Cuckolded on the High Seas
It had all started some years before when I met Liz at University. She was petite, 5ft 5 tall, firm B cups, breasts, great legs, and superb tight arse. She would always wear the shortest skirts or dresses displaying her shapely legs. Her tops always displayed her cleavage, and she had long, very long dark hair and olive skin which would tan brown in little time. Liz was studying to be a teacher, and I was at law school.
I was taller than her but not much taller, and I had a small build, and my whole physique was not much bigger than Liz. I played a fair bit of sport so was fit, and wiry but not muscled.
The engineering students had organized a Roman toga party, and a friend of mine had invited me along. The only rules: wear a toga and bring some alcohol. Engineering students are a fairly wild bunch I quickly learned. Most wore a sheet and little else including the women, and they could drink. I met Liz for the first time at this party. She arrived with her boyfriend. She looked stunning and was turning heads. Her boyfriend was a tall, strongly built guy who I later found out was also studying to be a teacher. His name was David, and he had met Liz at Uni.
Everyone was drinking out of little plastic cups, mainly wine and beer. The party was getting very entertaining with plenty of drinking competitions and plenty of groping. Liz caught my attention. She had a flowing white sheet on which didn’t hide much, high red heels and little else. You could see she had no bra on as her nipples were very visible under the toga, the night is a little chilly. David would put his hand under her toga now and again and touch her arse, and you could clearly see she had a red g-string on to match her shoes.
By this stage, some men were forming human towers and crashing into each other. Others were getting eskies of melted ice and dousing unsuspected women. I was getting hard. I was hoping Liz would be a victim so I could get a better look at her tits.
I had worn some tight-fitting briefs under my toga. I wasn’t hiding much, and on a cold night, it was probably less than 2 inches and not visible. Even at my best, I would grow to just over four inches and not particularly thick. I could see David wasn’t wearing underwear as Liz was often putting her hand under his toga. You could see his cock was flaccid but was clearly visible in shape under his toga. It was making a large, very large bulge under the sheet. I gave thought to its size when it was fully grown.
I think after a while they noticed I was staring at them and they called me over to their group. Liz said, “Hey you seem to have been checking us out so you may as well join us.”
I said, “Sorry I was just admiring how stunning you are. My name is Phil.” We then starting chatting and seemed to click. We talked about our courses and were becoming so pissed I don’t really remember much of our conversation or how I got home.
I do remember that David, who was standing beside me made a point of turning towards me and his cock rubbed against my side. It was semi-hard, and I could feel its size. It may have been an accident, but I think he was telling me that Liz was his girlfriend.
After that night I would see Liz often on campus, and we would have a coffee or a drink together in the afternoon. We enjoyed each other’s company and would make each other laugh. After a while, she said she and David had broken up and did I want to go out and do things together as friends. So we started going as friends.
Even in those early days, it was Liz who made most of the decisions. Where we ate or what band or movie, we saw. We were more like girlfriends, but I was always happy looking at her in her skimpy clothing.
One day we were at a hotel having a drink, and she was wearing the shortest skirt. As we were talking my eyes kept drifting down to her legs which were crossed. She then uncrossed them and parted them just slightly. I then had a clear view of some sheer black panties covering a shaven pubic area. I’m not sure if it was a deliberate act or not, in any event, I started to get instantly hard. As I have said luckily (or unluckily), I’m not large in that area. I must have just kept staring. It was the first time I had seen her pussy. I snapped to attention when Liz said quite loudly, “What are you staring at? It was like when we were at the party when we first met.”
I just stammered that I was only looking at my drink. This excuse was quickly dismissed, “You were looking up my skirt weren’t you. You had better carefully consider your answer, or there may be consequences.”
I decided it would be better to admit it and say sorry which I did. She said, “That’s better. Obviously, you have ideas of being more than just friends.”
I had always wanted to be more than friends but assumed I would be punching above my weight in asking her for a real date. “Liz,” I said, “any man would love to be going out with you as your boyfriend. I never asked as I thought I was out of your league.”
Liz looked at me intently and said, “I didn’t think you were interested in me as a girlfriend. I thought you may bat for the other team. We get on so well I’d love to be your girlfriend.”
