Daddy, Boyfriend & Me: Her First Romantic Menage

by S. L. Finlay

  “Of course. Isn’t it better to know everything, then you can do more with what you do know?” He asked.

  “What do you mean?” I asked.

  “Well, if I know that you like flowers, then I can get you some flowers when I want to make you happy, or if I need to apologize for doing something wrong. But,if I know that you like flowers, and that the reason you like them is because you like the way they make your home smell, I can get you flowers that have a nice scent, and know that you’ll like them better. Or maybe I can buy something else that smells and looks nice and when I give it to you, I can tell you why I got you that and not flowers, for example.”

  “So, basically, you’d be buying me toilet spray to save money?” I teased, giggling.

  William wasn’t going to let me have that joke, he shook his head slightly while smiling. “No. That’s why I would buy you a teddy bear that had a scent. It would make your house smell nice, but it would also be something you could keep and think of me when you cuddled it.” He told me.

  “Oh,” I said, surprised by his idea and actually kind of happy about it, “so I could cuddle the bear while you were away on business, for example?” I asked.

  William gave a little nod, “you could, if you weren’t away with me.”

  It took me a moment to realize what he had just said, “what do you mean if I am away with you? Am I supposed to be going on business trips?” I asked.

  “Well, you are my PA. So if I needed you, you would be coming.” He told me.

  “But I am your part-time PA, wouldn’t you want to take-” I began, but William cut me off with a shake of his head.

  “-I would be taking you because I wanted to be with you, not as my PA. But, on the books you would be my PA.” He told me.

  I thought about what he had said and it struck me all at once, “did I only get this job for that reason?” I asked, quickly feeling deflated.

  “What?” William asked, breaking from his relaxed self for a second, “no! Of course not! I would never - you don’t honesty think that, do you?”

  Watching his reaction, I knew he wasn’t lying.

  “I’m sorry. No, I didn’t think that.” I told him honestly, because before a few moments ago when I had asked the question, it had never occurred to me that I got the job because William fancied me. I thought he had given me the job as a favor to my family without actually calling it such. That and the fact he knew I wasn’t going to die without the income if they had to cut back my hours or lay me off, something I doubted the firm would do as they could afford their PAs and other office staff without any issues.

  “Are you sure?” He asked, “Because if you think that, or are only here because you’re worried about losing your job, I want to tell you right now that’s not the case. You can leave now without-” He seemed to be working himself up, so I put my hand up in a ‘stop’ motion and interrupted him, cutting him off.

  “-No.” I said, “that’s not the problem. I don’t think that at all, and I would never think such a thing of you.”

  William let out a long breath he must have been holding on to, and his shoulders which I hadn’t noticed were raised to begin with dropped. I felt immediately guilty for having made him feel uncomfortable.

  “I’m sorry.” I rushed, “I don’t wand you to think I…” I began, but didn’t know quite where to go with that.

  William picked up what I had said, “I wouldn’t want you to feel uncomfortable. I know there can be consequences for male bosses who make a move on their PAs, but I don’t care about that. I care about making you happy. That’s what’s motivating me right now.”

  I nodded, I believed him. He seemed so genuine. Of course that’s what he cared about. When I thought back, I couldn’t really remember a time when I knew William and I didn’t think he had a bit of a crush on me. The thought made me smile. I wanted to ask him about it, but the food arrived and as we ate, the conversation seemed to move in a different direction.

  We talked about random things again, with William keen to know what felt like every little thing about me. He had a lot of questions, and I was happy to answer them, although I was surprised every time he would get an answer and be super interested.

  With Joel, we were discovering one another in a different way. It was less inhibited. Because of this, I never got these types of reactions from Joel when we were getting to know one another. There had never been a wall between us, placed there because of external expectations and the belief on either side that we should behave a certain way in any given social situation. We were free to do as we liked from the start. Having to break down walls though takes time. Time and energy you can expend in other more fun ways at the start of something new.

  Although it felt easier with Joel in the short term, I felt that William having to wait in the longer term meant that he was more committed by the time we got to the dating stage, which felt a little odd. A first date when you already knew each other for so long was so different to what I was used to, and I thought I liked it.

  This same mood continued on through our meal and dessert. It wasn’t until we were drinking more wine after dessert that I realized I hadn’t told him about Joel yet, and about how this was really okay. At what stage do you tell someone you’re on a first date with that you’re actually seeing someone else and that yeah, it’s cool to see them both at the same time, not to worry one little bit about that.

  I was sure I was telling him this now in part because of the wine we were drinking, but also because I had been drinking this whole time. As I wasn’t driving, I had had fairly liberal amounts of wine and was feeling pretty happy.

  As I sipped the after dinner, after drinks wine I asked William after a poorly timed hiccup, “is there anyone else you’re seeing right now?”

  William gave me a little smile before saying, “no. Just you.”

  “I am seeing someone else.” I told him, “but he knows about this, and is cool with it.”

