A Weekend Fling

I was 44. Mike and I had been married for 20 years and the kids were all teenagers by then. I had to go to a weekend conference on a new curriculum for teaching English. So off I went on a Friday evening kissing goodbye to my husband and making sure I packed Bob to take with me. The venue was only 100 miles away, so I was there in time for dinner and reception at 8pm. I sat on a table with 5 women and 2 men (women always outnumber men at education events). After listening to the opening address and chatting over dinner, I went to the bar with 2 of the women and we talked about schools, kids and government interference (otherwise known as Education Policy). One woman left, leaving me alone with Megan. She was 36, from Wales which was a lot further than I had come.

Once we were alone the conversation turned more personal and we both spoke about our home lives. Megan was single having separated from her husband. I told her about Mike and the kids and family life, and we really relaxed in each other’s company. After a few drinks we both decided it was time for bed with a long all-day session ahead. I joked about how different it would be sleeping on my own and then realised that was very insensitive of me, as she was now getting used to being alone every night. I apologised immediately and she smiled and said it was fine. Then she said, “Don’t worry, I came prepared,” and winked at me. I laughed and told her Bob would take care of me too! 

When I got back to my room, I called Mike for a little tease while Bob did his thing, just to let him know I was thinking of him while I was cumming. I also mentioned Megan and told him about our joke as we said good night. He just laughed and said, “Go on then. I can tell you fancy her.”  I just said, “Thank you my darling, “and let Bob finish me off so he could hear me before hanging up. Now I had permission, I hatched a plan to get Megan into my bed the following night.

I found Megan again at breakfast and we carried on where we left off chatting away. Just before our first conference session I leaned over and whispered, “Did Bob do a good job for you last night?” Megan blushed but nodded her approval! The next few hours went by in the usual manner. Lecture followed by questions and answers, and we broke for lunch. I couldn’t find Megan in the crowd but found her later in the afternoon for our last session of the day. I asked her if she had any plans for the evening and she said no, so I suggested we dine together, and it was agreed to meet at 7pm in the restaurant. I made an effort to dress as elegantly as my small suitcase would allow but made sure I found a nice matching set of bra and panties. 

When I got downstairs, I saw Megan dressed in a lovely long blue dress, so I was pleased that she had made the effort too. I confess I had planned the conversation strategy from my side so all it needed was for her to follow the leads. If she veered away and changed the subject, I would be sure she wasn’t interested in where I was trying to go! 

So, I started by asking her how she was coping after her split and that led on to her future plans, of which she was still unsure. So, I took her back to before her relationship and asked about her previous life and her time at university (hoping she might have some tales similar to mine). She gave me enough encouragement to carry on with my plan, so I introduced my bisexuality into the conversation with a story about a girl I dated. She said nothing at first but when I had finished, she asked if my husband knew. I was happy to tell her he knew and had no objections as he accepted it was part of my sexuality. Then Megan surprised and delighted me by admitting she had “fooled around“ with a couple of girls at school. Now I knew my chances of bedding her had improved. I told her more about my bi adventures and how Mike didn’t mind, especially if I ask his permission to play. 

There was no indication from Megan that she was interested in me, but we were enjoying our evening, and the meal and drinks were delicious, so we headed for the bar. We saw plenty of other conference attendees and some were clearly flirting and hoping to get lucky that night. So was I. 

I decided to get the conversation back to my agenda. I pointed out the flirting couples and joked that they would soon be enjoying themselves between the sheets. I said she should dump me and pick up her choice of men hanging around the bar, but she laughed and said she had had enough of chancers and losers and Bob was more reliable. I wholeheartedly agreed but, feeling bolder I asked her what she missed most about real physical sex. She thought about it briefly then said that the intimacy of being held tightly afterwards in that post orgasm glow and going to sleep spooning was one of the nicest feelings in the world. I couldn’t agree more! We were really getting closer, and I could tell that she was now getting emotional, so I reached over and held her hand. She didn’t respond except to leave my hand in hers and look at me and smile. I asked her the question I had been waiting for all day. “Would you like to cuddle up to me tonight? Sex is optional but cuddles would be most welcome if you want it as much as I do”.