I rose and walked around to her and gave her a wonderful kiss which I could tell from her response she enjoyed. I was standing in front of her, and she remained seated when she said, “Someone is pleased to see me. That is a nice little lump in your pants.” She seemed to emphasize the word little, but I didn’t care at that moment.
We then went through the kissing fondling stage. She would play with my cock, and she seemed satisfied with it. I loved fingering her pussy which was very tight and always very wet. I loved taking photos of her in her bikini at the beach. It didn’t hide much. Some shots were of her arse, and others were frontal shots. Many I had zoomed into her breasts and pussy area. I would sticky tape them up in the bathroom and wank over them in the shower every morning.
One day I asked her to my apartment for dinner. I spent the day fixing the place up and cooking the best dinner. I knew she loved garlic prawns and grilled fish. I also knew she became very passionate and frisky after a few glasses of Sauvignon Blanc. I bought 6 bottles and some pisco to make sure.
The buzzer rang, and when she came in, I instantly got hard. She was wearing a tight top and obviously no bra. If the skirt had been any shorter, she would have been arrested for indecent exposure. The tops of her stockings were clearly visible. She wore the highest fuck me boots possible. The dinner went very well, and Liz was becoming quite intoxicated and very flirty. We retired to the lounge to watch a movie, and we were both doing a lot of fondling with our clothes still on. She then went to the bathroom and seemed to be gone a long while so I got up and asked if she was OK. She instantly opened the door. To my shock, I could see she had the photos in her hand. I had put them in the bottom drawer so she wouldn’t see them.
She said quite harshly, “What are these?”
I said they were just some beach photos I took to which she replied, “I can see that. Some are very close-up shots, and many are stained. Why are they in your bathroom with sticky tape? Have you been wanking over them?” She had told me when we started going out that severe consequences would flow if I was truthful with her.
I replied in a trembling voice, “Yes I’m sorry Liz I wank over them every morning in the shower. Some probably have cum stains on them. I think about making love to you while I wank.”
I could tell she was angry. She said firstly that I had not had permission to take such close-up shots. Secondly, she told me I was pretty pathetic to be wanking over them and to follow her. She returned to the lounge and sat with her legs crossed and told me to then stand in front of her. “Strip,” she ordered. I had never been nude in front of her before and was a little slow. “Strip immediately,” she ordered again. I took my shirt off, then my trousers, and I was then left in my male purple-colored bikini briefs. “Underpants as well,” I was told. I then slid them down exposing my semi-erect embarrassed cock. “Hands-on your head and spread your legs,” I was told, and to which I complied.
She commenced talking, “Very good. At least you are compliant with orders. You are looking a little flushed in the face. No wonder after I found your little photo stash. I want you to be silent, and you can listen to me. I’m firstly going to check out your measurements. I can see you have smallish arms and legs. Really more like a girl would have.”
She then uncrossed her legs showing me her sheer lacy black panties. I could feel my cock now getting harder. “Mmmm I can see your little pecker likes me. Turn around so I can see your arse.” I found myself obeying her and becoming very aroused. “Nice tight arse I must say. Now turn back facing me.” As I did so, she gently put a finger under my twitching member, which was now at full mast.
“Is that full length? Let me see.” In saying that she pulled out her phone and placed it on my throbbing dick. “Slightly more than 4 inches and below-average thickness. Unless you are very good, this is going to be a problem. I’ve never had a boyfriend under seven inches, and most have been eight to nine inches at least. As a beta male, you may be in some trouble. Do you think you are up for it, you little wanker?” I was now very nervous and felt very vulnerable but was also so excited that I might fuck Liz.
I replied in an anxious way, “Liz I would love to try and satisfy you as you are the most stunning woman I have seen. I’m so sorry about the photos.”
She studied me and after some time said, “I have strict rules for beta males. The few I have met that I’ve allowed to fuck me must always cum last. All have failed. They get so excited they blow their little loads. The consequence of that is they must clean all the cum. Are you prepared to do that? If you don’t, you won’t see me again.”
I still had a raging hard-on, and she had now spread her legs, so I had a full view of her shaved pussy. I felt like cumming then. “Liz I will do my best as I so want to be inside you. I’ve been dreaming of it. I will promise to clean up if you don’t cum first,” I hastily said. I thought I hope I can last as I hadn’t cum in a few days of wanking and knew I had a bank up of sperm and anyway I could easily clean up. Win-win I was thinking.
