Gail Entertains Leo

Couldn’t you just walk away, I asked.

“It wasn’t that easy… I didn’t want a scene, he held me tightly.” Gail’s voice quieted, “Then Leo came over.”

“Who is Leo,” I asked. .”

“Oh, ” she said, too nonchalantly, “The older man. The tall redheaded man.”

“Yes, I’ve seen him watching you,” I said, “Did he help you?”

“He must have seen what was going on. He came up to us on the dance floor and just took hold of my right arm, he leaned close to Patricio and said something, then danced away with me.” Gail laughed, obviously replaying the scene in her mind, “Actually, it was pretty smooth.”

“Why do I seem to remember him from somewhere?” I asked. Gail, now back at the bathroom mirror, looked at me. “He was at Gia’s… Giancomos party in the restaurant in Monaco. Remember? He was talking a lot with Angelo,” I didn’t remember but Gail thought my grunt was an acknowledgement.

“So, what happened?” I asked hoping the `Leo rescue` was what Gail wanted to tell me about. Gail continued, “We danced just seconds, he apologized for what had happened, and then when I said I would use the ladies room he walked with me toward the restroom in the bathhouse. It was locked, in use. I waited nearby, hoisting myself up a few inches to sit on the cement railing that separated the pool from the bath house. Leo sat on the edge of that huge cement planter filled with the bamboo.”

I sensed Gail’s direction and said, “I’ll bet he was getting a good view between your legs.” Gail chuckled, “Yes Ri, he was.”

Then Gail continued recounting what had happened. “I didn’t mind though…his looking, I may have even opened my legs a bit more.”

I thanked him again, I said, “Leo, thanks for what you did there.”

“No big thing”, he responded. He told me an Italian girl would have made a big incident.

I said, “that was what I was trying to avoid, I don’t know how to thank you.” He had mostly been looking at my legs, up my dress when occasioned, but now looked at my face smiling widely. I asked him what was funny. “I know how you can thank me,” he said. His smile was mischievous but I allowed it to continue. I asked him, “You do, and how would that be?” He looked at my legs again, smiling still, and said, “I’d love to be surrounded by that beautiful white patch.” I mocked surprise and said, “Leo, not you too?” He raised both hands palm out, “Sorry, it’s my heart speaking, not my head, ” he made a fist and thumped his chest mimicking his heartbeat. At that moment the door opened, I jumped down and as I entered he asked, “May I wait for you?” Glancing around the edge of the door I said “that would be nice.”

“Of Course,” I said to Gail. “Why shouldn’t he wait,” the latter with a hint of sarcasm.

Gail was now finished at the mirror and sitting on the edge of the bed, rubbing cream on her legs. She continued, “When I came out he was still there, waiting. I told him I had better go look for my husband and he told me you had just walked into the house. I said `thanks, it’s a good thing you’re keeping track of us,` he smiled and with simple forthrightness told me he has not stopped thinking of me since we shook hands at the restaurant. I blushed but I also laughed at his candor.” Gail turned her head to look at me, “for some reason I didn’t feel intimidated by his attention.” As we started for the house I reached to place something into his palm, closing his fingers around it, and said, “please surround yourself, Leo.” He looked at his hand, touched my still warm panties with his other hand, and smiled from ear to ear. In the bathroom, when I considered doing it, I thought it was funny. Now that I actually carried it out I was embarrassed and blushing. Thankfully, he didn’t notice. He offered me the hook of his arm. I placed my arm in his and we walked to the house.

Gail had finally finished her bedtime rituals and pulled back the sheets to join me in bed. Save for her panties, she was naked. That she did not put on a shirt or nightgown was an omen in itself. As she moved the air around her smelled fresh, and when she turned on her side her small breasts hung just low enough to highlight her jutting nipples. She nuzzled close to me. I turned to face her and moved close placing my right arm on her hip. We looked each other in the eye, both smiling, content in silence.

I rubbed lightly over Gail’s hip and back then, touched her cheek and gently squeezed her earlobe, a soft place I love to feel. I rubbed from her shoulders to her lower back, then caressed the cheek of her behind.

