and them, after the evening has finished?”
Karen blushed saying softly “Yes.” She hugged my arm as we were introduced to the so called ‘A’ listed people of the event. I don’t really see how because when approached none would finance the film. When Sandra finally saw me and people being introduced to me, She realised I was important to the film. Sandra hugged me pushing her big boobs, (picture 34dd), and body into me. I laughed. “Hello Sandra, I pinching your sister from you tonight. I need a companion and I see you have already attracted some 5 boys so far.”
Sandra smiled “Yes I have to keep my sexy flexibility, Will you take Karen home if I am busy please?”
“With pleasure.” I replied.
Sandra smiled thinking she had got rid of her mousy sister, not realising I had the best part of the bargain. “Karen still lives at home but mum and dad are expecting her to stay over with me. So you can drop her off either at my flat or her home. See you later.” And she hurried off to be with the A crowd.
Karen looked at me, not happy. I smiled at her. Hugging I said “You are going to have the best evening ever. Do you have a boyfriend?”
Karen tilted her head looking at me “No boyfriend, but what do you mean the best evening?”
Smiling, I replied “I am invited to all of the after parties, so I can pick and choose which ones we go to, or we can go back to my unit in town for a quiet night. I’ll ask you later what you would like to do. OK?”
“Yes OK.” she quietly replied. I held her hand showing everyone Karen was mine.
We walked into the theatre and I was directed to the main box room. Karen looked at me in surprise. I was served an orange juice and Karen offered a juice or champagne. She took the juice. On sitting down in the box there was only the four of us. Richard, Eve his sister, Karen and myself. Introductions made, Karen held my hand in shock. She has never been treated like this before. If it was her sister she would have loved the situation. I mentioned “Just hold my hand darling, I will assist.” Karen held my hand hard. I smiled at her and kissed her forehead.
Seeing Karen tonight made the evening for me. I did not want to come but Richard insisted due to the fact I did the major financing, some $250,000. I was to get 50% of the film profit at Richard’s insistence. He need help, I help, he made sure I was rewarded. It was also a good tax break for me according to my tax accountant.
The film was shown and got an excellent review. It was picked up by the major cinemas. Richard stood up at the end of the movie and thanked his sponsors including me. I quickly stood up then sat down quickly. I held Karen’s hand. She looked at me “You helped to fund this?”
“Yes. No one would back Richard so I told him I would. It was only a small amount but I had faith in his abilities. His sister Eve was the purse strings for the film, she should get more credit. Eve got the government funding.” I replied. Eve smiled at Karen and I.
“Thank you Harry that was kind, yes I did control his spending. Richard was not happy but tonight has shown he has good director ability. Well I’m off home to my husband and Richard will take you two to the parties. I’m not interested in these parties. Too much hot air, no action or commitment. See you later Harry, Karen.” Eve stated and left us alone.
Karen looked at me. I looked at her “What the problem?”
“Doesn’t it take millions for fund films like this?” Karen asked.
“No, I only funded a small amount, which meant he could produce a quality film not a budget film and I did not fund anywhere near a million. I do have some funds but I am careful how I control it.” I replied. Karen held my arm.
Richard came back into the balcony and advised we are needed for the send off. We walked down to the send off area, I held Karen’s hand. What made Karen’s evening was the look from her sister when she was ushered out and Karen was standing in the Red Carpet area with the Actors and Director. Karen smiled at her sister squeezing my arm. I looked at Sandra and smiled.
Karen said “She is going to so kill me because I am this side with you. Thank you for inviting me to be with you.”
I laughed, “Sandra thought she had got rid of you to me not realising my involvement.” I hugged her and kissed her lips.
We went through the formalities of the night with myself introducing Karen as my girlfriend and companion. She was thrilled with this. We went to 2 parties where there was a lot of drinking and dancing. In one there was Sandra, we duck away from her. Sandra did not see us. Going on to the third party I mentioned to Richard I have had enough, enjoy yourself mate and I see you later. The driver took us home to the unit I have in town. Going up in the lift I kissed and hugged Karen again.
On entering the unit. A four bedroom penthouse over two floors. I took Karen’s hand and went to the pool. I took off her dress, shoes then removed her thong. I undressed and we entered the pool naked. The pool was warm and refreshing after this evening event. I held Karen and kissed her beautiful sexy small boobs going from one to the other suckling and running my hand down her back and bottom. I pulled her closer to me. I could feel I was very hard ready to enter her. Karen held my head and softly cried happily at my suckling. She opened her legs and sank her pussy over my rod.
I stopped, looking at her “Have you ever?”