She stood and told me to follow her into the bedroom which I did with my hands still on my head. She stood near the bed and pulled her top off. I had fondled her breasts but not seen them fully exposed. They were pert and firm, and her little nipples were hard. My cock was starting to leak some precum. She then pulled her skirt down and was standing only now in high heels, stay-up stockings, and her little lacy panties. I was now dripping onto the carpet. She then slowly, teasingly began to lower her panties exposing her smooth-shaven pubic region and the beginnings of a lovely slit. It was the best sight I had ever seen and had to really restrain myself, so I didn’t orgasm.
She laid down on the bed and spread her gorgeous legs totally displaying her shaven pussy. I could see she was already wet. At that point, I nearly came standing there looking. I was in a trance. I heard her say, “Ok little fella see what you can do.” I crawled onto the bed and put my hands on either side of her and began to slowly lower my cock towards her pussy. I was trying to concentrate on pleasing her and not cum first. My cock head touched her lips, and it was pulsing, and my balls were aching. I gently eased about an inch in when I was betrayed. I could feel it building, and although I tried, it wasn’t going to stop. I thought I might just ease out and relax, but it was too late. I exploded all over her pussy, thighs, and stomach. It just spurted everywhere and then just kept dripping. I hung, my head.
I looked at Liz, and she had a huge grin on her face. I was disappointed but what a great cum. I had just exploded, and certainly, it had been better than wanking. I was about to get off the bed to get a towel to clean up when she said, “Where are you going. I told you there were consequences if that happened. I hope you enjoyed yourself. I got one inch for about one second.” I was a little confused and still in the afterglow and said I was getting a towel to clean up. Now she laughed and said I didn’t need a towel to clean up I just needed my tongue and mouth.
I was still in a haze but was now quickly realizing what I was required to do. I had never eaten my cum before and now was faced with eating loads of it. Liz was now beaming. She loved my predicament. I had agreed to clean up, or I wouldn’t see her again. She said, “Clean the sheets, then my stomach and legs, and finish with my pussy.” I began licking. It was salty but not as bad as I thought. I licked the sheets than her stomach. I enjoyed licking her skin. Then onto her thighs and finally her pussy. I now had my tongue and mouth on her pussy and was starting to enjoy myself. I licked and swallowed, and I could tell she was getting aroused. Even though I had cleaned up all hints of cum, I kept going. I felt her hand rest on the back of my head pushing me deeper. I’m not sure how long I licked and sucked but could feel her thighs tightening around me as she exploded into wave after wave of thrusting. I could hear her now moaning and repeating, “Oh fuck yeah.”
She eventually released my head from her thigh vice, and I could breathe again. I rolled away and just lay there as I could hear her breathing heavily. I felt very content even though I had failed my test. Liz began to stir and ordered, “I need a drink now thank you. A pisco sour would hit the spot.”
I began to move and slowly headed into the kitchen to make the cocktail she had ordered. I saw Liz emerge and sit again in the lounge room again fully clothed in what she was nearly wearing. I was a little disappointed at her clothed again but took her the best pisco I could make.
I stood to wait for an order. I seemed to be now waiting for instructions from a woman who seemed so dominant. She told me to get myself a drink and sit down with her which I did as quickly as I could. I sat next to her still naked and waited for my next order.
Here I was with my girlfriend in my lounge totally naked with her fully clothed, albeit showing a lot of leg and cleavage. It would be very clear to anyone observing who was the dominant party. She commenced, “Phil, firstly that cum I had on your tongue was fantastic. So you make good liquor, and you are a good licker. That is a good combo. Also, you are very obedient which I like. Although you hesitated somewhat, you did clean up all your mess in the correct manner. I’ve always been a dominant person and have never really enjoyed being with men who want to be dominant and order me around so I can see the positives in our being together.” She took a sip of pisco and paused obviously contemplating her next statement. I was quite anxious. “Of course what is of concern is your dick and its performance which could only be described as abysmal. I have never dated anyone with a cock that size. It is simply inadequate for my needs unless you can demonstrate otherwise. My initial thoughts were to end our relationship now, but I have reconsidered those thoughts. You in all other ways are just the best boyfriend I have had. I can see we may be able to make it work.”