“Love me? Gail questioned. I answered, “hooked forever,” then added, “What was it you said you wanted to tell me.” Gail whispered in a breathy way, “Oh yes. I almost forgot. When I went upstairs, just before we left, I opened the wrong bedroom door. Katarina was in there with another girl and a man.” Gail stopped. I waited for what seemed a fair amount of time before I asked, “So? Is that all.” Gail responded quietly, “She was with the girl.” We lay quietly for a few minutes. I broke the silence, “That was a mostly liberated crowd tonight. I wouldn’t be surprised if they were swapping too. I think that’s what Allyson and Patricio had, or still have, in mind.”

“Yes,” Gail whispered, I think that too. She had been touching me while we spoke and I was now hard. Gail had been running her hand up and down my penis then turning her hand backwards and rolling it around. She moved close and placed her left leg over me edging me onto my back, her thigh now resting on my penis.

“Phyllis left us a message, they are coming day after tomorrow,” she stated, then continued. “Do you think Allyson is attractive?” “Yes, she’s attractive… ”

Gail persisted. “Would you like her to touch you like this?” Gail had all five fingers tips lightly rubbing upward strokes just on the head of my penis. “I’d like anybody that does that.” I replied.

Gail leaned over and placed her mouth gently over mine and immediately her tongue was searching. While we were embracing she placed her left leg over and straddled me, still kissing. My penis - now a stone hard cock was pressed against her bush and belly, the under part and my balls pressing directly against her open pussy lips. As we continued to kiss her left hand moved between us and took hold of my cock. She lifted her behind just enough to place me between her legs gently rubbing me across her wetness. When centered at her entrance she pressed down and I felt that tide of warmth and wetness as the head of my cook slowly entered. Gail stopped kissing me and placed her head on the side of my chest, her body still raised above my cock. She began to press down, pausing then pressing again, and then her tell-tale sigh indicated I had fully entered her.

We lay feeling attached with no words spoken. Being in her fully, her hands on my upper arms, her head on my shoulder, hardly moving, was surely as close as I would ever get to feeling as-one with someone.

“Can we sleep like this?” she asked, her voice barely a whisper.

“Only after I come,” I mouthed, while thoughts of the earlier evening were creeping in my mind. I placed my hands on her behind and gently spread her cheeks allowing my finger to brush then rest upon her back hole

“Are there things you still feel uncomfortable doing with me?” I asked. I felt her head move slightly in a sign of no, then she responded, “I don’t think so, why?”

“I’m just wondering out loud,” I answered. “There must be many things we haven’t done together

“Like what?” I didn’t answer and she insisted, still whispering. “What things? I always felt we were pretty good about trying things.”

After some quiet, she added, “Are you talking about me doing something with a Girl?” “No,” I said, “You know that has never been an issue with me.”

Gail offered, “If ever I fancied a girl it would be someone like Gabriela.” As an afterthought she stated, “She like Girls, you know.”

I paused before responding, struggling to hide my surprise and not wanting to discourage Gail from continuing to talk. To keep heightened the feeling of Gail’s wetness around my cock I tightened my behind cheeks and pulled out a little, then entered her again and asked, “Now how would you know she likes girls?”

After a pause she said, “Oh, I heard someone say it.”

“Did Katarina say it.?” I asked. “No,” Gail whispered. After an interval of silence she knew I was waiting for her to say how she had heard it. “Giancomo said it,” she whispered. We had talked very little about him since she had told me of their liaison, and she still did not know I had spied on them. I thought this might be an unguarded moment and she might be more candid. “Did he suggest you be with her?”

“No.” she answered. After a pause, I persisted, “You remember why he mentioned it?”

Gail sighed and I could feel her breath across my nipple, she continued, “I said that I thought Gabriela was so beautiful why would he want to be with…”

I interrupted her before she finished, “I keep telling you love.” I was touching one breast as I spoke, “It’s your soft beauty… innate sensuality. The combination makes you irresistible.” Gail squeezed my arms and rubbed her breast into me. “I love that you think that.” She said.

All the while I was rubbing her behind and pushing my cock gently upwards, into her, then relaxing and pushing again. I continued, “You gave me an idea of what went on with him but not why you thought him the best … your best lover?” Gail raised her head and looked at my face. I peered down at her smiling, touching her caringly, hoping she did not sense my jealousy. Her eyes were searching mine, you’d have thought I’d asked her to solve the riddle of existence.