“No” she whispered “but don’t stop I want you to do it.” and she pushed herself down on me breaking her hymen. She screamed and cried. I held her.
After she calmed down I stated to gently push in and out of her. The fact she was on top of me she started to ride me. It only took a minutes before she had an orgasm. She was wild and we were churning up the water. We continued. I tried to move her but she wanted this position. It took about 10 minutes for me to shoot. In that time Karen had cum about four/five times.
After I has shot my cum into her pussy, she held me and cried. I held her. When her tears had finished, she kissed me really hard. “Thank you, I’ve had a few boyfriends but sister always took them off me. At least, with you, I know she has no chance.” She kissed me hard again. Her tongue deep inside my mouth. We separated and got out of the pool. Dried ourselves and each other. Still naked I made a drink of juice. I do not drink any hard stuff. I do have it in the bar and asked Karen what she would like. What surprised me was she did not drink the hard stuff either as she ended up being the driver for her sister who drank like a fish. We enjoyed the juices together naked.
Karen looked around the penthouse. “Is this yours? I mean this penthouse.”
I replied “Yes, A lucky buy. Go have a look around.”
She opened the door to a bedroom and just stopped. “Is this where you sleep?”
“No.” I put my arm around her shoulder and went upstairs to the main bedroom. It was massive with an emperor size bed with satin sheets. “This is our room darling.” I lifted her up and carried her over the door threshold, pulling back the covers, I gently placed her on the bed. “Welcome to my spider web.” I moved on top of her and kissed her on the lips. I could feel my erection very hard again, Karen opened her legs and I entered her honey pot. Karen wrapped her legs around me and we raced to climax together. We fell asleep joined together. Around 3 pm I awoke, used the toilet then put the covers over Karen and myself. I quickly fell asleep again holding Karen.
I awoke around 6am feeling water running down my shoulder. It was Karen crying. I hugged her. After a few minutes she hugged me back. Lifting her head, leaning over she kissed me. I returned the kiss. I mentioned “Good morning darling Karen.”
Karen hugged me and cried again. I just held her.
After a few minutes she moved to be on top of me and kissed me again. She closed her legs around my morning hard on and presented her beautiful boobies for me to suckle. I suckled each one going from one to another. I must have spent 10 minutes on those beautiful sexy boobies. Karen reached down and mounted me. Moving to a seated position I could feel the juices and warmth of her pussy. We pumped away I held her hips then moved to suckle a boob. She came in a massive climax and I shot a load into her. We fell back in the bed exhausted.
Waking up an hour later we had a shower together. Dressing in towelling jackets we entered the kitchen and has some toast and fruit for breakfast. This time Karen had a good look around the penthouse. I sat near the pool overlooking the beach and sunrise. Karen then sat down next to me.
“What are you planning today?” Karen asked.
“Well I have done the first plan, that was making love to you. I have some emails to clear up then I am free for the day. Would you like to join me please?”
Karen smiled. “Yes please but I will need to get some clothes. Don’t you have a girlfriend or anything. You always seem to have girls around you at school?”
I replied “Most of those girls wanted to be part of a group nothing came out of any relationships. I have been on my own since leaving school. A few one night stands but when I get into a work mode I only concentrate on one thing and a lot of girls do not understand. Last night I was so very happy to see you. I still remember the time we had together on the commons. Especially the night we striped you. I so wanted to go out with you but you got that other boyfriend and I then had my sport action to complete. I would so love it it you would become my companion, lover etc as I have never forgotten you.”
Karen smiled. “Do you really mean that I could live with you for a while?”
“Yes, I would love that. You are kind, sensitive and caring. That’s what I have always loved about you. What did surprise me was last night. Have you never had sexual intercourse before?” I asked.
Karen looked away “Sort of. No I have never let anyone inside me like you last night. I wanted to wait until I was married, but seeing you and your kind actions and support last night, it just did rekindle my love for you. Yes after that night I did want to do it again, just with you but my sister started to go out with you and I was angry, that why I had a new boyfriend but as soon as I did not put out he dropped me. I tried to find you, then I found out you had a new girlfriend at skating. I retreated to study. I am planning to go to university but no idea what to study.”
I reached out to her and held her shoulder. The feeling of just being in any physical contact was exciting for me and my body responded. Karen noticed and moved to the floor. Opening my robe she held my penis and started to lick her lips. Opening her mouth Karen started to lick my pole especially just under the knob. Playing with my balls I started to pump into her mouth. I tried to grab her arm to sit on me, letting me go Karen said “Let me for-fill my dream please.” I let her carry on. She licked, sucked, wanked, tickled my balls and generally made me come close to cumming.