I was now becoming relieved that I might see her again. I said, “Oh Liz that would make me so happy.”
She replied, “Well before you become too happy I will be setting down some conditions which you can accept, or we walk away. Ok?” I already knew one condition which was to lick up my cum if I came first so was a little afraid of further conditions.
“Firstly,” she spoke in a stern way, “if I tell you to do something you will do it. I will never ask you to do anything dangerous, or that may affect your reputation with your family or straight friends.” I was a little confused by that statement as I only had straight friends, so I wasn’t sure who these other friends were. “Secondly you will be punished at my discretion for any disobedience of orders or incompetence, which would include you cumming first. Yes, licking up is a rule, but there will also be discipline involved. Do you understand?”
I had only been disciplined by my parents or teachers so I was a little shocked to hear my girlfriend would be doing that and said, “Liz what sort of discipline do you mean?”
She sighed, “And I wish to impose. It may entail you standing in a corner for a while to reflect on your behavior. It may involve some physical pain such as smacking. It will always be to improve your behavior. I hope you understand that and when I ask you a question I want an instant response otherwise there will also be punishment. If I ask you to do something I want an instant response. Do you understand?”
I must have sat there just thinking. I was becoming overwhelmed with ideas and behavior I had never heard of in a relationship. I quickly came to my senses when she said in an abrupt and loud voice, “Right. It seems you want some discipline. I expected an answer immediately. As well you came first earlier. You can get over my knee now with your arse in the air for a spanking!”
I was in a state of shock that my girlfriend was going to spank me over her knee. I just sat there. “Every second you delay will be more smacks, so if I was you I’d get you pathetic little dick on my lap and present your arse!”
I had now woken from my daze and rose from the lounge and placed myself over her lap. It was more embarrassing than eating my cum. I didn’t want to lose Liz, so I complied. She smacked her hand loudly down on my right cheek, and a crack went through the air. It hurt, and I whimpered, “Ow that hurt.”
She replied, “Don’t be such a wimp and start counting the snacks out loud. Any more complaints and I’ll double the punishment.” So I started counting the spanks and made no further complaints, and at ten she stopped. My arse was on fire and on the tenth smack I let out a little whimper.
“Get up and go stand in the corner hands on your head. You cry like a little girl.” I trudged to the corner rubbing my arse which must have been very red and then put my hands on my head. “Spread your legs as well,” she ordered, and I again felt very humiliated.
I remained in the corner for some time and could feel her eyes staring at my arse. Finally, she told me to get her wine and come back and stand in front of her. I quickly went to the kitchen and poured wine and then took it to her and stood in front of her. She looked pleased. I stood there for some time with her drinking with one hand and fondling my balls and dick with the other. She then spoke, “It has been an entertaining night for me and an educational night for your it seems. I really enjoyed myself. There a couple of more rules, however. I will own your little cock and balls and within reason do as I like with them. The final rule for tonight, as I imagine your head is spinning, is you will call me Miss when we are alone or with special friends. I have down some reading of a number of female-dom articles, one in particular by Mistress Amber, and it just reinforces who the boss is. Do you understand?” I now knew to answer instantly and said, “Yes Liz.” She smiled and said, “Very quick answer but try again. It is Miss.”
“Yes Miss,” I blurted.
“Good boy or maybe in your case it should be ‘good girl.’ What do you think?”
Without thinking, I heard myself saying, “Yes Miss.”
With that, she rose and gave me a passionate kiss while holding quite tightly my balls. I started to get aroused again. “Not now little fella I’m tired and getting a cab home. I’ll talk to you tomorrow,” and she proceeded to go. My cock started to grow as she waltzed to the door swinging her sexy hips in her little skirt.
I simply said, “Yes Miss have a good night” and she was gone.
I went straight to the bathroom, retrieved my photos from the bottom drawer, hopped into the shower and started to give my dick a really good clean.