Megan never actually answered my question. She simply stood up and walked out of the bar, looking back to make sure I was following. Of course, I was. When I caught up, she was already in the lift pressing the button for our floor. Considering it was my plan to bed her, she seemed to have embraced the idea very quickly! She went to her room first promising to join me shortly. I quickly tidied up my mess and within a couple of minutes she joined me. She came up to me and said, “I will take the optional sex as well as the cuddles after,” and then she leaned in for our first kiss which was soft and wet, much like my pussy. She threw something on the bed. It was her Bob which was much larger than my little clit teaser! We both started undressing. She was wearing a matching set of blue underwear which looked fabulous on her. I ran my hands all over her body and pressed in behind her kissing her hair and cupping her boobs. She moaned and took deep breaths as I unfastened her bra and slipped my hands underneath to play with her nipples and made her gasp. I moved my right hand down and cupped her pussy, feeling the dampness in her panties. I slid them aside and worked two fingers into her wetness and she began squirming in my arms. 

We moved to the bed and fell on each other hands everywhere. She took my panties off and I removed hers and we were naked together on the bed. Then it seemed to be a race to make each other cum. Both fingering each other furiously, kissing, nipple pinching and nipping. I won the race. It was so arousing having her cum hard on my fingers and gasp. She went limp and I was so close myself that I had to finish myself off kneeling over her. Then came the moment she had wanted. We spooned. Stroking each other with our wet fingers, both satisfied, both happy. We pulled the covers over us kissed and snuggled up as close as possible. 

At some point in the night, I became aware of a very light and gentle feeling in my boobs, and I opened my sleepy eyes to find Megan licking and sucking on them. The urgency of our sexual need a few hours before came back to me slowly and I held her head to me and let her enjoy me. Soon we were both fully awake and taking about the fun we had. The need was rising again but less urgent this time. More slow and sensual touching and kissing. I saw Megan reach over her side of the bed and grab her vibe. It was about 8 inches and slightly curved. Soon she was teasing my nipples with it which sent shivers through me, and I rolled on my back and opened my legs and asked her to fuck me slowly with it. She used the tip of it on my clit which almost had me jumping off the bed before sliding it all the way in and turning it down low. It was just what I needed. Not intense, just enough to keep me simmering nicely in my still drowsy state. I wanted more of her so I asked her to kneel over my face so I could lick her and taste her. I think it made her nervous because she seemed hesitant at first but then she settled down and allowed my tongue to explore her. She reached back and turned up the vibe and began to fuck me with it and soon I was bucking hard beneath her as my orgasm built. I went for her clit and flicked it hard with my tongue, then reached up and fingered her at the same time. This time it was me who peaked first, contracting round the vibe, followed by Megan working herself against my mouth and covering my face with her cum while gripping the headboard and squealing in delight. Eventually she climbed off me and it was cuddling time again while she kissed me and cleaned my face. 

The next thing I was aware of was the alarm clock ringing and seeing Megan coming out of the shower. It took me ages to come round, I am not a morning person at the best of times and after a night of several orgasms it is hopeless. Megan dressed, came over and kissed me and told me she was going back to her room to pack up and she would see me at breakfast. I dozed for another half an hour then finally got myself organised and went down to reception to check out.  

Sure, enough Megan showed up at breakfast and just winked and thanked me for a wonderful night. Then it was back to business for the final conference session, and we had coffee together before heading home. We exchanged telephone numbers but there was no promise of any further contact. Just an unspoken understanding that we had both shared something special for one night only. 

I kissed her goodbye and thanked her again then drove back home. 

When I got in. My husband was waiting with a bottle of wine and inquisitive look in his eyes! All he said was, “You didn’t call last night so I assumed you were busy.” I told him my plan had worked and that I had a very enjoyable experience! After dinner, we went to bed early and, while I sat impaled on his rock-hard cock, slowly riding him, I described every detail of my night with Megan until he finally groaned and filled me with his love juice.