“He was so different,” she said. “So tender. It seemed like he loved the parts he was loving. When he kissed it was full of passion, he touched every part of my mouth with his tongue. He sucked my lips, it was like my mouth was my whole body for him. He touched my nipples until they were on fire. Not soft, never too hard, I don’t remember but I think he made me come from touching my breasts.” Gail was whispering, sometimes looking at me to make a point, I could tell she was mentally picturing the encounter. I asked, “Did you come from his penetration or from his touching you?”

Gail thought for a second. “I don’t know. It was strange. When he started to fuck me he didn’t go inside. He had his cock flat between my lips and he was pumping up and down bumping and rubbing his cock against my clit. What was really wonderful was when he took his cock in his hand and started rubbing his cock fast over my clit. I was excited by then, ready to come. He rubbed until the exact second I was ready to come and then he stopped. He did that again and again, each time resting by putting his cock inside me. When I pushed against him to fuck me, he didn’t. I wanted to come. Again he rubbed his dick and then he would stop and kiss me. When he was finally ready to let me come I exploded, I kept coming from every little movement… his touching my clit, my behind, his kisses.”

She was telling her story in snippets. Halfway through I was excited and I started moving in and out of Gail as much as possible. Gail responded first by just moving her body while keeping my cock fully inside her then, finally, she lifted her behind and started to move up and down, still relating and reliving the feelings she experienced with Giancomo. Gail was leaned over me looking down, her small breasts hanging - so perfectly proportioned to her slim figure, her jutting nipples attesting to her excitement. She knew I was excited now, and she continued, “When he loved me with his mouth he devoured every part of me. He sucked my clit and the inside of my pussy. When I came he sucked it out of me. When he kissed my back hole I could feel his tongue on every wrinkle, inside and out.” I could feel Gail’s wetness increase, reliving the experience was exciting her as well. She continued her slow steady movement, up and down, my cock bottoming out each time. My hands were on her hips and my eyes were open, watching her.

“Did you plan to be with him when we were all scheduling our afternoon?, I asked, while looking at her.

“No. When we returned no one was here. I stayed in our suite. He came down and knocked on the door. He had a drink for me. When he came in we talked for some time and then… it just happened.” I didn’t say anything to Gail but I didn’t quite remember it quite that way. She continued to narrate. “What got me excited was the kissing. It started that way. I tell you Ri, when he started to touch and kiss my vagina it was like my vagina was all of me… he made love to it… I could tell he loved doing it.” Gail was now moving more forcefully, her breathing signaled that she was close to coming. “Come baby,” she said in a breathy whisper, “do it, cum with me.” I started to lift and rise to her rhythm, Gail was pushing her behind against my thumb pressing against her back hole. I knew the sensation of her pussy getting more wet and hot before she orgasm’d. I was pulling on her nipple, pressing her back hole and meeting each thrust as she started “Ohhh Ri… oh yes baby… do it, do it….ohhh, and Gail started to cum… in torrents. She stopped moving and sat breathless, concentrating on her orgasm, my still hard cock completely secreted inside her. I could feel each throb of her orgasm, each twitch, and though I wasn’t coming I took pleasure with her. Her eyes were squeezed shut, her hair disheveled, her face a mask of bliss. I felt my senses heighten, my breast tightened, my memory recorded the scene I was watching, and I breathed with difficulty at the intensity of the love I felt for her.

Gail was literally wrapped around me, naked, her head on my shoulders, her fingers absentmindedly moving on my chest as if she were counting the hairs. “You didn’t cum Ri, did you? “No,” I answered, “almost actually,” I corrected.

Again she queried, “Any reason?”

“”Yes,” I said, “I was busy thinking how much I love you and I forgot to come.”

“Oh you… bullshit,” she said, and she pulled my chest hair. “Honestly,” I responded, and I knew she did not believe me.

We lay cuddled and touching for five or ten minutes without speaking. Then Gail asked, “Why did you ask me about trying things with you? What were you thinking?”

“Oh, yes,” I answered. That was nothing, just a thought.”

“What thought,” she insisted. “You don’t think nothing thoughts.”

Why not tell her I thought to myself. “Well I was thinking that we have never masturbated for each other.”

Gail looked at me now, for a good while. Finally, she corrected, “Yes we have… in Curacao, in that creepy beach cabana.”

She was right I thought, “Yes, but that has to have been five or six years ago.”