I stayed awake for a long while that night. It had not turned out as I expected but I felt really content. Had I enjoyed myself because I’m naturally submissive. I had never thought I had been but tonight had been turned on by being controlled by a dominant woman. I knew the only way I could stay with Liz or Miss would be to accept she was in charge. I knew none of my friends would accept that. Obviously, I was different. I finally fell asleep having decided to be the best I could at pleasing Miss.
Our relationship continued for many months. I continued to cum first. I continued to eat my cum. Miss continued to cum on my tongue. She now liked sitting on my face and would cum grinding on my mouth and tongue. I occasionally would penetrate her with my cock for longer than a few seconds but never long enough to make her cum. She told me often she doubted I would ever make her cum with my dick.
After a while, I would rarely be allowed to fuck her. Then one day while I was on my knees licking her as she was about to cum saying, “Oh fuck yeah, keep licking, your tongue is so much better than your clit,” she exploded in a violent orgasm, her juices exploding everywhere. We both collapsed, but I was in a state of shock with her saying I had a clit. After I let her luxuriate in her afterglow, I asked her about that remark.
She took a little while to speak, “I’ve been thinking about your continued lack of ability with your dick. I have allowed quite some time for you to perform but as you know, it hasn’t happened. Any man would be ashamed, but you don’t seem to be. I’ve decided from now on that what you in fact have is a clit. We make love like two women. We really are like lovers in an all-female relationship.”
I was still exhausted after licking her. I was trying to take in what she was saying, and it did make sense. She only came when I licked or fingered her. I did cum in her pussy, but she would be more satisfied and cum if I used a dildo or vibrator on her. I had more satisfying orgasms in the shower playing with myself or Miss giving me handjobs. She called them finger jobs as she only used her thumb and a finger to get me off and that only men with proper dicks got handjobs.
I gave in. “I suppose you are right when you think about it. We do make love like two women. I hadn’t really thought about it in those terms. I suppose it makes no difference what it is called.”
Her reply rocked me, “I’m sorry Phil, but it has massive consequences. The reading I have done is that once it becomes a clit, it should be in panties, not your boy briefs. A further rule is to be added from today in that you will now only wear panties and g-strings. You will put all your boy briefs in the rubbish. Lucky for you I have done some shopping and left a bag for you in your bedroom. Once you have disposed of all that useless boy underwear, you will select and put on something from the bag. You will then come out and stand in front of me with your hands behind your back. Ok?” My head was spinning again surely she wasn’t serious, but I didn’t want a sore arse and said yes Miss immediately and proceeded to the bedroom.
I was trembling that I would soon be wearing panties in front of my girlfriend. I thought of turning around, but knew I would be finished with Liz who was now Miss. I gave in and accepted my fate. I went to my underwear drawer and took all my briefs out. I thought of keeping one but fearing the consequences took them all and threw them in the rubbish. I returned and saw the bag, picked it up, and tipped the contents out onto the bed. Out tumbled panties and g-strings. Some black but mainly pink in color. All had some lace or bows or both. I counted seven pairs which I presumed was one for each day of the week.
I decided to choose black panties. They only had pink lace on the edges and pulled them up my legs and looked in the mirror. There I was my image staring at me wearing panties. Never did I think I would ever be wearing panties. Now I had to walk back into the lounge room and show my girlfriend. I slowly walked in stood in front of her with my hands behind my back.
“They are so pretty,” she cooed. “What a great pick. They are so you. Turn around so I can see your arse.” I turned and was greeted with laughter, “Oh they look so natural on you. Our special friends will love them. So silky they must feel sooooo nice?” When she said that I realized they felt very nice over my cock, sorry my clit as I was now to call it. As I started to get hard, she smiled and said, “That is so cute. Your clit is so excited it is getting hard. If you are a good girl, we can give each other a fingering.”
“I have decided on one more rule today which really just matches your panties. A man doesn’t wear panties. Your wearing of panties and having a clit really say loudly you a girl, and Phil is not really a girl’s name you’d agree?”
I knew another shock was coming and could only muster a, “I suppose so Miss.”
She responded kindly, “Look I know it is a huge change, but I’m sure you’ll come to your girl name you will still be Phil with our straight friends, but with our special friends and me, I have decided you will be Philippa. I think it is a lovely feminine name for you. I’m sure you will come to embrace it. Now I’d like you to thank me Philippa for your new name.”
