[b]Authors note: This story, although partly fantasy, is based on an actual relationship I had when I was 50 years old.
My girlfriend Janice and I started out our relationship very slowly, and in the beginning we were best friends more than anything. It was pretty strange to people around us because she was 19 and I was 50. Her dad had already put me through countless interrogations, as to my motives, but I was also friends with him, so he trusted me. Janice had an older brother who we didn’t see all that much, and she had an older sister Jo.
Jo was 25, single and somewhat overweight, so she had virtually no love life, and usually ended up hanging out with us. The two sisters shared a rental townhouse, and I found myself sleeping over there more often than not. The sleepovers weren’t about sex, it was usually because we had been drinking and I didn’t want to drive impaired. Although Janice and I were carrying on like best friends, I was very attracted to her and her great body, but there was no sex of any kind between us at that time. I had split up with my ex about six months prior to this time and I hadn’t got laid since, so I was pretty horny and looking for opportunities.
During one night of our drinking and partying, it was very late and the drinks were running low, so we got talking about our sex lives. We decided that we would be totally honest with each other, so I began by saying that it had been six months since I got laid, and seven months since my last blowjob. Jo was supposed to go next, but because she was acting very embarrassed, Janice started her story. She said that she has had sex 5 times with 5 different guys, and had been told that her blowjobs were awesome. She said that the last time she had sex was 6 months ago. We both looked at Jo and told her it was her turn, so she blurts out that her story would be very short, because she was still a virgin. She said that she would love to lose her virginity, but hadn’t found the right person yet. I asked her if she was looking for love or just sex to lose her cherry, and she said “I just want to get laid and lose my virginity”. I was too drunk to be feeling horny or amorous, but any other time, stories like this would have my cock throbbing. It was around 3am, so we decided that we better hit the hay, and went to our bedrooms.
As I lay in bed thinking of Janice’s smoking body and Jo’s cherry, I thought to myself that I should be hard as a rock and jerking off, but the booze killed that idea. Before I went to sleep, I heard someone up going to the bathroom, and then I heard a faint knock on my bedroom door. It was Jo asking if I was asleep yet, so I told her to come in. She came over to the bed and sat down and asked me if I minded her talking about something very personal. When I told her to go ahead, she began telling me how depressed she has been over her inability to attract guys and was worried that she would never lose her cherry. She started to cry, and this really got to me, so I sat up in bed, put my arm around her shoulder, and pulled her in for a hug. I had forgotten that I was naked (I always slept that way at Janice’s house, hoping to get lucky), and when I hugged Jo, the blankets shifted and my cock was in plain sight. Jo’s head was facing right at it, and the next thing she says to me “see I am in your bed talking about sex, and I can’t even make you hard”. It dawned on me now that my cock was exposed so I flipped the blankets over to cover it up, and then said to Jo “I have had way too much to drink, so there is no way I could get hard for anyone, so don’t take it personally”.
Jo then asked me if I had any advice for her regarding her virginity, so I said “you need to think it over very carefully as to whether you want sex or whether you want sex and feelings. I can name any number of guys that would pop your cherry for you, but you might feel very empty and used afterwards. If you want someone who cares about you to pop your cherry, you just have to be patient”. She said that she had run out of patience, and now was getting very depressed. I tried to console her by telling her that she was pretty, and there were lots of guys out there that would like to be with her. I wasn’t lying about her being pretty, but I didn’t want to bring up her weight and make her even more depressed. She was probably thirty pounds overweight, and wasn’t someone that I would have pursued sexually, but she was a great person, with a pretty face.
Jo was still crying and said that she knew nothing about sex and would probably make a fool of herself, even if she found someone. She then said that she didn’t even have a clue how to give a blowjob. I was kind of stunned that she was being so open about sex, but I felt a slight twitch in my cock, so I wanted her to continue the conversation. Jo looked at me and asked me how many blowjobs I had received from girls, and I really had to think about it. When I figured out what to say, I told her that it was probably a thousand or two, just because of my age. Jo shocked me with her next question, but it caused my cock to start growing. She asked me if I would teach her how to give a blowjob. I was almost fully hard, and the blankets were tenting, in full view. I guess the question had me so stunned that I didn’t think about whether Jo could see the tent in the blankets or not. Jo smiled and asked me if her question had caused the tent in the bed, and I instinctively put my hands in my lap to cover up. I said to her “yes, your question did make me hard, and I would be happy to teach you whenever you are ready”. Jo said that she had never seen a guy’s cock, and certainly never saw one that was hard, and wanted to know if I would mind showing her what mine looked like.