I finally said “I’m cumming.” Karen sucked my prick deep down her throat and did not release me until I shot my load. She drained the spunk out of me. On bring my prick out of her lovely mouth and lips Karen looked at me smiling.
“Yes I have dreamed of doing this to you since that night. If we did get together I would have done this to you any time. Any boy I have done this to I have pictured you.” Karen replied.
I lifted her up onto my lap. Opened her robe and suckled on her lovely A size boob. She held my head in a tight cuddle. I reached down and started to play with her clit. Karen came. She bounced around on me but I would not release her boob. Finally after a good minute or so, she calmed down. I released her boob and kissed her deeply. We kissed and held each other for a good ten minutes. It was such a wonderful feeling to hold Karen again in my arms. It’s hard to describe. I did not want to let her go, ever.
Just then my phone rang. I moved Karen and answered the phone. Richard asked “Where are you?”
I mentioned penthouse. “I’m coming over now.” he mentioned. I told Karen who went to the bedroom to dress. I put on some shorts and polo shirt. Richard arrived in fifteen minutes.
“Great news Harry, The movie has been picked up for both UK and US release for next Thursday.
We are required to be in London for the release. Then New York. Do you have a passport?” Richard asked.
“Yes but I’m not sure if my girlfriend has one. Karen,” she walked out from the bedroom dressed. “Do you have a passport?”
Karen looked at me surprised “Yes at home, why? O Hello Richard.”
“We are off to the UK and USA. When are we leaving Richard?”
“As soon as Eve can get the visas and passports organised. Can you see her today with your passports so she can apply for the visas please.” Richard asked.
“Sure, Karen has to go home for some clothes, we will call in on Eve later today.” I replied.
“Great, got to go, call you later mate, Hi Karen, Bye Karen.” Richard replied and left.
Karen looked at me “You want me to go with you, are you sure?”
I smiled “Come here girlfriend, yes I want you to come with me, I don’t want to go anywhere without you. Will you please come with me. I’m sorry I should have asked you.”
Karen hugged me tight “Yes I will, I love you.”
I put a finger under her chin and lifted her face to me. I kissed her replying “Yes I do love you.”
We departed for Karen place. Karen was a bit surprised with my XL Jaguar. She mentioned. “Dad will love you as he is a Jag fan.”
On arriving at her home Karen introduced me to her parents Judith & Brian. It was easy to see Karen followed her father and Sandra followed her mother in looks. On introduction Karen said “Dad you will love to see Harry car, go out with him to look whilst I get some clothes. He has invited me to a film opening in the UK and US.”
We walked out to the car. It was easy to see he was dreaming with the car. I offered him a drive. He said no the temptation was too great. Next time perhaps. We returned inside. Karen mother looked concerned about the amount of clothes she was taking. Her mother stated “Karen there is a limit to the weight of clothes you are allowed to take?”
I replied “I shall get Eve, our film production manager, to check what she needs to take. We are leaving within a day or so.”
Karen stated “Mum, Dad, I have known Harry since I was 13 and we went to school together. Sandra also knows Harry. So no need to worry. I can look after myself. Also tell Sandra, when you see her, that I thank her for taking me to the film opening last night. Harry and I finally caught up with each other. And no this is one person Sandra will never, ever, take away from me. Harry also knows her too well.” I held her hand smiling. This was the confident Karen I remember.
Getting her passport, paperwork, suitcase and makeup case we departed to see Eve.
Eve took our passports, some more passport photo’s and got up to pencil in the UK and US visa information where possible.
We departed for the penthouse. We called in downstairs and had some lunch. When we arrived in the penthouse with Karen’s bags she asked “Where shall I place these. I took her to the bedroom next to the main room and advised “This is now your room for clothes etc. It would be easier for you to have your items in here. I have too many items in the main bedroom wardrobe. This will allow you to have plenty of room to add. Did Eve take your measurements?”
Karen looked “Yes she did, Just like a tailor. Now you have me worried. Why?”
“When you go to these functions they will have designer clothes for you to wear.” I replied.
Eve rang “Ask Karen what is the range of her underwear colour is please?”
I replied “I’ll take her to get some more, can you phone ahead and advise the colours you need please. You will meet us there Ok 30 minutes.” and hung up.
“Well darling. Put on a skirt, short, and loose top please, we are going underwear shopping!” I asked.
“What, sorry I don’t have much money to pay for any clothes at present.” Karen replied.