I was now rocked to the core being in panties and with a girl name. I spluttered, “Yes thank you oh so much Miss for my panties and my new name Philippa. I so love my new name much more fitting than Phil. You are so kind.”
She just smiled and said, “It is so much easier accepting it rather than fighting against it. You look so pretty. I can’t wait till we get you some skirts and other girly things to compliment your panties. Now off you wiggle and get me a nice drink, Philippa.
I could only reply, “Yes Miss,” as I scurried into the kitchen.
More months went by, and we became really loving girlfriends. I had accepted my role as a girl. It was easier than fighting against it. Miss had made further rules, and I was now always fully shaved with smooth skin from the neck down. I now had a wardrobe of skirts, dresses, stockings, high heels, padded bras, and even a corset to make me more shapely. On occasions, she would apply makeup and a wig, and I would make and serve her dinner as a maid. She even ordered me to grow my hair to make me look more girly.
I decided to take a chance. I had been thinking for some time I would love to marry Miss and be her submissive husband forever. I had now totally accepted and embraced my role as her submissive girl. We still lived separately, and I really wanted to live together as a man and wife in public and as a girl in private. I bought a ring to propose and arranged a dinner at an exclusive restaurant. I hired a limo to pick us up and take us there. I wore a suit with panties and stockings underneath. She wore a very short black skirt, black stockings, black boots, and a lacy see-through top.
She looked drop-dead gorgeous and very dominant. Miss had ordered some expensive wine, and after a few glasses, I decided the time was right. I dropped to my knees and proposed. I could tell by her expression of surprise she had not expected it. I asked her to marry me, and she seemed very happy. I showed her the ring and waited for her response. It seemed like hours till she spoke, “What a beautiful surprise. I wondered what all the fuss was tonight. Yes, I would love to marry you, but it would be with you agreeing to very strict conditions.” I was in raptures as she said yes but concerned regarding it being on certain terms. I knew her terms usually involved me being very submissive and humiliated.
I was told to sit back down, and she would explain. I did so, and she continued, “Well there will need to be some new rules. Firstly you will not be putting your clit in my pussy again. It has not satisfied me once. Also when I have stayed with you overnight, you have put it between my thighs for a little rub. That is annoying and pathetic and affects my sleep. You also still masturbate over my photos. Again pathetic. So not only won’t you be getting pussy with your clit, you won’t be getting thigh rubs or fingering either because you will be clit caged!” As I listened, I struggled to cope. She had told me previously about cock cages but never really thought much about it. I was getting married but was not going to enjoy her pussy as all husbands would do. I was not even going to enjoy my thigh rubs again or fingering. I was struggling to comprehend the severity of this and took another large swig of wine to kill the pain.
Worse conditions were to come if that is possible. I was then told, “I however still need to be satisfied by a real cock. A woman has needs that you can’t provide. I will have lovers with the proper equipment to take care of my pussy. I will always, however, allow you to listen or watch when I’m being fucked by one of my lovers. Not only that as you clean up your cum, you will be required to clean up their cum not only from my pussy but from their man cocks.”
I threw down another wine. Did I want to proceed with such conditions? I was shocked by this last condition. Maybe she would change her mind later. This marriage proposal was not proceeding as I expected. I was getting a little tipsy, and I just wanted to get married no matter what so taking another gulp of wine I said, “Yes Miss I understand and accept your conditions.”
“Good girl. I knew you would. You can kiss me to seal the deal.” I got up to kiss her, but she said, “No get on your knees under the table and kiss your Mistress’s pussy.” We were in a full restaurant but thought I could pretend to be retrieving a dropped knife or fork so dropped under the table. Miss had her legs apart, and I could see she had no panties on. I pushed my head between her legs and kissed and licked her wet pussy. She clamped my head to show she was in charge then released me. I sat back in my chair relieved and happy we were now engaged.
We raised our glasses to each other with cheers when she said there was one further condition. I couldn’t comprehend what any further conditions could be. She started, “I will make all the wedding arrangements. It may not be a traditional wedding.” Well given events so far I wasn’t at all surprised at that statement. If I knew then how the wedding was going to be conducted, I might have called it quits.