The tent was flapping now, and I could feel precum seeping from the end of my cock, so I told her to go ahead and look whenever she was ready. She sure wasn’t acting shy about this, because she peeled back the blanket and took my cock in her hand to examine it. She also felt my balls and rolled them around in her hand. I had to tell her to be careful with them, because she obviously wasn’t aware of the sensitivity. She asked if she could start her lessons tonight, now that my cock was hard, but I had reservations about us being drunk, and her waking up and feeling used. I convinced her that it would be better if we were both sober, and less tired, so we put it off until tomorrow. She released my cock, put the blanket back over it, and said goodnight.
I knew that it was going to take some discipline to get to sleep after that, and I really didn’t feel like I had any, so I got up and followed Jo, but before I got to her bedroom, I met Janice in the hallway. I was naked and my cock was standing straight out, so needless to say, I was pretty embarrassed. I tried to hide my cock with my hands and told Janice that I was headed to the bathroom. She said that’s where she was going too, but she would wait till I finished. I didn’t have to pee, so I just went in, sat for a minute until my boner settled down, then flushed and left. As I passed Janice she said she was having a real hard time getting to sleep, and wanted to know if I felt like talking after she came out. I said sure, and went back to my room and crawled under the covers and waited. When Janice came into my room, she closed the door and sat on the edge of the bed, and thanked me for agreeing to talk a while. She didn’t look all that comfortable sitting where she was, so I told her to lie down with me. We had done this many times before, since it wasn’t about sex or anything; it was just about being great friends and being comfortable with each other.
As Janice lay down beside me, I noticed that she only had on a knee length t-shirt, and because it was snug, it accentuated her 36C breasts and nice curvy bottom. Maybe it was the booze, but this was the first time I felt in lust with her and wanted to fuck her so bad. After talking for a few minutes, Janice asked me if I was tired yet, so I said not really and I’m still good if you want to keep talking. She said that she was a little cold and asked if it was okay to share my blanket, so I lifted it up, and she got under. I think both of us at that moment forgot that I was naked, but not my cock-it immediately shot straight out and started throbbing. Janice felt like cuddling close because she was still cold, so she lay on her side and put her head on my shoulder and threw her leg over mine. My cock was really jumping now, except Jo opened my door and came in, asking if we were still awake too. As I shifted to look at Jo to talk, my erect cock rubbed against Janice’s leg, and I was surprised that she didn’t move away. I told Jo to come on in and talk with us if she couldn’t sleep either, so she got on the bed on the other side of me, and slipped under the blanket. Now my cock had a dilemma. Two girls cuddled in close to me, and the blanket tented up.
Both girls had their heads on my shoulders, with Janice's hand on my chest and Jo's on my abdomen. Janice never moved her hand, but Jo was starting to move her hand down my abdomen towards my cock. I flinched slightly as her hand wrapped around my erect cock, and Janice must have noticed the change in the blanket, because she asked Jo if she was enjoying herself giving me a hand job. Jo was really embarrassed, and pulled her hand away quickly, and denied that she had done anything. Janice asked me if I put her up to this, and I said “no way, nothing happened”. Janice then said to Jo, “you have been depressed for a long time, and can’t seem to find a guy who will appreciate you, so why don’t you let him help you by teaching you things you need to know”. She reached over for Jo’s hand and placed it on my cock, and then said to me “teach her things that will help her find someone, and get her ready so she will be able to keep a guy once she finds him”.
I looked at Jo and she nodded yes in agreement, so I started the lesson. I threw back the blanket to expose my throbbing cock, and turned on the lamp beside the bed, so she had a better view. I began explaining about cocks and testicles and what felt good. Somehow my lesson seemed rather clinical and caused my cock to start going limp, and when I explained to Jo why that happens, Janice said it would be a perfect time to explain blow jobs to Jo. Janice said she wanted to help, so she told Jo to get between my legs and she would help teach her. Now my cock was in full throb mode, and was also leaking precum.