  “Right, yeah.” William said, nodding his head in a way that someone who is only on their first date with you should.

  “No, I mean, he and I are sort of an item, and he told me it would be alright if I had a second boyfriend.” I told William.

  William raised an eyebrow at me and told me, “that’s interesting.”

  “Is it?” I asked.

  “Yes. I had never heard that one before.” He said before seeming to consider something for a moment and asking, “are all the young people doing that now?”

  I laughed, “I don’t know about other young people.” I told him, “I just know about me, and this is something I would like to have in my life.”

  “Multiple boyfriends?” William asked.

  “Yes.” I said honestly and confidently, “I would like to be adored by several men, yes.”

  William gave me a big smile then, he got it.

  “When I was living in New York,” He began, “I was seeing a woman and she and I met this other couple. Together, we all had sex. It was sort of like swinging, but, more intimate. Anyway, so we had sex that one time then we kept seeing one another. It was like a, four-way relationship.” William said, and his use of the words ‘four way relationship’ was actually kind of comforting. It wasn’t just me who didn’t have a name for these sorts of arrangements I was happy to see.

  “Really?” I asked, “what happened?”

  “Well, I had to come back to Australia.” He told me.

  “Oh.” I said feeling like his end was both anticlimactic and a little sad, “I’m sorry.”

  “No, no, don’t be.” He told me, “it was a great time, and I was very lucky to have those three beautiful people in my life.”

  “Fair enough.” I said, feeling pretty confident that he would ‘get it’ at this stage, then he told me something that utterly stopped me in my tracks.

  “If I can give you advice, I would say don’t ever let it go like I did. I let that relationship go and I know I will never get it back, or anything quite like it
again. When you find something that makes you that happy, never let it go.” He told me, his eyes watering just a little as he held my eyes with his.

  Looking him in the eye right then, I could feel it. He was right, when you had something wonderful, you shouldn’t just let it slip through your fingers. You should cherish it and nurture it.

  I didn’t want to be passing his advice on to a fellow traveler later, so in that moment I nodded along right as I thought about all that I had - and all that I was about to have - and how I didn’t want to let it go, ever.

  CHAPTER NINE

  Just like I hadn’t been able to believe just how well our date had flowed, I also couldn’t really believe how well our after-date had flowed.

  William seemed to be not only okay with my unusual relationship preferences, but he seemed happy to embrace them. He was just as happy as Joel was, which seemed too good to be true, but which I was happy to embrace. William seemed happy to embrace things that were a little left of center generally, which surprised me greatly as I had never thought straight-laced William would pursue such alternative lifestyles. I also never would have guessed that he had done so before and wanted to do similar again. This was something which felt really out of left field for me now. His acceptance and willingness to embrace these types of lifestyle choices not only surprised me, but actually left me feeling like I had been really wrong about him, even more wrong than I had been when I decided that Joel wouldn’t be okay with sharing me only to find out later that he was not only okay with it, but happy with such an arrangement.

  When William took me home, I invited William in for a night cap. I knew from all my old movies that he would know what this meant. Even though I hadn’t been on a lot of dates with a lot of men - my generation doesn’t seem to date as much as people did in the past - I knew this move.

  William seemed to hesitate, but only for half a second.

  “Sure, I’ll come in.” He told me in the end and we shared a smile before I unbuttoned my seat belt and we headed for my front door together.

  I felt nervous as hell, even after all the wine. I had liked William for such a long time but had told myself again and again how this wouldn’t work. I had told myself how I couldn’t have this type of relationship with him because he was ‘too old’ for me. I had ruled him out because he didn’t fit some ideal I didn’t agree with and an ideal I had no idea where I had picked up or why I had held onto it for so long. Now that I could have any man I wanted though without needing them to fit some limiting - and limited - ideal, things felt different. I felt assured that not only could this work, but it could work even better than a regular couple did.

  We walked in the front door of my house and I turned towards my kitchen to see what bottles I would have laying around which I could offer William, but then he grabbed my hand and squeezed, which made me turn towards him and then he had me.

  William was kissing my lips, stealing a little kiss which then grew as I moved towards him. Our bodies felt like magnets drawing in closer to one another, and my heart felt like it was leaping out of my chest just to get close to this man.

  His hands were on my body and everywhere they touched, it was like he left a fire behind on my skin. The heat between our bodies was immense. I quickly led him into my bedroom and pulled him with me onto the bed. We fell onto the bed together a little awkwardly but I didn’t have time to recover from the giggles before he was kissing all my giggles away.

  It was hot, but there was something else there too. This longing that I hadn’t been aware he had shared. This deep desire to be close, to get closer. To feel his body against mine and have him in this way, this intimate way that I had only just begun to let myself believe could happen. That I had only just recently given myself permission to let happen.

  Now I had given myself permission though, that feeling of surrender, of letting my walls come down was growing with every single kiss, and every single touch.