“You said never, didn’t you?, Gail reminded. She continued, “I’ll masturbate whenever you want me to.” After a pause, more thoughtfully, “I’ll do anything for you.

I questioned, “would you?”

“Yes…of course,” she replied.

A good thirty seconds went by before I quietly responded, “Then how come you can’t stay honest with me.?”

Gail rose up and placed a hand on my face. In a concerned tone she whispered, “Oh Ri, you mean about Gaincomo. I know it’s not fair to you. I never plan these things but when it happens…I guess part of the excitement is the spontaneity. I always plan to tell you but somehow it comes out slowly. Even when I’m enjoying it I hate myself for not being more perfect for you.” Gail was almost laying on me now as she continued. “I know you love it when I tell you about what I do, but I found it so difficult when you watched me with Peter. The thought of you watching scares me, I get so afraid you’ll hate me.”

My simple response was “How could I ever hate you,” which I am sure did nothing to ease her misgivings.

Gail had moved her hands from my chest to my semi hard cock and was touching me again. After some moments she moved her head down and started to kiss my cock. I closed my eyes and let her ministrations carry me away. She knew every place to touch, where to lick and how to press. The very thought that it was Gail and that she would take my cum in her mouth or on her cheek, was enough to make me orgasm. She rose up and slide on top of me. In seconds she had guided me back into her warm, still very wet pussy. She rose up and down and pumped forward urging me to orgasm. As I felt the buildup taking control I wrapped my arms around her and in a single motion I flipped her onto her back and braced her legs in the fold of my arms, bending them halfway to her

chest. I started humping and grinding my full length into Gail and she started to groan with each downward thrust. Soon she started intoning, “Do it Ri, do it … cum in me baby,”…and moments later I thrust into Gail to balls length, gasping and groaning as I gushed deep in her belly while she still whispered to me, “Yes baby, yes love, do it.”

We spent a leisurely morning in the hotel with an hour or so on the narrow strip around the pool. It was sunny but a bit too cool in the water so, we mostly talked. We got to talking about a bet I had won that required her to be honest with me, and how well she was adhering to the deal we had made. I didn’t want to bring up a specific issue but I did say that I thought she was faltering, and to my surprise she agreed.

Long ago I had decided that I did not need to place restraints on Gail, she was already overly constrained. When we were at home it was tortuous at times. She would constantly bring up “…what if’s…” which effectively kept us from trying anything flirtatious with anyone else. On one occasion at home we had dinner at the Sheraton Hotel with some business visitors I had in town. When we finished dinner and had said our goodnights, we started out of the hotel when I suggested we stop for a drink at the bar. We sat and listened to a great group singing popular songs in English and Spanish. We were at a table for two, side by side, and facing the band. I noticed one or two in the group regularly staring at Gail. Her legs were demurely crossed so it must have been her beauty that attracted their attention. At one point I placed my hand on her legs and she placed her hand on mine in an automatic reaction. When I later attempted to move her dress she immediately covered her knees again. On a second attempt I was a little more forceful. Gail quickly adjusted again but this time turned to look at me and whispered “Ri.” She was blushing a little and the look in her eyes was of hurt, near to tears. I felt myself the scoundrel, and to this day the picture of her almost teary green eyes is imprinted in my mind. I have decided it’s impossible to push her at home. Here, on holiday, I’ve decided it’s impossible to stop her.

“It’s different when we are here,” she said. “I just feel like here, having fun is accepted.” I commented, “It is, or at least not judged critically.” Gail nodded her head in agreement. I continued, “Then…why do you feel I can’t share with you?”

She looked at me sympathetically, “I do share… some. I think I am always afraid you will think less of me, also…” she hesitated a long time then barely whispered, “it’s more exciting when no-one knows.”

Over the last days Gail had told me bits and pieces of her liaison with Giancomo. I was pleased that her account was as I had seen it happen. I still did not tell her I had spied on them and I was feeling guilty that she was being honest and that I was hiding my misdeeds. Then, maybe because of guilt, maybe meanness, I decided to tell her of past spying I had done. “You know love, I saw you making love with Werner.”

Gail turned to look at me, she literally paled. Her look was stern, concentrated, I knew her mind was churning. When her cheeks started to color again her lower lip looked like it was trembling. I wished I had not mentioned it. Gail whispered, “So long ago… why didn’t you tell me before?”