Janice explained to Jo about precum and why it was necessary. As Janice’s lesson started, she had Jo use her tongue to lick up and down my shaft, concentrating on the sensitive underside. Janice told her to alternate between my balls and cock, but to be very careful with the balls, since a lot of guys are very sensitive there. She couldn’t really get Jo to understand about ball sucking so Janice moved her head in and told Jo to watch how it’s done. I knew I was about to blow my load, so as Janice demonstrated on my balls, I reached for Jo and pulled her mouth to my cock. She was pretty dense, and didn’t seem to get the drift of things, and in less than three seconds, my cum was spraying all over her face. She yelled that it was yucky and wiped her face on the blanket, as Janice released my balls from her mouth. Janice was pissed and told Jo the lesson was over, and she should go back to her room. Jo started crying and got up to leave, but I stopped her and told her that we would get through all these frustrations, and I would turn her into a very fine fellatrix. She didn’t know what that was, so I said after tomorrow, she would be known as Fellatio Jo. I guess she had enough for tonight, and because tomorrow was Saturday and no one had to work, she agreed to resume her lessons in the morning, and went to her room.
Janice moved back up to lay her head on my shoulder, and I told her she did a very fine job sucking on my balls. She said that she was glad I liked it, but she wasn’t hopeful about Jo learning to do it properly. We talked for a while about our friendship and how well we got along, and both of us agreed that notwithstanding the age difference, we had a very special bond. I said that I had never had a friend before who sucked my balls, so she laughed and said “I hope not”. This was so cool, and I was so comfortable with Janice, I said ”would you mind doing that again for me-I loved it before, but it was way too brief”. She said that she had done it before mainly to help Jo understand how it’s done, but she would do it again, if I really wanted her to. My cock was standing tall and as she moved between my legs, I felt so lucky to have a friend this special.
Janice took me literally and focused all of her attention on my balls, and although it felt great, I thought she would know that I really wanted the full treatment. I wasn’t sure how to handle this, so I whispered to her that she was making me feel great, and asked if she was comfortable. When she took my balls out of her mouth to answer, I reached down and held her face, and moved her mouth close to my throbbing cock. She looked up at me and said “did you also want me to suck your cock”? I didn’t answer, but continued pulling her face towards my cock, until her lips touched the head. She looked up at me and said “get ready to be blown away”. Her tongue started lapping at my cock head, as her hand cupped my balls. She alternated between playful licks of the underside of my cock head, to full deep throat, rattling my balls off of her chin. I lost control and started humping her face, and felt that special tingle in my balls that signaled a load was about to erupt. She sensed it too and squeezed my balls, as she sucked and licked at my cock head, and devoured every drop of cum that shot into her mouth. I looked down at this sweet young thing and was just frozen in time. I felt like screaming in ecstasy, but restrained myself and simply whispered that I had just received the best blow job of my life. She smiled up at me, as she finished cleaning cum off of my cock head with her tongue, so I pulled her up and kissed her passionately on the lips. I swirled my tongue in her mouth, and then realized that this was the first time Janice and I had kissed. Well, it was a lot of firsts actually, but this kiss spelled something other than appreciation for the fantastic blow job. When I released Janice from the kiss, she looked at me and said “Do you know that this is our first kiss”? We both laughed and agreed that it was pretty funny that a blow job came before a kiss.
When Janice cuddled close to me she said “I hope you realize this changes everything, and our friendship will never be the same”. I replied “I hope you mean changed for the better” and I got my answer when she kissed my chest and said “for sure”. At that moment, Janice and I became lovers as well as best friends, and before we fell asleep, we both exchanged “I love you's”.
I woke up in the morning with a raging boner, and watched it start to deflate as I remembered that Jo would be coming in soon for her lesson. It wasn’t that I didn’t like the thought of more attention being paid to my cock, but it was now confusing, after the change in my relationship with Janice. I got up to pee, and when I returned from the bathroom, Jo was already waiting beside Janice in my bed. We all felt really hungry so we decided to go down to the kitchen and make breakfast. As Janice and I stood beside one another at the counter, I whispered to her “what should we do about Jo’s lessons”? She whispered back “I’m looking forward to teaching her how to please your cock, as long as you are okay with it”.
Over the course of that Saturday and Sunday, I must have had my cock and balls sucked between ten and fifteen times, and by late Sunday evening, I began calling Jo by her rightful name-“Fellatio Jo”. The thing about Jo was that she was so insecure, she wanted to blow me all the time, so she could hear compliments about her skills, as well as hearing herself being called Fellatio Jo.
Things changed a week later, when Janice was in the shower and Jo came to me to do a quickie blow job. I came in her mouth before the shower finished, so after swallowing my cum, she looked up at me and said “How about taking care of my cherry later on tonight”? Jo had started going behind Janice’s back to blow me, and I started to feel like we were cheating. I replied “taking your virginity is a serious step and we should talk it over with Janice before doing it”. Jo said “what if Janice doesn’t approve, and I am still stuck being a virgin”? I told her that I couldn’t do it unless Janice agreed, and that was final.