  I sighed into his lips as William started to take off my clothes.

  “What?” He asked, his voice a little shocked. “Are you okay? Are you sure you want to do this?”

  “Oh god yes!” I told him, “I need this so bad!”

  William held my gaze for a moment, his face only inches from mine before he gave me a wicked grin and told me, “me too!”

  Then it was on. My clothes were by the bed discarded in a mess with his clothes, and he was pulling me on top of him. Even as I was on top of him, I felt like he was very much in control. Our kisses intermingled as he positioned me over his hard cock and pulled me down onto him.

  As he entered me, we were kissing and the feeling of his fat cock stretching me out as he pushed into me was enough to make me moan into his lips. Together we moved at a slow speed, as if William was drawing out the pleasure for the two of us. Pulling away from our kiss I stayed close to his body, making a point of gazing into his eyes as we touched and kissed. Making a point of giving him small kisses between my deep moans.

  “That’s good for you, isn’t it?” William asked from under me and I moaned a little as he thrusted as if to make a point.

  “Yes. William, that’s Amazing!” I said through moans, “oh god yes!”

  “What’s that girl, I can’t hear you?” He asked me.

  As I was answering him, he was thrusting harder into me, hitting every sensitive spot inside me as he did so. I moaned louder and harder as I answered him this time.

  “God yes, oh that feels so good!” I moaned, unable to control the volume of my voice.

  “I’m glad.” He finally said from under me before a seriously wicked grin took over his face and he commanded me, “call me daddy.”

  I stared down at him for a moment before I asked, “Daddy?”

  William’s answering wicked grin, and the rush of blood to my pussy were enough to convince me that this was a good idea.

  “Oh, daddy, that feels amazing!” I told him, feeling much less self conscious than I had the first time I had said it.

  He kissed me and I moaned the word ‘daddy’ into his mouth before pulling away and asking, “Daddy, will you be on top?”

  The question wasn’t just an excuse to use the word ‘daddy’ again, as by the third time I was well used to saying it. I was asking because I felt like it would be more appropriate for the person who really was in control to be on top.

  William gave me a little smile and without pulling out of me, he flipped me onto my back and got on top of me. In no time at all, he had started fucking me hard. Under him, I lost control. I went from barley being able to control myself and being able to speak to a state where not only could I not speak, but I couldn’t stop myself from making loud moans either. It was like all the stored up feelings I had for William were escaping my body now and the Ecstasy of it was driving me so hard I had no control anymore.

  Then I felt it, the familiar build up of a pending orgasm. Usually when I got that sense during sex, I would be excited. I was about to ride the wave, I was about to get the thing I had been so hungry for. But right now, the last thing on my mind was having an orgasm. I almost didn’t want it, because I was enjoying the act so much and felt concerned that if I came, it would be like giving him permission to cum, and then this would be over and I didn’t want it to end. The sex was great, but this new joy - of calling a man I was so hot over daddy while he fucked me - was something new, and something I didn’t want to end. Not so soon.

  But I couldn’t help it. He was in control, and he was giving me exactly what I needed in order to cum, moving his body so his cock would stroke and press into all the sensitive parts inside me. He was fucking the orgasm right out of me, and I was powerless to stop it.

  As I felt the start of my orgasm, the first few strong convulsions that felt like explosions, William pushed his cock all the way inside me and kissed me. Under him, it was all I could do to kiss him back as the pleasure gripped my whole body. I had no control now over the sounds I was making and my loud moans had become guttural.
I moaned into his kisses and as I was starting to come down from the first few pulses of my orgasm he pulled away and resting on his elbows with his cock still buried inside me he watched as I moaned under him and I tried to maintain eye contact. The eye contact just made this all the more intense as I tried to give him a reassuring smile and had him give me a wicked grin right back.

  When my orgasm was over, I lay there under him, neither of us moving as he played with my hair.

  When I could speak I asked him, “but you haven’t cum?”

  William gave me a smile filled with warmth as he told me, “no, I haven’t cum yet. I wanted you to fully enjoy that first.”

  I nodded from under him and asked, “so, you want to cum now?”

  William was shaking his head at me as he told me, “no. I don’t want to cum yet. I want you to enjoy your afterglow.”

  I must have given William an odd look because he told me, “a gentleman can wait.” Before planting more kisses on me. His care for my enjoyment turned me on and I kissed him right back. His kisses were bringing me back after my orgasm and it wasn’t long before I pulled away after he had been kissing me for a while and asked, “but you want to cum, right?”

  Daddy chuckled. “Of course.”

  “Where do you want to cum? How?” I asked.

  A confused look from him, questioning.

  “What I mean is, do you want to cum inside me? On my body? In my mouth?” I asked the last part with a little excitement. The thought of William cumming in my mouth was a naughty one. I had always been turned on by people cumming in my mouth because it seemed like such a slutty and dirty act, but this respectable man doing something so naughty, well, that was something else!