I said “Cost is not your concern, but having your own underwear is, to make it more comfortable for you. Come on.”
Karen dressed as requested. Did she look sexy. I was ready to jump her, but I knew Eve would be upset if we did not get the clothes soon. We arrived at Victoria Secret in Broadbeach and met Eve.
Eve stated “Well you can have a few coffee’s we should be finished within an hour or so Harry. We will call you when the account is ready.” Eve took Karen into the shop, I walked into Myers for a few jeans and warm shirts. This took me about thirty minutes. I went back to the girls shop and got a coffee. Seeing the girls at the cashier I walked in and asked for the bill. It came to over two thousand dollars. I paid on credit card. When they saw the card they ladies gave excellent service.
Karen asked “Eve would not tell me the cost, How much so I can pay you back please.”
I kissed her, “When I need to get funds from you for my actions then, well,” I kissed her again.
We sat down and had coffee with Eve. She advised “I have already got your visa organised and we will be flying out in two days or so. I’ll arrange for the car to pick you up. Karen where will you need to be picked up from please?”
I advised “My place Eve.”
Eve looked at me “How long have you known each other, I thought you only met last night?”
Karen replied “At least 7 years. We went to school together, then lost contact until last night. Harry has asked me to live with him and I have agreed.” Holding my hand.
Eve replied “Well that was quick Harry?” Smiling.
I replied “Not really, I fell in love with Karen 7 years ago and did not realise until last night. I realised all my other girlfriend were either like or opposite to Karen. I’m so glad you made me go last night to the opening, so I could catch up with Karen.”
Karen looked at me “What did you not want to go last night?”
Smiling “No not really but Eve told me to attend or else.”
Karen laughed. “Funny I did not want to attend either, It was mum and dad asking me to be with Sandra to make sure she got to the function, was the reason I attended. However I am happy I did attend now.” Smirking.
Eve stated “Well it looks like you two did need to meet again. It’s good to see you smiling again Harry. Karen just make sure when he gets into a work mode you feed him. He comes up with some brilliant ideas but need thinking time, so just support him please.”
“Sure, I’ll call you, in need, if it happens.” Karen replied. Eve handed over her card and asked Karen for her phone number, which Karen gave. Eve left us to return to the office.
Karen asked “Does Eve have a crush on you?”
I replied “Did, Not now, we did go out for a while but it did not work out. We did stay as very good friends and I did attend her wedding. Tom is like her, a figures person.”
We walked into Myers and I got Karen some jumpers and a warm coat. Returning back to the penthouse, she was surprised a person was in the room.
“Karen meet James, He looks after me and cleans up after me.” I stated
James came over and shook Karen’s hand “I am his butler, manservant. I take it, it is your clothes in the 2nd bedroom young lady?”
Karen replied a bit scared “Yes, hello, what do you do here please?”
James smiled “I am his butler, I look after some of his affairs, I make sure he is awake and not working too hard. I maintain his other house. Have you known Harry long?”
Karen replied “Yes 7 years. We were school chums.” Not being prepared to say too much.
I replied “Don’t worry Karen, James knows me very well and when we return from our trip I’ll take you out to the house. James answer all or any of Karen’s questions please.”
“Yes sir. When are you leaving and where to?” James asked.
I replied “Check with Eve, in two days, UK, US. Eve has not given the timetable yet.”
“I’ll check with Eve and arrange a bag for you. Miss Karen do you mind if I pack a bag for you once I know the timetable and locations including events please. Would you like Carol to come and assist sir?”
I said “Let him Karen he knows what is needed. She will, according to Eve need this underwear. Karen, have you ever been to film openings etc?” I handed over Karen’s purchases to James for putting away.
Karen replied “No.”
I replied to James “Yes bring Carol please, tell Eve about the change.”
James walked away into the 2nd bedroom and tidied the room up placing Karen’s items away.
Karen made some drinks and mentioned “James your drink is on the bench.” Karen took our drinks onto the balcony. James thanked Karen for the drink and returned to her room.
I stated “James will have everything sorted out for you including the new items. Please Karen trust him. He has been with me for the last few years and without him I would be lost in computer gaming. He came strongly recommended and Eve did check him out. Just to let you know Eve will check you out as well, she is very protective.”
Karen asked “Why and who is Carol?”
“Carol is one of my drivers and I think James girlfriend although he will not tell me. Can I tell you my story after we come back from out trip please. It is really good for me to relax with you.”
“Sure, Harry, what ever, I’m happy to just be with you. Will he be here tonight?” Karen asked.