When Janice finished showering and had dressed, she came into the bedroom to see what we were up to. I told her that we were discussing Jo’s virginity, and asked her how she felt about me taking care of it. Janice said “it’s about bloody time. I was starting to wonder if everyone had changed their minds”. Jo gave Janice a hug and thanked her over and over, and then she looked at me and asked when we could do it. I said “my cock is at your disposal, so say the word and it will be done”. Jo asked for one special consideration, and that was to be alone with me. I could tell by Janice’s reaction that she was disappointed to be excluded, so I asked Jo why Janice couldn’t be there. Jo said it was a very personal thing, and she wasn’t comfortable being naked in front of her sister (she didn’t say, but I figured it was because of her weight). I had to protect and preserve my relationship with Janice, so I told Jo that Janice had to be there or I wouldn’t be able to do it. She relented and said that after dark tonight we would turn out the lights and do it.
During the course of the day, Janice and I prepared the bed with a protective cover, to take care of any blood stains, and we bought special lubricant at the drug store, to ensure Jo’s pussy was moist and well lubed for my cock. I hated condoms and refused to use them, so we agreed that I would not cum in Jo to be safe.
Darkness arrived at around 8:30, so we all had a couple of drinks to loosen up, and then headed to the bedroom. We turned out the lights and we all stripped off our clothes and got on the bed. Jo asked if Janice and I could start making out, to get her in the mood, so we decided to sixty nine. Although it was pretty dark, our eyes were adjusting and you could see fairly well. Jo was lying on her back with her head propped on the pillow trying to see what we were doing. The sucking and slurping sounds we were making were turning Jo on, and she started reaching for my balls, as Janice sucked my cock. All of a sudden I had two mouths working on me, so I decided that I had to preserve my boner for Jo’s cherry, and removed myself from the sixty nine. Janice said “it’s time; let’s get Jo lubed up and ready to take your cock”. What happened next surprised the hell out of me. Janice had Jo lie on her back and with the lube bottle in her hand, got between Jo’s legs. I thought she was just going to insert some of the lube, but she actually started licking and sticking her tongue in Jo’s pussy. She did this for a few minutes, and Jo seemed to really like it because she was moaning and squirming around. As Janice inserted the lubricant into Jo’s pussy, she sucked on her clitoris, and Jo screamed that she was about to cum. Janice sucked on that clit with everything she had, and when Jo raised her ass off the bed and let out a loud squeal, we knew she had come.
I was more than ready now, so Janice moved aside and let me between Jo’s legs. As I moved my cock over the outer pussy lips, Jo thrust her hips towards me, trying to impale herself. I eased into her, waiting to feel the hymen blocking my way, but I just kept on sinking until I felt my balls hit the cheeks of her ass. I couldn’t believe it, but there was no cherry, so rather than saying anything, I started thrusting into Jo, and could feel her humping back at me, to take me deep in her pussy. This being Jo’s first fuck, I wanted her to enjoy it, so I tried to go slowly and make it last. Jo was breathing heavily and moaning that she wanted me to fuck her hard and make her cum. Janice had been watching patiently, but she sensed that Jo wanted to cum, so she approached my ass and took hold of my balls, and started whispering words of encouragement to me. Listening to your girlfriend say “fuck her babe, give it to her hard and make her cum”, is a real turn on, so I started with ball slapping deep thrusts, and within a minute Jo started bucking like a wild stallion and screamed she was cumming. I could feel her nails digging into my back, as my balls started releasing my cum, and when she felt the hot streams pulsing deep in her pussy, she lost total control and pissed herself. I don’t think anyone cared, because we were all caught up in the moment. I guess Janice and I should have thought to mention to Jo to empty her bladder before sex, but it just never occurred to us. Janice and I lay with Jo cuddling for a few minutes because I didn’t want her to feel like she had been used. After about ten minutes, we asked Jo to clean up the wet bed, and we went downstairs to get something to drink.
What occurred to Janice and I is that I forgot that I shouldn’t have cum in Jo’s pussy, and now we had something else to worry about for a month. Also, the lack of a cherry really bugged me, but I never told Janice and never brought it up with Jo. Maybe she had used a dildo when she was lonely and depressed, and broke it by accident. It really didn’t matter, because she could now say that she wasn’t a virgin anymore.
Jo didn’t get pregnant, but she did manage to get hooked up with an old friend of her brothers, and we soon found out that he was calling her Fellatio Jo. She wasn’t around much anymore, so when Janice and I talked about her, we referred to her as “the cocksucker”.