“No. He will make dinner for us then leave for the house. He has probably rang Eve and has plans for what clothes we need. Tomorrow he will bring two suitcases with clothes for me and then fill the other with clothes for you. He and Carol will be coming with us on the trip. They are very discrete. Please trust them.” I asked
James came out from Karen room “I will leave now and collect your things sir, you are leaving on the 8am flight tomorrow morning, I should be back to make dinner. We need to be at the airport in Brisbane by 5.30am, we should be picked up at 4.15am sir.”
I replied “Don’t worry about dinner James, We will go out for dinner and get an early night. If you are not here when we return please wake us at 3.30am.”
“Yes sir and thank you. See you in the morning, sir, Karen.” James replied and left.
Karen asked “Is he always so formal?”
I answered “Yes, I tried to get him to call me Harry, unless we are out in public and need me, he always calls me sir. Lucky he did not call you madam or lady.” Laughing.
We went back to the restaurant downstairs and had an enjoyable dinner. Returning to the bedroom I undresses Karen and pushed her backwards onto the bed. Standing over her I slowly undressed in a male strip tease fashion. I then held her ankles and tried to open her legs. She initially resisted smiling in memory. Finally opening them I keeled down and kissed along the inside of her legs to her pussy. Finally getting to the shaved area I licked her clit gently. Karen tried to push her hips up for me to speed up. I just went slowly moving my tongue downwards into her honey spot. As soon as my tongue entered, Karen grabbed my head and forced my nose into her clit and came in an almighty orgasm. I held my position with my tongue licking up her juices.
Finally she released me and collapsed on the bed arms out to the side. I used my tongue up along her body licking her belly button then each nipple finally kissing her lips. Karen reached in and put my hard cock into her warm, juicy, inviting pussy. Rolling me over she rode me until I came inside her, to which, she had another orgasm. We fell asleep half on the bed naked.
I woke about an hour later, moved Karen onto the bed correctly and covered us both. I held her and fell asleep knowing we had an early morning start.
It was 3.30am and James woke me up. He retired from the room and I awoke Karen. We had a quick shower and dressed. In her room James had laid out the outfit she was to wear. Karen was surprised of the looseness of the clothes. When we entered the kitchen, he had a mixture of tea and coffee available for us not knowing Karen choice of drink. I chose a tea, Karen had the same.
James asked “Karen I selected loose clothes as it is the best for flying, I hope you did enjoy the choice. Also are you a morning tea, coffee or juice person please?”
Karen replied “Tea and yes the clothes were fine. Thank you. I have only flown once before from Here to Perth.”
James smiled “You shall have a wonderful flight today, enjoy the comforts and if you have any questions please do not hesitate to ask. I will be very please to assist you Miss Karen!”
I asked “Eve finished the checks for that reply I see.”
“Yes sir, Eve was very happy with Miss Karen’s check and references. Very happy.” He replied.
I smiled at Karen’s look “I told you Eve is very protective and for James to say what he did means Eve is also very happy. As I requested please trust James he is a good friend and butler. He also wishes to be introduced as our butler.” James smiled and nodded his head at that remark.
His phone beeped. “Sir the car is downstairs. I’ll bring the luggage down in a minute.” We finished our tea and entered the lift down. Outside the building was a limo. Richard, Eve and Tom. A quick introduction was done and James loaded our luggage into the boot and sat with the driver Carol a very dark brown hair thin build like Karen and of similar height.
I asked Eve “I told Karen you would be checking on her. You must have been very happy by the response from James this morning?”
Eve smiled looked at Karen “Yes Karen we do like to look after our Harry. Your sister and parents were very helpful together with your employers from last year in your part time jobs. Please it’s not that we distrust you it safety for our Harry.”
Karen replied softly “OK. Harry did mention you would check me out. Thank you for the good report.”
Eve replied “You should thank you parents for their help and your former employers. Your sister though did not sound too happy when we mentioned you are travelling with Harry to the UK and US. Is there any friction there?”
I burst out laughing. “Yes, Sandra is a man eater and a must be on the A list. Karen you can deal with her on our return.” I was still smiling. Karen smiled.
On arriving at the airport James and Carol took our passports and luggage to the desk. They returned with our tickets and passports. We entered the custom area and then the executive area. James got Karen and I some tea, toast and Jam. Carol collected drinks for the others. We chatted about the launch whilst Karen remained very quiet. She was not aware or ever been treated as a special client before. James sat Carol next to her when a group of rowdy men came in saying “We will protect you. Have you ever travelled first class before?”
Karen replied quietly “No, never, will you help me so I don’t embarrass Harry please.”
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